Batman has one of the largest, most diverse and recognizable rogues gallery of all superheroes. The more famous of these include The Joker, Two-Face, Catwoman, and The Riddler.
This will be biased towards the films and animated series, but for the most part the comics have either reflected or influenced the evolution of these villians.
Since I feel the 1993 animated series portrayed these characters so well, most of the clips included are from that series.
As The Joker already has his own topic page, this will focus more on the other villians and their interpretations in different mediums.
If anyone has a funny flowchart that would be ideal for this page, just e-mail it to me (here on cracked) and i will post it if i like it.
The inconspicuously named Edward Nigma is a master at riddles and puzzles. He is a certifiable genius and often has ingenious schemes, but obsessively leaves clues and riddles that Batman always solves. Not a psychopath, and most of his crimes are non-violent.
1966 (aka "Adam West"): Spandex wearing, over-the-top giggler who left some of the most absurd riddles you will have ever seen.
1993 (aka "B: TAS"): Loses the tights, gains awesome. Sophisticated intellectual who is a mental match for Batman, and yet struggles with his own insanity. His first appearence is in the embedded video below: for my favorite riddler moment, copy and paste the following URL: http://www.youtube.com/watch?v=EahLltPdk-k
1995 (aka "Schmucker"): acts exactly like Ace Ventura, just with more spandex and crotch adjusting.
Since: Turns emo for the newer animated series "The Batman", but remains mostly loyal to his 1993 portrayal. Might actually be the most interesting and intriguing villian on the show, is voiced by Robert Englund of "Nightmare On Elm Street" fame, and is literally the ONLY character who doesn't know 8th-Degree level kung-fu (more on this later).
Harvey Dent was Gotham's district attorney and Bruce Wayne's best friend. After a criminal he was prosecuting splashes his face with acid, his previously handsome face is horribly scarred, as seen in the above picture. His personality split into two opposing halves, and became obsessed with chance, never making a decision without flipping his lucky coin. This has led him to even save Batman's life on one occasion. Two-Face is very likely the most tragic of Batman's villians, as he has many times recovered his sanity and had plastic surgery to repair his face (and somehow always get his old job back), only to revert back to insanity.
Pre-1993: See above
1993: Originally thought to be too gruesome to put on TV, "B: TAS" decided to kick conventions in the balls and put him on anyway. On the show, he is simultaneously Bruce's friend and Batman's enemy and one of its more intruiging recurring villians.
1995: The incredibly miscast Tommy Lee jones prances around like a retard.
2008: The incredibly well cast Aaron Eckhart portrays a very dark and menacing Harvey Dent, and gives a performance comparable to Heath Ledger's.
The short, rotund Oswald Copperpot (having the above moniker) is one of Gotham's most powerful crime lords, and specializes in bird-related capers. Well known for his advanced umbrella arsenal, which function as guns, helicopters, buzzsaws, and even as actual umbrellas. He is taken seriously for one reason only (see Post-1993).
1966: Francis Burgess Meredith's Penguin abounds in over-the-top penguin and umbrella related schemes. Coughs like a Penguin (I assume), and almost every interpretation of the character has imitated this one.
1992: Tim Burton turns the Penguin (Danny Devito, beacuse Depp wasn't available) into a sewer-dwelling circus freak with actual bird-like deformities and an umbrella switch-blade. To everyone's surprise, this actually works, and Devito gives a solid performance as a villian that both disgusts us and gains our pity.
1993: The Penguin retains the unpredictable, psychotic nature of Devito's Penguin and the sophisticated nature of Meredith's Penguin, becoming a mixture comparable to Peanut Butter and Chocolate.
Post-1993: In "The Batman", The Penguin talks like the Meredith Penguin, has the umbrella switch-blade and physical deformities of the Devito one, but has one major difference- he will SOUL PUNCH YOU WITH HIS KUNG-FU. I swear I am not kidding. If for no other reason, find an episode of that show and watch it.
(Also shows his two strange hench-women)
Selina Kyle has appeared in Batman comics since "Batman #1" appeared in 1940. She has more alternate backstories than lives, so just know that she is a thief with cat-themed tools, costume, and goals. She is also one of Batman's off-on-again love interests.
1966: Played by three actresses (Lee Meriwether, Julie Newmar, and Eartha Kit). They all say "purrrr-fect" a lot.
1992: Becomes "Burtone-ized" into an unstable, psychotic, revenge-bent ball of female aggression who seduces both Bruce Wayne AND Batman. Played by Michelle Pfieffer, presumably because Helena Bonham Carter was not available.
1993: The complex relationship between Catwoman and Batman is emphasized, and she is less psychotic and instead is an obsessive thief.
Post-1993: Absurd rumors circulate that a supposed "Catwoman" film is released starring, of all people, Halle Berry, otherwise known as "The Woman With 2 Talents". Fortunately, true Batman fans rightfully ignore these rumors.
Above: Robin being a valuable contributor to the Bat-team
Pamela Isley is an eco-terrorist dedicated to preserving the environment, albiet through insanely murderous plots. Her backstory and powers vary through the different interpretations, but the constants are that she used to be a botanist who was somehow mutated into becoming a plant woman. Her consistent powers include an ability to manipulate plant growth, often creating monstrous predatory plants, the ability to seduce any man to her will by manipulating her pheremones, and immunity to any toxin.
