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I have been working on the following post since November 9th. This is the longest I've ever taken on a post, I know there is a lot there, but if you have 30 minutes or so to kill, I'd appreciate anyone who actually takes the time to check it out. Thanks and I love you.

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This list represents my 20 favorite Gotham-Based villains...

Detective Comics #168 (February 1951)

In the original continuity, an employee looking to steal from the company that employs him, adopts the persona of Red Hood. After committing the theft, which Batman thwarts, the Red Hood falls into a vat of chemical waste. He subsequently emerges with white skin, red lips, green hair, and a permanent grin, later calling himself the Joker.

Now in the more commonly accepted origin, The Killing Joke, we see Joker as a struggling comedian who owes money to the mob. As a way of paying off his debt, they let him wear the mask to seemingly protect his identity as he leads them though the chemical factory that he used to work at. 

Also in early stories, they even talk about other criminals using the Hood to make the police think just one man was committing many crimes.

 
Recently the Red Hood reemerged. It was unknown who was now donning the helmet, but it turned out to be Jason Todd. The 2nd Robin had returned from the dead to become the 2nd Red Hood. It was a stupid twist.

Despite my not liking Todd's return, his death was the most significant event in Batman's life since the murder of the Waynes and because of that, it magnifies the importance of the hood's legend.

 
Red Hood helped to create the rivalry between Batman and the Joker and for that reason, he makes my Top 20.

All-American Comics #61 (October 1944)

In the late 19th century, a wealthy merchant named Cyrus Gold is murdered and his body disposed of in Slaughter Swamp, near Gotham City. Fifty years later, the corpse is reanimated as a huge shambling figure with almost no memory of its past life. Gold murders two escaped criminals who are hiding out in the marsh and steals their clothes. He shows up in a hobo camp and, when asked about his name, one of the few things he can recall is that he was "born on a Monday". One of the men at the camp mentions the nursery rhyme character Solomon Grundy, and Gold adopts the moniker.

Green Lantern and his fellow members of the Justice Society of America tracking Grundy across the country, deposited him on the moon once defeated, where he remains for over two decades. Green Lantern and Solomon Grundy clash many times over the years, though he also squares off against other DC heroes.

 
In The Long Halloween, Grundy and a newly-disfigured Harvey Dent strike up an odd friendship after Dent escapes to the sewers to plot his revenge on Carmine Falcone. Prior to Infinite Crisis, Grundy is manipulated by Gorilla Grodd via mind control into attacking Batman and Superman for President Luthor for the bounty of one billion dollars.

Though, not exclusively a Batman villain, Grundy holds a place in my heart after his involvement in the cartoon SUPER FRIENDS, my favorite as a child. 
 
Solomon Grundy,
Born on Monday,
Christened on Tuesday,
Married on Wednesday,
Took ill on Thursday,
Worse on Friday,
Died on Saturday,
Buried on Sunday:
This is the end
Of Solomon Grundy.

18. The Falcone Family

Batman #404 (March 1987)

The Falcone family, and Carmine Falcone in particular are portrayed as almost completely in control of Gotham City before Batman's arrival. They are major players in Batman: Year One, The Long Halloween, and Dark Victory.

Carmine is credited with ordering the acid thrown at Harvey Dent, in essence creating Two-Face and was featured in BATMAN BEGINS.

Carmine, eventually murdered by Two-Face left his empire in the hands of his daughter. She took over with the intent of using her power to crush Dent, Gordon, and Batman, all of whom she blamed for the death of her father.

Alberto, it turned out, was in fact the serial killer known as 'Holiday', who was the focus of the aforementioned books. Carmine spent much of The Long Halloween trying to find out the identity of Holiday even going as far as to hire the Riddler to investigate.

While used relatively sparingly compared to some other members on this list, they play a huge part in 3 of the best Batman stories ever. Also they lend to the escalation of the more well know super villains, or as they are referred to in Gotham, the 'freaks'. Without starting his career against the Falcones, Batman perhaps would have been overmatched.

Detective Comics #400 (June 1970)

Dr. Kirk Langstrom, a scientist specializing in the study of bats, develops an extract intended to give humans the bat's sonar sense and tests the formula on himself because he is becoming deaf. While it works, it has a horrible side effect: it transforms him into a hideous man-sized bat. The serum also takes away his intelligence, so he goes on a mad rampage.

Talia al Ghul ties up and gags Francine Langstrom, and then threatens to poison her if her husband Kirk does not deliver the Man-Bat formula. After Langstrom gives her the formula, she releases Francine as promised. Talia utilizes the mutagen to turn members of the League of Assassins into Man-Bats.

 
Man-Bat appeared on several of the cartoons and the new LEGO BATMAN, and while he isn't really evil, he does have the Mad Scientist thing going for him.

Batman #386 (August 1985)

Roman Sionis was born into one of Gotham City’s elite families, to wealthy and utterly self-absorbed parents,  moments after his birth, the doctor carelessly dropped him on his head. Roman's parents disliked the Waynes and were quite vocal about it in private with their son. However, to their son's dismay, they continued to associate with Thomas and Martha Wayne and pretended to be friends with the couple, to the extent of literally forcing him to become friends with their son, Bruce. His parents' hypocrisy had a deep impact on him, and he grew to hate and resent them and the "masks" they wore in public.

After his high school, Sionis was given a high ranking position inside his father's company, Janus Cosmetics. There, he met and fell in love with Circe, a working class secretary. His parents didn't approve of the relationship and made it clear that they wanted it ended. Enraged, Roman burned down the family's mansion, killing both of his parents. He then inherited the family fortune & business. Roman eventually ruined Janus Cosmetics by funding a line of face-paint make-up which failed. In desperation, he ordered the chemists to create a product to save the company,  a kind of water-proof makeup. The product was rushed to market without proper testing, and turned out to be a deadly toxin which disfigured several hundred women.

Circe, now Sionis' fiancée, broke up with him in front of his entire staff. At that time, Bruce Wayne offered to bail out the company on the condition that Sionis give up control. Sionis agreed, but was furious at the humiliation he had suffered. He went to the family mausoleum and broke his mother's ebony coffin lid. From a piece of this, Sionis carved a mask, becoming 'Black Mask'.

 He began kidnapping Wayne Enterprizes executives, putting masks on their faces that were coated in the deadly make-up once made by his Janus Cosmetics. He also targeted Circe and forcibly disfigured her with the chemicals in order to force her to reunite with him. Circe would ultimately kill herself, leading Black Mask to replace her with a mannequin that he talked to as if it were a real person.

These kidnappings drew Batman's attention, and he slowly began to dismantle the organization until he finally found Black Mask in the ruins of the Sionis Family home. Black Mask lit the wreckage on fire trying to escape, but was caught in the burning house. Batman was able to save him, but the mask had been burned onto his face and left him disfigured.

Black Mask spent some time in Arkham Asylum, but escaped when Bane assaulted the facility in Knightfall and he began burning down Wayne properties. This time he also kidnapped Lucius Fox, CEO of Waynetech and friend of Bruce Wayne.

When Tim Drake quit his role as Robin in the War Games arc, Batman chose Stephanie Brown, aka The Spoiler, to replace him. Batman quickly discovered that her lack of focus and inability to follow orders made her a danger to herself and others, and fired her. In an attempt to prove herself, Stephanie set it into action a plan was to get all of Gotham's crime lords under the control of Orpheus, an agent of Batman, and therefore under the control of Batman himself. But the Black Mask captured and tortured her, eventually leading to her death. This lead to the Joker wanting to kill Black Mask, for robbing him of the opportunity to kill another Robin.

The two nearly killed each other before Batman intervened. Batman eventually managed to capture Black Mask. However, while being taken to jail, he managed to kill the escorting officer and escape again.


Black Mask rose to become the overlord of the Gotham underworld. He threatened the most important people in Catwoman's life. Still thinking that she adhered to a strict no-kill rule, Black Mask was caught by surprise when Catwoman retaliated by shooting him in the head, killing him.

Black Mask was a bit crazy and totally badass. A perfect addition to gang from Arkham.

Detective Comics #583 (February 1988)

Arnold Wesker was a ventriloquist with multiple personalities, and his puppet was a gangster called Scarface. Under the puppet's psychological influence, Wesker was a dangerous criminal and crime boss.

Born into a powerful Mafia Family, Wesker developed Dissociative Identity Disorder after seeing his mother murdered by an assassin from a rival Family.

Following a barroom brawl in which he kills someone, Wesker is sent to Blackgate Penitentiary. He is introduced to "Woody", a dummy carved by his cellmate Donnegan. Woody convinces him to escape and he kills Donnegan in a fight which scars the dummy, thus resulting in the birth of Scarface.

Wesker lets the Scarface personality do the dirty work, and is dominated by Scarface, who barks orders at him and degrades him. Wesker is unable to enunciate the letter "B" while throwing his voice, and replaces them with the letter "G" instead. For example, Scarface often calls Batman "Gatman."

It is often cloudy as to whether Scarface is an aspect of Wesker's personality, or actually has sentience. In the "The Riddle Factory", it is revealed that a gangster named "Scarface" Scarelli had once been active in Gotham City, though had apparently died long before Batman's era. Wesker's cellmate creates the first Scarface doll from a piece of gallows wood. A Psychodrama reinforces this and shows the dummy to be indirectly responsible for two accidents while separated from Wesker. Scarface also retained his speech impediment while operated by a young boy and seemed to even show awareness of his name during this period.

In many stories, Wesker is accompanied by a loyal bodyguard named Rhino. Rhino is sometimes portrayed as genuinely believing Scarface to be the boss.

The Ventriloquist is one of many villains in the Rogues Gallery to be confined to Arkham Asylum when Batman apprehends him. During the Knightfall saga, after Bane had destroyed Arkham and released its inmates, unable to find Scarface, Wesker uses a sock puppet in his place for a short time. After robbing a toy store, he procures a number of other hand puppets to fill in for Scarface, including one of a police officer which he refers to as "Chief O'Hara" (in reference to the 1960s Batman TV show). Wesker uses a sock puppet until he can find a suitable replacement for Scarface. Later, Scarface and "Socko" are set at odds until a standoff occurs, and the puppets shoot each other, leaving Wesker unconscious and bleeding from two wounded hands.

Batman often uses Wesker and Scarface for info because they are easily intimidated. And while they reign terror over the city, they are sometimes an asset to Batman, much like in the No Man's Land story-arch, which may have been the best long running storyline I've read.

Detective Comics #818, Wesker is fatally shot by an unseen assailant. Scarface is stepped on and its head crushed, it is revealed that Tally Man, an enforcer for the Great White Shark, is responsible for the murder.

Last year, following the murder of Wesker, Peyton Riley took over the duty of voicing Scarface.

Detective Comics #827 (March 2007)

The new female Ventriloquist, called Sugar by Scarface, is a more compatible partner than Wesker. Scarface no longer substitutes "b" with "g" and she is much more compliant with Scarface's brutal methods. She and Scarface seem to have a relationship similar to the Joker and Harley Quinn, as she seems to believe that the dummy truly loves her. When nearly captured by Batman and Harley Quinn, who has a strong dislike for Sugar, borne out of strong feelings of friendship towards her predecessor, she has Scarface say: "Save yourself." Unlike Wesker, who was horrified at any damage to Scarface, Sugar rigs her dummies to explode, using this to cover her escapes. She has numerous identical dummies at her hideout, one of which then becomes the "real" Scarface.

Scarface kidnaps a rival gangster, Johnny Sabatino, and takes Bruce Wayne hostage. While alone, "Sugar" breaks from Scarface and talks to Bruce in what appears to be her 'real' personality. She reveals that she knows Wayne, as she was engaged to a friend of his 'years ago.' This friend was in fact Hush, Tommy Elliot.

 
The ambiguity of Scarface being alive or not makes this character immensely more creepy, a guiding force in the requirements for this list. Though originally a bit of a gag character, Scarface and whomever is carrying him at the time have become darker and more dangerous as Gotham has evolved over the years.

Batman #49 (October-November 1948)

Jervis Tetch is fascinated with hats of all shapes and sizes. Also with the book "Alice's Adventures in Wonderland" and its sequel "Through the Looking-Glass", particularly favoring the chapter 'A Mad Tea Party'.

Jervis made his first appearance, along with Vikki Vale in 1948, and was locked in Arkham not to appear again until 1986. However, during his incarceration, beginning in 1958, another man took up the mantle of 'The Mad Hatter' claiming that in fact, HE was Jervis Tetch.

Detective Comics #230 (April 1956)

This imposter, unlike the original, was sane and sported a gaudy mustache. He was primarily a thief, apparently obsessed with completing his private collection of hats from all nations, cultures, and historical periods. He often constructed various weaponry concealed inside his hats like flamethrowers and buzzsaws. He was the inspiration for the version of the character seen on the 1960 TV show.

It was revealed that he was in fact an impostor when the real Jervis Tetch returned. The real Hatter claimed to have killed his impostor, but the fake Mad Hatter appeared one last time in 1987, where he ended up being beaten by Batman and has never appeared since.

After his return, Tetch escapes from Arkham in time for Halloween, and makes his home in an old mansion that had been abandoned after a gruesome murder years before. Retreating deeply into his delusions about Wonderland, Tetch offers sanctuary to runaway children, asking them in return to dress up as characters from Alice in Wonderland and attend his tea parties. At these parties he serves them drugged tea to keep them sedated.

 Around this time, Barbara Gordon comes to Gotham, having been adopted by her uncle, Commissioner James Gordon, following the deaths of her parents. Barbara sneaks out against orders, and goes to Gotham Park, where she soon finds herself being chased by a group of masked men with knives. The group surrounds her, with the intent of rape. The Hatter appears and scares the men away and he takes Babs to his "Wonderland", where she is expected to play the role of Alice. When she wont play along, a rescue by Jim Gordon becomes needed.

According to Dr. Blaylock of Arkham Asylum: "Jervis is a paranoid schizophrenic...And he's obsessive-compulsive, and highly delusional. He's got an immature self-image, so he identifies more with children than adults. Oh and he's a genius, too."

  
Something about the Wonderland aspect interests me here. Since the modern era of comics has started, contrary to the Animated Series we all watched as kids, Hatter has become dark and creepy. He fits in nicely at Arkham.

Detective Comics #40 (June 1940)

The original Clayface was Basil Karlo. He is an actor who is driven mad when he hears of a remake of the classic horror film he had starred in, The Terror. Donning the mask of the film's villain, Clayface, he embarks on a murder spree among the cast and crew of the remake. He had a famous feud with the Joker and eventually was sent to a prison hospital where he lived for years.

Detective Comics #298 (Dec, 1961)

A second Clayface emerges in 1961, this time with shape-shifting abilities. Matt Hagen, a treasure hunter, finds a mysterious radioactive pool of protoplasm in a cave. Immersing himself in it, he is transformed into a malleable clay-like form which could be shaped into almost anything he desires. This is only a temporary effect, however, requiring him to return to the pool periodically in order to maintain use of his powers. Hagen is ultimately killed by a shadow demon during the Crisis on Infinite Earths.

 
The third Clayface, Preston Payne, suffering from hyperpituitarism, worked at S.T.A.R. Labs searching for a cure. He obtains a sample of the then-living Matt Hagen's blood, and isolates an enzyme which he introduces into his own bloodstream. Although he is briefly able to shape his own appearance, this effect is short-lived: while on a date, his flesh begins to melt, and when he touches his horrified girlfriend, she completely melts.

 Payne builds an exoskeleton anti-melting suit to prevent himself from touching anyone, but he learns that he needs to spread his melting contagion onto others to survive (he feels pain if he doesn't melt anyone). During this time his mental health starts to slip as he falls in love with a wax mannequin he names "Helena", thinking she is the only woman immune to his touch. After another breakdown, he thinks Helena enjoys watching men "fighting over her" when he battles Batman yet again in front of the wax doll. Although he doesn't give her up, he keeps her in Arkham Asylum, saying "we're both too polite to admit divorce, but she can't live forever."

 The fourth Clayface, Sondra Fuller, also known as Lady Clay, was a member of Strikeforce Kobra who is transformed into a shape-changer by her employer Kobra's technologies, a process to which she agrees to become a subject because she hates her own face. She possesses identical abilities to those of Matt Hagen, but they are permanent, without the requirement for a source of protoplasm.

These 4 Clayfaces join together to form THE MUD PACK. Although lame, it does accomplish something great. Basil Karlo dupes his allies into giving him their powers and he becomes Ultimate Clayface. Thus negating any need for further mention of the previous 3 incarnations as well as 5, 6, and 7. Ultimate Clayface is the Clayface we are familiar with now.

 
This is the Clayface that we have had in all modern versions. He is ruthless and dangerous and played a major part in No Man's Land when he imprisoned Poison Ivy. Batman agreed to rescue her, but she had to grow food for the city, which was vital following Gotham's devastating earthquake.

Clayface is one of Batman's oldest villains, and proved himself a suitable nemesis time and time again, even squaring off against the Joker on multiple occasions.

12. Killer Croc

Detective Comics #523 (February 1983)

Waylon Jones is born with a medical condition that caused him to grow progressively more like a crocodile. In the comics his intelligence level has varied from competent schemer to berserk monster. In his original appearances, he resembled a powerfully-built man covered entirely in green scales. However, his disease has slowly robbed him of all identifiable human traits. In his most recent appearances, he has an enlongated snout and tail.

Croc is afflicted with regressive atavism, meaning he has inherited some of the traits of ancestral species of the human race, such as reptiles which can regenerate lost limbs. His skin resembles the condition, epidermolytic hyperkeratosis, however in his case his entire epidermis (and physiology to an extent) actually is reptilian and not an irregular disfigurement. His skin has hardened to the point where it is invulnerable to most forms of abrasion and even high caliber weapons fired from a distance. He possesses super strength, able to rip a large bank vault door right off its hinges with ease. He has superhuman regenerative powers, able to heal even lost limbs.

Over time the primal reptilian part of his brain gains more control of his psyche. He possesses superhuman reflexes and speed. Croc also possesses the superior senses and underwater capabilities of his namesake.

 
Croc is a somewhat sympathetic character at times. He was once broken out of Arkham by Swamp Thing and invited to come live in the swamp and be free, but ultimately wound up back in Gotham.

Croc played a big part in the beginning of the Hush saga, where his mutation had begun to advance beyond recognition. Croc is a savage killer and has often been forced back into Arkham by the Caped Crusader.

Croc appeared regularly in the cartoons as well as video games and in the last 25 years has become a staple of the famous Rouges Gallery.

Croc is one of the more savage villains on this list, with no qualms about slaughtering people. Though is also somewhat more practical than some of the others as well. He is not tied down by any sort of gimmick. No coin, no riddles, no hats, and no umbrellas. He is more often than not motivated by money, rather than just killing Batman like some of his colleagues.

Batman: The Animated Series "Joker's Favor" (September 11, 1992)

(Harley was the only character on the list that was not created for the comics, but for the cartoon. She proved so popular that she was introduced into the comic book canon.)

She was once psychiatrist Dr. Harleen Quinzel, but fell head over heels in love with the Joker after spending just 15 minutes with him inside Arkham Asylum. She developed an obsession with him, and turned to crime to win his love. Quinn decided that the only way to make the Joker love her is to kill the Batman, which she attempts to do by feeding him to a school of piranhas. The Joker, upon arrival, is infuriated that Harley would try to kill Batman herself and nearly kills Quinn.

Batman saves her and confronts the Joker, taunting him, "I have to admit she came a lot closer than you ever did... 'puddin'."

Joker attacks Batman, & after a vicious fight, he sends Joker plunging to his apparent death. Once again in Arkham, Quinn realizes that the Joker had merely been using her, and renounces him forever. That is, until she receives a "get well" bouquet of flowers from him, suggesting he survived his fall, and promptly falls in love again.

Harley later helps the Joker with a plan to kill all his former henchmen, unaware that the "punchline" to the scheme is her own death. Upon realizing this, she shoots him in the shoulder.

When she resurfaces, she is still a borderline psychotic, but has apparently reformed. Harley has spent the last year applying for parole, only to see her request systematically rejected by Bruce Wayne, the layman member of Arkham's medical commission. She is kidnapped by Sugar, the new female Ventriloquist, who offers her a job; Harley turns the job down out of respect for the memory of Arnold Wesker, and helps foil the imposter's plans. Although Sugar escapes, Bruce Wayne is impressed with Harley's effort at redemption, and agrees to her parole.

Harley's relationship with the Joker is one of the most complex in the DC Universe. While he often abuses her, sometimes near the point of death, there are as many instances that show a mutually affectionate side to their bizarre relationship. Certain stories imply that the Joker wrestles with the confusing reality of actually caring for someone, giving in to the sentiment more or less at times depending on his mood or state of mind.

Joker however is not the only major villain that Harley regularly associated with. During NO MAN'S LAND, the Joker attempts to kill her, but she is rescued and nursed back to health by Ivy, and now they often work work together. She was also good friends Arnold Wesker prior to his death.

Harley has vaulted up quickly as one of the most popular villains in Gotham. Her dynamic with the Joker seems to constantly draw me to her, as she shows us to see a different side of him. She also has the same kind of psychotic personality, but turns to a little kid once caught as if her dynamic with Batman is nothing more than a game to her.

Batman: Vengeance of Bane #1 (January 1993)

The origin of Bane is similar to that of the Count of Monte Cristo, Edmond Dantès. Born to serve the life sentence of his father, Bane's childhood and early adult life are spent behind the walls of Peña Duro, an infamous prison located in Santa Prisca. Though imprisoned, his natural abilities allow him to develop extraordinary skills within the prison's walls. He reads as many books as he can get his hands on, builds up his body in the prison's gym, and learns to fight in the merciless school of prison life. Despite his circumstances, he appears to have found teachers of various sorts during his incarceration, ranging from hardened convicts to an elderly Jesuit priest, under whose tutelage he apparently receives a classical education. Bane murders this priest upon his return to Santa Prisca years later. However, he commits his first murder at the age of eight, stabbing a criminal who wanted to use him to gain information about the prison.

During his years in prison, Bane carries a teddy bear he calls Osito, whom he considers his only friend. It is revealed that Osito has a hole in his back to hold a knife that Bane uses against anyone who bullies him.

Bane ultimately establishes himself as the "king" of Peña Duro prison. The prison's controllers take note and, eventually, force him to become a test subject for a mysterious drug known as Venom, which had killed all other subjects. It nearly kills him at first, but he survives and finds its effects enhance his physical strength, although he needs to take it every 12 hours or he would suffer debilitating side-effects.

Years later, Bane escapes Peña Duro, with ambition to destroy Batman, whom he had heard tales of while serving his sentence. He is fascinated with Gotham City as, like the prison, it is a place where fear ruled. Bane is convinced that the demonic bat that haunted his dreams since childhood is a representation of the Batman.

Knightfall is what followed.

Aware that a direct assault on Batman would be foolish, Bane destroys the walls of Arkham Asylum, allowing its deranged inmates, including the Joker, the Scarecrow, the Mad Hatter, and The Ventriloquist to escape into Gotham City. Batman spends three months rounding them up, running himself to exhaustion. Batman returns to Wayne Manor, where Bane awaits him. They fight in the Batcave, Bane breaks Batman's back and leaves him paraplegic, thereby having been the only man to have "Broken the Bat".

 
Bane slightly edges out Harley as the newest character on the list.

If you've only seen the movies, you might wonder how the hell he made this list. But the abortion of a movie that was 1997's BATMAN AND ROBIN greatly misrepresented Bane as he was portrayed as a mindless thug. He was also in the Animated Series and the pathetic animated movie Sanchez and I rented, BATMAN: MYSTERY OF THE BATWOMAN, where he was voiced by Hector Elizondo.

Knightfall however is the only reason he cracks the Top 10 on here. The act of breaking Batman's back put him in a class by himself, however in the 14 years since, he has done relatively little. He was involved in No Man's Land which I loved, but did so little it barley cancles out his movie appearance.

 Detective Comics #140 (October 1948)
 
The Riddler is so deeply ingrained into his own personality that he is virtually powerless to stop himself from acting it out. He cannot simply kill his opponents when he has the upper hand; he has to put them in a deathtrap to see if he can devise a life and death intellectual challenge that the hero cannot solve and escape. However, unlike many of Batman's themed enemies, Riddler's compulsion is quite flexible, allowing him to commit any crime as long as he can describe it in a riddle or puzzle.

Some have suggested that the Riddler's compulsion stems from parental abuse that he endured as a child. After Edward got high scores on some important tests in school, his father, unable to grasp the fact that his son was brilliant, beat him out of envy. This left him with a strong internal desire to tell the truth, and prove his innocence. This desire manifests itself in the form of his obsession with riddles. Others have suggested that his madness, as well as his descent into crime, have roots in a yearning to rise above the anonymity that he possessed as a youth.

In The Long Halloween, the Riddler appears when Carmine Falcone hires him to figure out who the Holiday Killer is. Despite giving several reasonable theories as to who is behind the killer's identity, Falcone eventually loses his patience and orders his daughter, Sophia, to force the Riddler to leave. Upon exiting Falcone's office, the Riddler is attacked, but for some reason left alive, by Holiday. The attack coincided with the holiday of April Fool's. He plays a slightly larger role in the story's sequel, Dark Victory, in which Batman turns to him to figure out the significance of the lost games of hangman that are left at the scenes of the Hangman killer's crimes. He later showed up as a member of Two-Face's jury during the Hangman's trial.

In the one-shot "Riddler and the Riddle Factory", the Riddler becomes the host of an underground gameshow that focuses on digging up dirt on celebrities. Many of the famous people that he humiliates end up committing suicide shortly afterwards, suggesting that perhaps the Riddler did more than just inspire their deaths. In the end, his actions turn out to be a front for his attempts to find the hidden treasures of "Scarface" Scarelli, a Gotham City gangster who lived long before Batman's reign of crimefighting.

The Riddler, reformed, worked as a private consultant on the murder of a wealthy socialite. Hired by the socialite's father, he proves that a photo of Bruce Wayne apparently implicating him in the crime depicts an impostor and briefly works with Batman to investigate the crime.

In Detective Comics #837 Riddler, now a P.I. is hired by Bruce Wayne to track down an experimental drug developed by Wayne Enterprizes currently being tested for muscle stamina and cellular regeneration which has been stolen by a lab assistant named Lisa Newman. He discovers that Newman is staying at the same Athenian Women's Help Shelter as Harley Quinn. With Harley's help he defeats Newman and returns the drug to Wayne Enterprizes, earning Batman's trust for the time being.

 
Riddler is one of the most well know Batman villains playing a major part in the 1966 movie. In the movie he was shown as an equal to the Penguin and Joker, though he is seldom seen in that same light now.

A song based on The Riddler was performed by Method Man and was featured on the BATMAN FOREVER SOUNDTRACK. There is also a song by Frank Gorshin in which he sings about riddles and his obsession with them. Also The Riddler makes an appearance in the music video of the 1984 song 'The Riddle' by Nik Kershaw.

The Riddler, though a more interesting character now, has been living on the laurels of the TV show for years. He really isn't an A-List villain anymore, which Ivy, the Joker, and Batman are all quick to point out to him often. His recent transformation into a PI is interesting, but not menacing.

 Detective Comics #58 (December 1941)

Born Oswald Chesterfield Cobblepot, the Penguin is bullied as a child for his short stature, obesity, and beak-like nose. Several stories relate that he was forced as a child to always carry an umbrella by his over-protective mother, due to his father dying of pneumonia after being drenched in a downpour. These traits make him an outcast in his rich, high society family; their rejection drives him to become a criminal. In keeping with his family's tradition of wealth, the Penguin lives a life of crime, yet executes it with his own self-proclaimed class and style. In keeping with his pretensions of being a refined gentleman, he also prefers to wear formal wear such as a top hat, monocle, and tuxedo during his jobs.

The Penguin received his alias from a childhood nickname, bestowed by his peers, who teased him because of his grotesque appearance and love of birds. Retellings of his origin suggest he also suffered from some sort of hip ailment, which caused him to waddle when he walked, though he shows no signs of suffering from this affliction today.

Some comics suggest that he tried to abandon the nickname, which he hates, but it has been permanently brought into popularity by his high-profile criminal career. He has cashed in on its popularity with his Iceberg Lounge nightclub in Gotham City.

Unlike most of the Batman villains, the Penguin is in control of his own actions and perfectly sane, features that serve to maintain a unique relationship with his archenemy. This has extended into the current situation with the Penguin ceasing his direct involvement in crime, instead running his nightclub that is popular with the underworld. As such, he is an excellent source of information on crime, so Batman grudgingly tolerates his operations. The Iceberg Lounge is often both the center of criminal activity and the hottest nightspot in Gotham City.

However, the entrepreneurial Penguin is often fencing stolen property or arranging early furloughs for incarcerated former criminal associates - for a hefty fee, of course - on the side. During the storyline "No Man's Land", when Gotham City is nearly leveled by an earthquake, he stays behind when the US government shuts down and blockades the city. He becomes one of the major players in the mostly-abandoned and lawless city, using his connections to profit. One of these connections is discovered to be Lex Luthor and his company, LexCorp. The Penguin keeps a presence in Gotham as it is rebuilt, mostly due to the efforts of Lex Luthor.

The Penguin may be 2nd only to the Joker as the best known member of Batman's Rouges Gallery. He was a major player in the 1960's series as well as all the cartoons and 1992's BATMAN RETURNS.

ROCKY'S Burgess Merideth and IT'S ALWAYS SUNNY IN PHILADELPHIA star Danny DeVito both famously portrayed Oswald Cobblepot.

Despite the Penguin's prominence, unlike the Joker, he hasn't been the center of any major storylines in quite sometime. Much like The Riddler he has moved away from his super-villain status.

Though still a criminal, Penguin is almost more valuable to Batman because of his past relations than much of the GCPD. Cobblepot's constant willingness to roll over on his past associates and his vast information gathering network allow him to trade favors with the Dark Knight regularly.

 
Originally he was much higher on my list based on the 60's TV version of the character, but I really can't justify that ranking since his change in stature from Super-Villain to Underworld Crimelord. He now, much like The Riddler seems to be on the outside looking in more often.

First Appeared: Batman #121 (February 1959)

From the time of his first appearance in 1958 onward, Mr. Freeze was portrayed as one of many "joke" villains cast as stock enemies of Batman. Originally called Mr. Zero, the producers of the 1960s Batman television series renamed him Mr. Freeze and the name quickly carried over to the comic books. Nearly 30 years later, in the Batman: The Animated Series episode "Heart of Ice", he was made into a more complex, tragic character. This version of Mr. Freeze was enthusiastically accepted by fans, and has become the standard portrayal for the character in most forms of media, including the comic book series itself, which previously had the character casually killed off by the Joker. Freeze was resurrected in the comic after the episode aired.

 As a child, Victor Fries was fascinated by freezing animals. Horrified, his parents send him to a strict boarding school, where he is miserable, feeling detached from humanity. In college, he meets a woman named Nora, whom he falls in love with and ultimately marries. Nora later falls terminally ill & Fries takes on a job working for a large company run by the ruthless Ferris Boyle. Victor discovers a way to put Nora into cryo-stasis hoping to sustain her until a cure could be found. Boyle finds out about the experiment and attempts to have her brought out of stasis, overruling Victor's frantic objections. A struggle ensues, in which Boyle kicks Fries into a table full of chemicals and leaves him for dead. Victor survives, but his body temperature is lowered dramatically, he can now only live at sub-zero temperatures, forced to wear a special refrigerating suit to stay alive.

His first act as a costumed criminal is to take revenge upon Boyle, a plan with which Batman interferes. Mr. Freeze fires his freeze-gun at Batman, but he dodges, causing the beam to shatter Nora's capsule. Freeze blames Batman, and swears to destroy whatever the Dark Knight holds dear. Freeze's crimes tend to involve freezing everyone and everything he runs into. In addition, he hardly ever forges alliances with the other criminals in Gotham, preferring to work alone, although he has worked as a hired enforcer/hitman for the Black Mask.

During his time with the Secret Society of Super Villains, he fashions for Nyssa al Ghul a sub-zero machine in exchange for the use of her own Lazarus Pit. He attempts to restore Nora to life, however she returns to life as the twisted Lazara, and blames her husband for her plight. She estranges herself from him. He is usually imprisoned in Arkham Asylum when apprehended by Batman, as it is the only facility in Gotham that can accommodate his medical requirements for a refrigerated cell.

 In darker incarnations of the Batman mythos, Mr. Freeze's obsession with ice stems from personal tragedy, and his crimes are inspired by his desire to make the rest of the world as miserable as he is. He freezes areas around him using special weapons and equipment, most notably a handheld "cold gun". His refrigeration suit grants him superhuman strength and durability, making him a powerful villain in Batman's rogues gallery. He has even shown to be a formidable opponent for Superman. Some interpretations suggest that because Fries has been soaked in the serum he intended to use for cryo-preservation, his age progression has slowed drastically.

In Batman Beyond, which is set 40 years in the future, Bruce Wayne still has one of Mr. Freeze's guns in the Batcave. The episode "Meltdown" reveals that the disembodied head of Victor Fries has survived though the years thanks to the cryogenics technology, and he is now essentially immortal. Dr. Stephanie Lake uses Mr. Freeze as a test subject and creates a clone body for him. Given a normal life back, Fries tries to right some of the wrongs he committed as a criminal. However, the new body soon begins to revert to the same sub-zero biology. Lake betrays Fries, hoping to learn more from an autopsy, but he escapes, recovers an old suit of sub-zero armor, and becomes Mr. Freeze again. He seeks revenge by killing Lake and by attempting to blow up up a Wayne-Powers complex with both himself and Derek Powers in it, but Batman foils the plan. Freeze redeems himself by saving Batman from Powers, now mutated into the supervillain Blight, but apparently perishes when he refuses to escape the exploding complex with Batman.

Mr. Freeze's often refusal to associate with some of the other Gotham elite, makes him different. He doesn't feel as though he should be considered with them as his motivation differs so drastically. Not to mention almost every time he has teamed-up with another villain, he has been betrayed.

The idea of being driven to this point by the pain caused from losing his wife, hits a cord with me. He is a somewhat sympathetic character, but he is so far gone his heart has frozen over and no longer wants to be happy. The idea that he is motivated by as desire to make everyone as miserable as he is almost scary. He is fuels entirely by hate and destain for all around him.

6. Poison Ivy

Batman #181 (June 1966)

Pamela Isley grows up wealthy in Seattle, but with emotionally distant parents. She studies advanced botanical biochemistry at a university with Alec Holland (aka Swamp Thing) under Dr. Jason Woodrue. Isley, a timid, shrinking violet, is easily seduced by her professor. Woodrue injects Isley with poisons and toxins as an experiment, causing her transformation. The experiment nearly kills her twice and succeeds in driving her insane. Later Woodrue flees from the authorities, leaving Isley in the hospital for six months. Enraged at the betrayal, she suffers from violent mood swings. When her boyfriend has a car accident after mysteriously suffering from a massive fungal overgrowth, Isley drops out of school and leaves Seattle, eventually settling in Gotham City.

(Here is Alec Holland, who later became the Super-Hero Swamp Thing, and Dr. Jason Woodrue, who turned out to be the villain Floronic Man who would battle the JLA multiple times, and once teamed up with Batman to save the live of Solomon Grundy)

Ivy begins her criminal career by threatening to release her suffocating spores into the air unless the city meets her demands. Batman, who appears in Gotham that very same year, thwarts her scheme, and she is incarcerated in Arkham Asylum. From this point on, she has a kind of obsession with Batman, he being the only person she could not control. Over the years, she develops plant-like superpowers, the most noticeable being a lethal toxin in her lips, as she is able to literally kill with a kiss.

In subsequent issues, she states that she only started a life of crime to attain sufficient funds to find a location to be alone with her plants, undisturbed by humanity. A few years later, she attempts to leave Gotham forever, escaping Arkham to settle on a desert island in the Caribbean. She transforms the barren wasteland into a second Eden, and is, for the first time in her life, happy. It is soon firebombed, however, when an American-owned corporation tests their weapons systems out on what they think is an abandoned island. Ivy returns to Gotham with a vengeance, punishing those responsible. After being willingly apprehended by Batman, she resolves that she can never leave Gotham, at least not until the world was safe for plants. From then on, she dedicates herself to the impossible mission of "purifying" Gotham.

At times, Ivy demonstrates positive, even maternal traits. During No Man's Land, when Gotham City is destroyed by an earthquake, rather than fight over territory like most of Batman's enemies, she holds dominion over Robinson Park and turns it into a tropical paradise. Sixteen children who are orphaned during the quake come to live with her, as she sympathizes with them. That winter, Clayface (Basil Karlo) pays Ivy a visit, hoping to form a bargain with her. This would entail her growing fruits and vegetables, having the orphans harvest them, and him selling the produce to the highest bidder. She wants nothing to do with the plan, and she attempts to kill him with a kiss. Clayface overpowers her however, and imprisons Ivy and the orphans for six months in a chamber under the park's lake. He feeds her salt and keeps her from the sun to weaken her.

Eventually, Batman comes and discovers the imprisoned orphans and Ivy. The two agree to work together to take Karlo down. Batman battles Clayface and instructs Robin to blow up the lake bed above, allowing the rushing water to break apart the mud, effectively freeing Ivy. She fights Karlo, ensnaring him in the branches of a tree and fatally kissing him. She then proceeds to sink him down into the ground, where he becomes fertilizer for Ivy's plants. Batman, originally intending to take the orphans away from Ivy, recognizes that staying with her is what is best for them, and they remain in her care until the city is restored. Also, as part of a bargain to keep her freedom, Batman arranges it so that Ivy provides fresh produce to the starving hordes of earthquake survivors. Soon after, Ivy finds Harley Quinn, who had almost been murdered by the Joker, among the debris of the earthquake and nurses her back to health. The two have been best friends and partners-in-crime ever since.

(The HUSH Storyline, what got me back into comic books.)

Later on, she is manipulated by the Riddler and Hush. Her task is to hypnotize both Superman and Catwoman; however, she abandons Catwoman to be killed by Killer Croc, and Batman is able to keep Superman busy in a fight long enough for the Man of Steel to break out of the spell. Soon afterwards, the Riddler, who is being chased and attacked by Hush, approaches Ivy and seeks her protection. Ivy, who is angered by the earlier manipulation, battles the Riddler and dominates her opponent, humiliating Riddler and temporarily breaking his spirit.

Now her control over flora has increased, referred to as being on a par with Swamp Thing or Floronic Man. She has resumed her crusade against the corporate enemies of the environment with a new fanaticism, regarding Batman no longer as a main opponent, but as a 'hindrance'. Batman discovers that Ivy has been feeding people to a giant plant which would digest the victims slowly and painfully. She refers to these murders as a "guilty pleasure". In an unprecedented event, her victims' souls merge with the plant, creating a botanical monster called Harvest, who seeks revenge upon Ivy. With the intervention of Batman, however, she is saved. Ivy is left in critical condition, and the whereabouts of Harvest are unknown

 
A major player in the Animated Series and one of the lead villains in the abortion...err...BATMAN AND ROBIN, Ivy has become Batman's #1 female villain since Catwoman crossed sides. It is a shame that BATMAN AND ROBIN was so bad because Uma might be my favorite actress...should have been good.

Ivy, being the main female advasary, has maybe the worst mood swings of anyone in Gotham, I guess she is just always on the rag...Regardless she is one of the most unstable and dangerous personalities in all of Gotham.

Batman #232 (June 1971)
 
Ra's Al Ghul is the single most mysterious and cunning of Batman's foes. He does not associate with the criminally insane group of the rogues gallery. Ra's Al Ghul is a criminal like no other. No one knows exactly when he was born, but he claims to have been alive for over 600 years. His name translated means "The Demon's Head."

Ra's heads a worldwide criminal organization, whose mission is to purify a polluted planet, and restore nature to the dominion abridged by the human race, ultimately creating a better world where he would rule. He will use whatever means and force necessary to achieve his twisted vision of a new utopian society.

Ra's madness originates in the unique power source which maintains his body's appearance, The Lazarus Pit. It is a substance of unknown elements which replenishes the body, like a fountain of youth. The side affects however are spells of sheer madness. Being addicted to this substance for so long has dried any bit of morals and values for Ra's Al Ghul. He views himself as above any preset laws which are governed by mankind.

His interest in Batman arose when he felt the Lazarus Pits affect was dwindling. Ra's feels he needs a male to be his successor. Since his only offspring is his daughter Talia, he has to choose a male to marry her that is worthy of becoming ruler of his vast empire. Ra's proves his resourcefulness to Batman by meeting the "Detective" as he calls him, in his own Batcave confirming that he knows his secret. Upon implementing many tests to prove whether Batman was worthy of becoming his successor, Ra's knew immediately he had found the one. But Batman refused numerous times, and thus Ra's believes that since he will not be with him, they must be against each other, as enemies. He is highly sophisticated and can be quite hypnotic.

In the graphic novel Son of the Demon, Ra's enlists Batman's aid in defeating a rogue assassin and warlord, Qayin, who has murdered Ra's' wife Melisande. During this storyline, Batman marries Talia and she becomes pregnant. Batman is nearly killed protecting Talia from the assassin's agents. In the end, Talia ends her relationship with Batman, unwilling to put him in danger. She claims to have miscarried and the marriage is dissolved. The child is eventually born and left at an orphanage, taking the name Ibn al Xu'ffasch. Two Elseworlds stories, Kingdom Come and Brotherhood of the Bat, feature two alternate versions of Ibn as an adult, coming to terms with his dual heritage. He has recently reappeared under the name Damian, living at Wayne Manor for a short time.

Rs'a played a prominent role in BATMAN BEGINS as well as several episodes of the Animated Series. He views the 'Detective' as the only man that is worthy to be his heir, but years of the Lazarus Pit rotting his mind has driven him so insane that he will not accept Batman's refusal.

Because he is on such a different level from the other villains, it makes him unique. He couldn't care less about money and majority of his attempts to kill Batman are actually just tests he knows Batman will survive. He really does think he can make the world better and he doesn't care how many people he has to kill to get there.

World's Finest Comics #3 (Fall 1941)

GOLDEN AGE: In World's Finest #3, during the Golden Age of Comic Books, the Scarecrow is first introduced as Jonathan Crane, a professor of psychology. He turns to crime after he is fired; an expert in the psychology of fear, he had fired a gun in a classroom full of students to illustrate a point. The only thing revealed about his early life is that, as a child, he had liked to frighten birds. His modus operandi is to use his Scarecrow persona and threaten his victims into doing whatever he wants. In terms of his costume, he merely wears a ragged black hat, trenchcoat and mask, and wields a tommy gun.

His first crime involves businessman Paul Harold. The Scarecrow kills him and becomes a media sensation. Bruce Wayne, who happens to be a patron and trustee of the university, investigates the matter as Batman and discovers Crane's disturbing behavior and forced resignation, and Crane is sent to Gotham State Penitentiary in 1941.

In 1943, in Detective Comics #73, he escapes from jail and forms a gang of criminals to do his bidding. This version of the Scarecrow was much like other gimmick villains in that he based a lot of crimes around nursery rhymes and words that rhymed with "hat". This is the last appearance of the Golden Age Scarecrow until a flash back written in 1983, and set in 1955. It is then revealed that he developed a hallucinogenic chemical toxin that could be used to invoke deep phobias within those who breathe it in. When Batman tries to intervene, he is affected by the toxin and hallucinates that all of his allies have disappeared. Feeling he has no one else to turn to, he confides in an old enemy, Catwoman, to help him stop Crane, and she is successful in helping stop the Scarecrow and getting Batman over his delusions. Exactly what happens to Crane is not revealed because of the revelation that the Golden Age universe is actually Earth-Two, in DC's SUPER CONFUSING 'Multiverse'.

 
The Silver Age version, first appearing in 1967, seen above on the cover of Batman #189, is a recurring villain in the later Batman stories. He is a frequent member of the Injustice Gang. Ironically, in this Earth-One incarnation, he has a pet magpie named Craw, while the post-Crisis Crane has a phobia of birds.

Entering the Modern-Era of comics, in 1989, Crane's origin story was greatly expanded on as part of the Batman: Year One continuity. He becomes obsessed with fear and revenge from being bullied throughout his childhood and adolescence for his lanky frame and bookish nature, especially his resemblance to Ichabod Crane from Washington Irving's The Legend of Sleepy Hollow. At the age of 18, he brandishes a gun in his high school parking lot during the senior prom. Dressed in the ghoulish scarecrow costume that would later become his trademark, Crane causes the head bully, Bo Griggs, and his girlfriend, Sherry Squires (who had rejected Crane), to have an automobile accident which paralyzes Griggs and kills Squires. Crane discovers a savage delight in literally frightening people to death.

He grows up to become a professor of psychology at Gotham University, specializing in the psychology of fear. As in the original version, he loses his job after he fires a gun at his students to prove a point; in this version, he injures a student. After his dismissal, he kills the regents who fired him and becomes a career criminal. Following this, he transfers to Arkham Asylum and becomes a psychiatrist, where he performs cruel, fear-induced experiments on his patients. He takes the moniker "the Scarecrow", the favorite taunt of the hated bullies, as part of his revenge.

Batman/Scarecrow: Year One, (above) expands upon the earlier origin story. The novels explains that Jonathan Crane is born out of wedlock and also suffers severe abuse from his fanatically religious great-grandmother. His father takes off before he is even born, and his mother does not show any love or affection towards her son. He develops a taste for fear and an affinity for crows when his grandmother locks him in a dilapidated church full of birds. The story also shows Crane murdering his grandmother.

In the Knightfall storyline, Scarecrow is one of the prisoners that escaped from Arkham after Bane blows it up. He decides to become partners with The Joker in terrorizing the mayor. At Scarecrow and Joker's hideout, the Scarecrow attempts to poison Joker with his fear toxin, only to find that it has no effect on The Joker, who in turn beats Scarecrow with a chair. He is then sent back to Arkham.

Recently, the Scarecrow has decided to stop using his typical fear gas, as he feared that other Arkham inmates are right that he is nothing without them. Instead relying on his training as a psychologist, he drives two inmates to suicide using only his words, also apparently terrifying the rest of Arkham's inmates. After manipulating the guards to freeing him, Crane embarks upon a string of murders, terrifying Gotham without using his trademark gimmicks.

 
Scarecrow has blossomed in other forms of media. The Animated Series featured him regularly as well as appearances in both of the Nolan Batman movies. He was a major villain in BATMAN BEGINS, and appeared in the beginning of THE DARK KNIGHT. He also appears in the new LEGO BATMAN game.

Scarecrow optimizes what a true Gotham villain should be. He works based on fear, like Batman. He is competitive enough with the other Rouges to not leave Gotham, and he is a cold blooded murderer.

Detective Comics #33 (November 1939)

Now alot of you may be thinking, "Who the fuck is Joe Chill?" Well, Joe Chill indirectly created Batman, and thereby indirectly created half the characters on this list. Chill is the man who murdered Thomas and Martha Wayne in Crime Alley all those years ago.

Batman's origin story is first established in a sequence of panels in Detective Comics #33, but the mugger is not given a name until Batman #47 in 1948. In that issue, Batman discovers that Joe Chill, the small-time crime boss he is investigating, is none other than the man who killed his parents. Batman confronts him and reveals his secret identity. Chill, frightened, seeks protection from his henchmen. Once they learn that Chill's actions led to the hated Batman's existence, they turn on their boss and fatally shoot him - just before they realize how valuable his knowledge is to them. Before a dying Chill has a chance to reveal Batman's identity, the Dark Knight intervenes and finishes the goons; Chill dies in Batman's arms addressing him by his true name.

In Detective Comics #235, Batman learns that Chill was not a mere robber, but actually a hitman who murdered the Waynes on orders from a Mafia boss named Lew Moxon. Later, Alfred Pennyworth reminisces that Joe Chill is the son of one Alice Chilton, one-time caretaker of young Bruce Wayne

In the 2008 Grant Morrison story, "Joe Chill in Hell" (featured in Batman #673), Chill is reinterpreted as a mid-level crime boss who builds the Land, Sea, Air Transport company from the ground up, likely through illegal means. He blamed his crimes, including murdering the Waynes, on class warfare. In this story, Batman has visited and frightened Chill every night for a month. Chill is living as a shut in, but his guards never see or catch Batman during the visits. On his final visit, Batman gives Chill the gun he used to kill the Waynes. There is one bullet left within it. Chill finally realizes who Batman is, and fears what his fellow gangsters would do to him if they found out. It is implied that he may have committed suicide, however, it is left ambiguous.

In the Burton BATMAN from 1989, Joe Chill, who's name is never said in the movie, is seen in Crime Alley with The Joker, Jack Naiper. Burton did some rewrites to the script and changed it Naiper who would kill the Waynes, just one of many fuck-ups he made to continuity. He also had Alfred lead a reporter into the Batcave and allowed Batman to kill people.

Nolan and Goyer, who wrote BATMAN BEGINS, did it right, leaving Chill as the killer and actually making him a sympathetic character. This version of Chill claims to have been driven to mug the Waynes because of the desperation of the times, as Gotham was undergoing an economic depression because an undisclosed action by the League of Shadows. He is arrested soon after killing Bruce's parents. Years later, he undergoes a hearing to be released from prison as part of a deal to testify against Gotham mob boss Carmine Falcone. During the hearing, he claims to regret his crime. Afterward, despite police presence, he is killed by one of Falcone's assassins.

It is later discovered that Falcone had bribed the judge of Chill's case to make the hearing public and bring Chill out into the open. The young Bruce Wayne, who is waiting outside the courtroom with a gun of his own, is thus deprived of his own chance for revenge. Bruce's lost chance of killing Chill himself helps him realize what justice really is, and his memories of a gun taking his parents' lives brings him to his rule that he will not kill. Bruce later confronts Falcone, who taunts him by saying that Chill bragged that Thomas Wayne "begged like a dog" before his death which was a lie.

 
Joe Chill's actions that night in Crime Alley forever changed Gotham City. The Waynes, who had been working towards saving the city, were murdered by one of the very people they were trying to help. Chill went on to be a player in the Gotham crime scene, and though not a major one, as Bane proved, one event can be enough to cement a legacy in Gotham.

Detective Comics #66 (August 1942)

When he first appears in Detective Comics #66, the character's name is Harvey Kent. His name is later changed to Harvey Dent to prevent confusion with Clark Kent. However, the original name is made reference to in the "Prodigal" storyline, where Harvey Dent walks due to a clerical error which causes him to be confused with a similarly named Harvey Kent. At 26, he is the youngest district attorney ever to serve Gotham City, and is nicknamed "Apollo" for his good looks. He is elected about six months before Batman begins his war on crime, as depicted in the events of Batman: Year One.

His campaign against crime ends tragically during the prosecution of crime boss Sal Maroni for murder. At a climactic moment in the trial, Harvey produces Maroni's good luck charm, a two-headed coin, which had been found at the murder scene with Maroni's fresh fingerprints upon it. Enraged, Maroni throws sulfuric acid in Harvey's face, horribly scarring his left hand and the left half of his face while leaving the other half undamaged; in some versions of the story, Harvey is only saved from a face-full of acid by Batman's quick, but only partial, deflection of Maroni's hand. Driven insane by his hideous reflection, Harvey scars one side of Maroni's coin and lets tosses of the coin decide whether he acts for good or evil in any situation.

 
In the wake of Frank Miller's 1987 revision of Batman's origin, Andrew Helfer rewrote Two-Face's history to match. This origin, presented in Batman Annual #14 (above), served to emphasize Dent's status as a tragic character, with a back story that included an abusive, alcoholic father, and early struggles with bipolar disorder and paranoia. It was also established, in Batman: Year One, that pre-accident Harvey was a major heroic figure working as one of Batman's earliest allies. Harvey had clear ties to both Batman and Commissioner Gordon, making him an unsettling and personal foe for both men. Mafia chieftain Sal "The Boss" Maroni is still the criminal who disfigures Harvey with help from the corrupt A.D.A. Adrian Fields. Fields provides Maroni with the acid, concealed in an antacid bottle. Two-Face gets his trademark coin from his abusive father, who would employ the coin in a perverse nightly "game" that would always end with Harvey being beaten. This would instill in Harvey his lifelong struggle with free will and his eventual inability to make choices on his own.

  
After Maroni's trial, Dent escapes from the hospital and confronts Fields, who tries to bargain with Dent by offering a massive file of criminal funds, hideouts, and connections for his old boss to begin his "new life." When Batman interrupts them, Two-Face kills Fields and then, losing the coin toss, confronts his father and forces him to play the game they used to play. The coin comes up clean, so he spares his father, and is incarcerated in Arkham Asylum While there he receives an experimental plastic surgery, but in a fit of madness, he claws his face open with his bare hands.

In The Long Halloween, Harvey escapes from the hospital and hides out in the sewers for weeks, finally resurfacing as Two-Face to take revenge on the mob, killing Fields and mob boss Carmine Falcone, as Maroni has already been assassinated by this point by Falcone's son Alberto.

Two-Face only made three appearances in the 1940s, and appeared just twice in the 1950s. By this time, he was dropped in favor of more "kid friendly" villains. He did appear in 1968 in World's Finest #173 (above) in which Batman declared him to be the criminal he most fears. In 1971, writer Dennis O'Neil brought Two-Face back, and it was then that he became one of Batman's archenemies.

Two-Face is revealed to have murdered the father of the 2nd Robin Jason Todd, who had been one of his henchmen. Todd later has Two-Face at his mercy and chooses not to kill him, embracing Batman's ideal of justice.

In Arkham Asylum: A Serious House on Serious Earth, writer Grant Morrison portrays Harvey's dependence on his coin. The doctors in the asylum attempt to wean him off his evil personality by taking away his coin and replacing it with a die and eventually a tarot deck, effectively giving him 78 options. The treatment fails, however, with so many options, Harvey can't even make simple decisions. At the end of the graphic novel, Batman gives Harvey his coin back, telling him to use it to decide whether to kill him. He tells Batman that the coin landed scar face down, and Batman leaves safely, but the next scene shows the scar face up, meaning that he inexplicably chose to let Batman live. In the hardcover edition, Morrison said this was because it was April Fool's Day.

During the One Year Later storyline, we find out that in Batman's year long absence from Gotham, he left the city in the hands of a rehibilitated and healed Harvey Dent. Harvey patrols the city for a year keeping it safe until Batman's return. At which point he feels unappreciated and rescars his own face taking on the Two-Face persona once again.

Two-Face also has a bit of a rivalry with The Joker, as broke into his house during The Long Halloween and beat him prior to the scarring that made him who his is now. This is also shown in THE DARK KNIGHT, where the Joker is responsible for killing Harvey's girlfriend and scarring his face.

In the other movies, Billy Dee Williams played Harvey Dent in  BATMAN and Tommy Lee Jones butchered the role of a transformed Two-Face in BATMAN FOREVER.

Dent however was just MADE by Arron Eckhart in THE DARK KNIGHT.

 He is also one of the main villains in the new LEGO BATMAN game and was one of the best villains on the Animated Series, where he was voiced by "Bull" from NIGHT COURT.

Harvey has become one of Batman's greatest foes, and an actual foil of himself. So many times Two-Face has almost killed Batman only to have Harvey intervene. He is so interesting because he really represents 3 characters at once. The first, and most prominent would be Two-Face, the 2nd being Harvey, and the 3rd? The coin. Over the years Harvey's coin has become as much of a character as the Batcave or Gotham City itself.

1.

Batman #1 (Spring 1940)

The archenemy of Batman, the Joker is portrayed as a master criminal whose characterization has varied from a violent sociopath who kills people and commits crimes for his own amusement, to a goofy trickster-thief. He has also been directly responsible for numerous tragedies in Batman's life; including, but not limited to, the paralysis of Barbara Gordon and the death of Jason Todd.

 
Above is where he beat the 2nd Robin Jason Todd with a crowbar, before blowing him up. And then we see Joker cripple Barbra Gordon, not even aware that she was Batgirl, as he is looking to kidnap James Gordon. 

The Joker's real identity is unknown. Throughout the character's long history, there have been several different origin tales; the most common theme depicts him as falling into a vat of chemical waste, which bleaches his skin and turns his hair green and his lips bright red, giving him the appearance of a clown.

In his initial dozen or so appearances, starting with Batman #1 in 1940, the Joker was a straightforward mass murderer, with a bizarre appearance modeled after the symbol of the Joker known from playing cards. He was slated to be killed in his second appearance, but editor Whitney Ellsworth suggested that the character be spared. A hastily drawn panel, demonstrating that the Joker was still alive, was subsequently added to the comic. For the next several appearances, the Joker often escaped capture but suffered an apparent death by (falling off a cliff, being caught in a burning building, etc.), from which his body was not recovered.

In the 1950s and 1960s, following the imposition of the Comics Code Authority censorship board, the Joker shifted toward becoming a harmless, cackling nuisance. He disappeared from Batman stories almost entirely when Julius Schwartz took over editorship of the Batman comics in 1964.

In 1973, the character was revived and profoundly revised in Batman stories by writer Dennis O'Neil and artist Neal Adams. Beginning in Batman #251, with "The Joker's Five Way Revenge", the Joker returns to his roots as a homicidal maniac who murders people on a whim, while enjoying battles of wits with Batman.

O'Neil said his idea was "simply to take it back to where it started. I went to the DC library and read some of the early stories. I tried to get a sense of what Kane and Finger were after." Steve Englehart and Marshall Rogers, in an acclaimed run in Detective Comics #471-476, which went on to influence the 1989 movie BATMAN and be adapted for the 1990s animated series, added elements deepening the severity of the Joker's insanity.

In the story "The Laughing Fish", the Joker is brazen enough to disfigure fish with a rictus grin, then expects to be granted a federal trademark on them, only to start killing bureaucrats who try to explain that obtaining such a claim on a natural resource is a legal impossibility.

 
The Joker had his own 9-issue series during the 1970s in which he faces off against a variety of both superheroes and supervillains. Although he was the protagonist of the series, certain issues feature just as much murder as those in which he was the antagonist; of the nine issues, he commits murder in seven. The development of the Joker as a sociopath continues with the issues A Death in the Family and The Killing Joke in 1988, redefining the character for DC's Modern Age after the company wide reboot following Crisis on Infinite Earths.

 
A definitive back-story has never been established for the Joker, and his real name has never been confirmed. He has been portrayed as lying so often about his former life that he himself is confused as to what actually happened. As he says in The Killing Joke: "Sometimes I remember it one way, sometimes another... if I'm going to have a past, I prefer it to be multiple choice!" In Arkham Asylum: A Serious House on Serious Earth written by Grant Morrison, it is said that the Joker may not be insane, but has some sort of "super-sanity" in which he recreates himself each day to cope with the chaotic flow of modern urban life. On several occasions the Joker has been know to address the reader in the comics, implying that he has another level of awareness beyond the pages of the comic book and may even know he is fictional.

The most widely cited backstory, which the official DC Comics publication, Who's Who in the DC Universe, credits as the most widely believed account, can be seen in The Killing Joke. It depicts him as originally being an engineer at a chemical plant who quits his job to become a stand-up comedian, only to fail miserably. Desperate to support his pregnant wife, Jeannie, the man agrees to help two criminals break into the plant where he was formerly employed. In this version of the story, the Red Hood persona is given to the inside man of every job (thus it is never the same man twice); this makes the man appear to be the ringleader, allowing the two criminals to escape. During the planning, police contact him and inform him that his wife and unborn child have died in a household accident.

Stricken with grief, he attempts to back out of the plan, but the criminals strongarm him into keeping his promise. As soon as they enter the plant, however, they are immediately caught by security and a shootout ensues, in which the two criminals are killed. As the engineer tries to escape, he is confronted by Batman, who is investigating the disturbance. Terrified, the engineer leaps over a rail and plummets into a vat of chemicals. When he surfaces in the nearby reservoir, he removes the hood and sees his reflection: bleached chalk-white skin, ruby-red lips, and bright green hair. These events, coupled with his other misfortunes that day, drive the engineer completely insane, resulting in the birth of the Joker.

From the Joker's first appearance in Batman #1, he has committed crimes both whimsical and inhumanly brutal, all with a logic and reasoning that, in Batman's words, "make sense to him alone."

In the aforementioned The Killing Joke, he shoots Barbara Gordon, rendering her a paraplegic. He then kidnaps Commissioner Gordon and taunts him with enlarged photographs of his wounded daughter being undressed, in an attempt to prove that any normal man can go insane after having "one really bad day." The Joker ridicules him as an example of "the average man," a naïve weakling doomed to insanity. The Joker fails in his attempts to drive Gordon insane, because Batman saves the commissioner. Although traumatized, Gordon retains his sanity and moral code, urging Batman to apprehend the Joker "by the book" in order to "show him that our way works." After a brief struggle, Batman tries one final time to reach the Joker, offering to rehabilitate him. The Joker refuses, but shows his appreciation by sharing a joke with Batman and allowing himself to be taken back to Arkham.

(To read Joker's Joke, click the images below)

The Joker murders Jason Todd, the second Robin, in the story A Death in the Family. Jason discovers that a woman who may be his birth mother is being blackmailed by the Joker. She betrays her son to keep from having her medical supply thefts exposed, leading to Jason's brutal beating by the Joker with a crowbar. The Joker locks Jason and his mother in the warehouse where the assault took place and blows it up just as Batman arrives. Readers could vote on whether they wanted Jason Todd to survive the blast. They voted for him to die, hence Batman finds Jason's lifeless body. Jason's death has haunted Batman ever since and has intensified his obsession with his archenemy.

During the events of the No Man's Land storyline, the Joker murders Sarah Essen Gordon, Commissioner Gordon's second wife, by shooting her in the head as she tries to protect the infants that he has kidnapped. He surrenders to Batman, but continues to taunt Gordon, provoking the Commissioner to shoot him in the kneecap. The Joker laments that he may never walk again, and then collapses with laughter as he "gets the joke" that Gordon has just avenged his daughter's paralysis.

 
In a company-wide crossover, Last Laugh, the Joker believes himself to be dying and plans one last historic crime spree, infecting the inmates of The Slab, a prison for super criminals, with Joker venom to escape. With plans to infect the entire world, he sets the superpowered inmates loose to cause mass chaos in their 'Jokerized' forms. Meanwhile, he tries to ensure his "legacy" by defacing statues in his image. The entire United States declares war on the Joker under the orders of President Lex Luthor; in response, Joker sends his minions to kill the President. Black Canary discovers that Joker's doctor modified his CAT scan to make it appear that he had a fatal tumor in an attempt to subdue him with the threat of death. Harley Quinn, angry at the Joker's attempt to get her pregnant without marrying her, helps the heroes create an antidote to the Joker poison and return the super villains to their normal state. Believing Robin had been eaten by Killer Croc, Nightwing eventually catches up with the Joker and beats him to death. To keep Nightwing from having blood on his hands, Batman resuscitates the Joker.

In Emperor Joker, a multi-part story throughout the Superman titles, the Joker steals Mister Mxyzptlk's reality-altering power, remaking the entire world into a twisted caricature, with everyone in it stuck in a loop. The conflict focuses on the fate of Batman in this world, with the Joker torturing and killing his adversary every day, only to bring him back to life and do it over and over again. Superman's powerful will allows him to fight off the Joker's influence enough to make contact with the weakened Mxyzptlk, who along with a less-powerful Spectre, encourages Superman to work out the Joker's weakness before reality is destroyed by the Joker's misuse of Mxyzptlk's power. As time runs out, Superman realizes that the Joker still cannot erase Batman from existence, as the Joker totally defines himself by his opposition to the Dark Knight; if the Joker can't even erase one man, how can he destroy the universe? The Joker's control shattered, Mxyzptlk and the Spectre manage to reconstruct reality from the moment the Joker disrupted everything.

At the conclusion of Infinite Crisis, the Joker kills Alexander Luthor, hero of the original Crisis on Infinite Earths and villain of Infinite Crisis for being left out of the Society.

The Joker is a main character in the Salvation Run miniseries, leading one of two factions of supervillains who have been exiled from Earth to a distant prison planet. In issue six of the series, Joker engages Lex Luthor in an all-out brawl. Just as he gains the upper hand, however, the planet is invaded by Parademons, he helps fight off the invasion and later escapes along with the rest of the surviving villains in a teleportation machine.

  
Joker, the most prominent villain in the entire DC Universe even go the honor of bludgeoning Lois Lane to death in Kingdom Come, taking away what should have been Lex Luthor's right.

Wizard Magazine's list of the 100 Greatest Villains of All Time ranked the Joker as #1.

Even other villains seem to be afraid to work with the Joker, especially those based in Gotham who have spent time with him at Arkham.

Joker is the most used violin in all of comics and has done everything. He is featured in pretty much every Batman video game and all the cartoons.

The Joker has appeared in numerous Batman-related media, including portrayals by Cesar Romero, Jack Nicholson, and Heath Ledger, and animated versions with voice actors Mark Hamill and Kevin Michael Richardson.

As good as Nicholson was in BATMAN, Ledger was PER-FECT. THE DARK KNIGHT was the best movie of 2008 and I couldn't have been happier with his performance.

The Joker is Batman's foil. He is chaos and mayhem against Batman's order and justice. He kills for fun and seems to be in on a joke no one else gets. However, his greatest weakness is his inability to survive without his nemesis. In Going Sane, Upon thinking Batman was dead, Joker completely reforms. Also, Joker has saved Batman's life maybe more times than Robin. Anytime another villain has a real chance to end the Dark Knight, Joker makes sure they know that only he has the right to kill the Batman. He originally killed Mr. Freeze and has come close to killing Harley Quinn, Black Mask, and Two-Face all for just that reason.

The Joker is my favorite character of all time. He wins.

It is these villains that make me love Batman. A hero is only as good as his advasaries, and Batman's are that best.

 Alright Gang. That's what I got. Thanks for taking the time to look at it. (This font is called "Batang")