1993: Poison Ivy is a consistently recurring villian, who sometimes teams up with another villianess, Harley Quin. She remains a villian that doesn't seem to be inherantly evil, but nonetheless insane.
1997: Uma Thurman plays Poison Ivy, and does her best to make the character as retarded as possible (succeeds).
Post-1997: In "The Batman", Poison Ivy's powers are exponentially upgraded to near god-like proportions, even being able to enslave Superman (with the help of kryptonite dust), and cause plants to grow to giant sizes nearly instantaneously. Batman still beats her, and makes it look easy.
Dr. Johnathan Crane is a former psychiatrist who, as his villianous alter ego, exploits the phobias and deep-rooted fears of his enemies by chemical and psychological means. While some of Batman's enemies, such as The Riddler, gradually lost their effectiveness as villians (in the comics) after Batman had beaten them multiple times, The Scarecrow is consistently able to challenge Batman and bring out his deep rooted, subconscious fears. Surprisingly, this villian has hardly changed at all throughout comic history.
1993: The Scarecrow makes multiple appearences as an excellent villian during "B: TAS". However, almost every time he appears he has a different look, as producer Bruce Timm felt the character never looked scary enough. (I'm afraid to find out what he feels is "scary").
(PS: i have no earthly idea what is going on with the above picture)
2004 (Surprise! Actual Comic book content): In a 2004 story arc, the Penguin turns The Scarecrow into a mutated monster called The Scarebeast, making him a physical match for The Dark Knight. And no, i have no freaking clue how he did it.
2005-2008: Cillian Murphy (who was born to play a Batman villian of some sort) portrays The Scarecrow in the films Batman Begins and The Dark Knight, and in my opinion, nails the character. Apparently, the Scarecrow was pretty awesome in the game "Arkham Asylum", as well.
These are the villians that aren't necessarily as famous as the above ones, but definetly deserve mention of some sort.
This is a villian that was completely redefined into awesomeness by "B: TAS". According to the show, Victor Friese was a Cryoscientist who suffered an industrial accident while trying to treat his terminally ill wife Nora. As a result of his accident, Victor has enhanced physical strength, but must wear a special suit to keep his body temperature at the freezing level. He is as cold hearted as his shtick, and using his freeze-gun he commits cold or ice related crimes in an effort to find a cure for his wife.
Prior to 1993: Mr. Freeze is just a dime-a-dozen mad scientist.
1993: "B: TAS" completely redoes his entire motivation and back-story (ie. creates one), making him one of the most sympathetic and popular recurring characters. His debut episode, "Heart of Ice", wins the show an Emmy.
PUT THE COOKIE DOWN!!
1997: Oh, boy. The "Ahnold" version has the same motivation as the "B: TAS" version, but retains none of the cold, emotionless personality. Instead, he (infamously) spends most of the movie making horrible ice-related puns.
Post-1997: In a recent comic book developement, Mr. Freeze gives up hope that his wife will ever be cured and decides to simply kill everybody. In the animated series "The Batman", Mr. Freeze is exactly like he was in "B: TAS", minus the intriguing backstory and reasonable motivation.
He also makes an awesome appearence in one "Batman Beyond" episode.
According to the comics, Ra's Al Ghul is hundreds, if not thousands, of years old. Using a secret bath of chemicals referred to as the "Lazarus Pits", Ra's is able to delay death and recover from normally fatal injuries. Ra's controls a vast terrorist organization called "The Demon" that attempts to restore economic and social balance to the world. Ra's is unique for a villian, in that he is both a physical and mental match for Batman, whom Ra's refers to as "Detective". His daughter, Talia, is one of Batman's love interests, and Ra's has repeatedly tried to have Batman marry her, as he believes that only Batman is a worthy heir to his empire. Ra's is a big-time player who has had conflicts with other DC heroes, and even the entire Justice League.
Hair loss affects everyone- even supervillians.
1993: Ra's makes multiple appearences, and his character is virtually the same as in the comics. In "Batman Beyond", he transfers his soul into the body of his daughter Talia, which suggests more mental disorders that i would like to discuss here.
2005: Liam Neeson stars as a Ra's who gives guidance to a younger Bruce Wayne and teaches him how to manipulate the fears of criminals. However, Batman's oath to never kill brings him into direct conflict with Ra's, who wants to destroy Gotham and restore balance to society.
Bane is one of Batman's more awesome villians, because he regularly beats the tar out our hero.
Bane grew up in a South American prison, serving the life sentence of his father who had died. Within prison, Bane honed his body to stellar proportions and read as many books as he could, thereby also developing his mind. He was chosen to be an experimental subject as part of a project to create a new kind of supersoldier (because apparently governments trust ex-convicts to be the most loyal kind of person to endow with superpowers). The experiment proved to be a success- Bane's already considerable strength was boosted many times over by the steroid Venom. He subsequently escaped, and embarked on a life of crime. A mercenary of sorts, Bane is, much like Ra's, both intelligent and strong enough to beat Batman on occasion.
1993: In a comic storyline, Bane is introduced and doesn't do anything much. Besides, you know, BREAKING BATMAN'S BACK!!!
In this case, the comic book sound effect is spot on.
1993 (B: TAS): Bane makes numerous appearence and has the same abilities as his comic self, but does not have the same intelligence level.
1997: Bane is reduced to a mindless goon with more spider veins than today's Sylvester Stallone. Becomes prime target for the SMURF ("Steroids Make U Retarded Freak" ) Organization.
As you can see, two completely different people.
Post-1997: In The Batman, Bane has a strange red skin color, but besides that he's exactly the same as in the other animated series. He beats The Batman several times early on in the series, but as the show progresses Bane (like the other villians) becomes more pathetic (more on this later).
In my opinion, if Bane makes it into another Batman film, he can only be played by this guy:
Harleen Quinzel was introduced in "B: TAS" as a side character accomplice to the Joker. She quickly became one of the most popular characters on the show, and earned her own spin-off comic book which explained her back story. She was once a psychology intern at Arkham Asylum, and she fell madly in love with the Joker while working there. Eventually, she decided to don a harlequin outfit and become the Joker's female side-kick. While she remains steadfastly loyal to the Joker, the Joker doesn't exactly return her affections. Wait a second: a girl who remains irrationally, even obsessively, loyal to a pale person who could murder her at any second?
1993: Harley is introduced as one of the Joker's goons. She quickly becomes very popular, and her character develops more personality. She frequently teams up with Poison Ivy to carry out crimes.
Post-1993: Harley has since been incorporated into the DC canon.
This is my personal favorite villian. In the comics, there are 5 incarnations of Clayface, but what is now considered to be the ultimate incarnation of the character is the onw that "B: TAS" created, similarly to what the show did to Mr. Freeze. In the show, Clayface was originally an out-of-work actor named Matt Hagen who had his face disfigured in a car accident. Desperate to regain his career, he used an experimental substance that allows a person to mold his face the way he/she wants it. However, the substance proves to be addicting, and when Hagen is exposed to too much of it, he transforms into the horrendous Clayface. Clayface is very strong, can change his form to look like anyone, and can form blades, giant hands and other shapes out of his clay mass. He does have a weakness to water, in which he can't hold his form, and electric shocks, which temporarily disables him.
Notice how helpful Robin is being in the above picture.
Pre-1993: The first comic adaptation is Matt Hagen. The rest are retarded metaphors for STDs and such (you can't believe how much i wish i was kidding).
1993: Clayface is reimagined in a similar way to Mr. Freeze, and "B: TAS" recieves further praise for this. As a result, the comic version of Matt Hagen is similarly reimagined. Is voiced by Ron Pearlman (!) who, as we all know, is known for portraying perfectly normal people on screen.
Post-1993: There are actually 2 versions of Clayface that appear in "The Batman": the first was a police detective named Eathan Bennett who was an ally of Batman. He had his mind portially broken while he was kidnapped by the Joker, and was mutated by the Joker's "Joker Putty" (creative, I know). He has the same abilities as the "B: TAS" version, but has a different appearence and it is unclear what his weaknesses are (besides being emo and no clear goal, purpose or point). After he is cured, an ugly and untalented actor named Basil Karlo becomes mutated into the new Clayface, and bears a stronger resemblence to the "B: TAS" one.
The animated series "The Batman" was produced and animated by the same team that created the Jackie Chan animated show. As such, they had a lot of experience animating martial arts, and depicted a younger Bruce Wayne/Batman as truly the world's best martial artist. However, as a strange side effect, EVERY ONE OF HIS VILLIANS KNOWS MARTIAL ARTS AS WELL. The Joker? Some monkey-style kung-fu. The short, stumpy Penguin? BALLS-BUSTINGLY GREAT KUNG-FU. Clayface? Kung-Fu. Catwoman? Kung-fu.
Even more bizarre is that every villian who does not know martial arts is incredibly more powerful than their other incarnations. Clayface has no weaknesses, Poison Ivy is a practical demi-god, and Mr. Freeze doesn't even need a freeze gun- he just shoots ice out of his hands. Fire Fly is, in essence, a 21st Century Boba Fet, as he has an advanced jet pack and laser weapons.
Even more bizarre than that? "The Batman" anihilates them in hand-to-hand combat EVERY TIME, especially in the later seasons. I'm serious- by season 5, The Batman NEVER loses a fight to these incredibly over-powered villians, even when facing 3 or more that he never would have beaten man-to-man in season 1. Case in point:
That's right: The Batman and Robin just beat his entire rogues gallery in less than two minutes.
I know what you're thinking- this is actually AWESOME, not weird. Well, how about this- what is even STRANGER is that when "The Batman" isn't fighting the major villians, he doesn't waste time on conventional goons like the other pussy Batmen do- during his off time, "The Batman" fights (and i'm dead serious), dozens of ninjas at the same time, hundreds of vampires at the same time, and a troop of acrobatic circus midgets, all with HIS BARE HANDS. Guess who actually manages to beat "The Batman" in their first encounter: