With The Batman 2 officially underway, discussion of what villains the film should introduce has been a hot topic. The character has a historic selection of enjoyable rogues, between standard organized criminals, and the supervillains the world is most known for.
But which villains has Batman been duking it out with the longest? The early days of Batman saw a good amount of trial and error with its characters, and many of the early villains would stand the test of time. Some however, transcended the pages and became part of the greater Batman legend, appearing in movies, TV series, and more.
Two-Face
"You either die a hero or live long enough to see yourself become a villain" was such an iconic quote that it's worked its way into the American lexicon. But Two-Face goes way beyond The Dark Knight, having first appeared all the way back in 1942.
The character has evolved since its early days, exploring a concept of duality inside the body of Harvey Dent. Some adaptations linger on the good side of Harvey Dent, exploring the path to his descent, with The Long Halloween being a prime example.
Sal Maroni
Typically overshadowed by the more recently created Carmine Falcone, Sal Maroni is still has a prevalent criminal organization throughout most of the Batman mythology. The character was initially written in 1942 as the man who would damage Harvey Dent's face, leading to him becoming Two-Face.
Maroni can be seen in multiple organizations warring with Carmine Falcone, creating an interesting dynamic in Gotham City. Their conflict is a central plotline in season one of Gotham and is often used to show the lack of power of the Gotham City Police Department.
The Penguin
Most recently played by Colin Farrell in The Batman, The Penguin will have his own HBO Max show, which is in early development (per Variety). Even with one of the more campy villain names, the character has lasted since December of 1941, when he first made his mark as a painting thief.
The Penguin isn't too dissimilar to where he began, as an economically minded criminal with ties to Gotham's underworld in various transgressions. Having been played by Danny DeVito, Robin Lord Taylor, and also Colin Farrell, the character has had a number of screen adaptations capturing different aspects of his comic persona. The different Penguins can be represented by zodiac signs.
Scarecrow
Originally depicted in 1940 as a disgraced psychologist, fired from his practice due to inhumane experiments, Scarecrow quickly became an evil force in Gotham. Scarecrow is a villain not normally motivated by money like many others, making him one of Batman's more unpredictable villains.
The character was portrayed by Cillian Murphy in The Dark Knight trilogy, as well as Vincent Kartheiser in Titans. The series portrayed Scarecrow in a Hannibal Lector like manner, having him initially help Dick Grayson with solving a crime. The character is extremely intelligent but is often used now to tell more psychological stories for Batman. The idea makes him perfect for Matt Reeves' Batman universe.
Clayface
A character who has changed vastly since his original design is Clayface, whose original run in 1940 depicted him as a failed actor turned murderer. The character had no powers as he would possess in modern comics, but the element of him being an actor at heart has persevered throughout time.
The Silver Age of comics introduced the shape-shifting aspect of Clayface, and later on, the two personas would merge, turning him into a shapeshifting actor. The character has a very popular interpretation in the Harley Quinn animated series and remains one of the most anticipated villains for a live-action adaptation.
Tony Zucco
Commonly associated with the origin story of Dick Grayson, Tony Zucco was introduced in 1940 as the criminal responsible for the death of Grayson's parents. The story has remained consistent all the way to The New 52 and beyond, with Zucco being a central part of Dick Grayson's character arc.
In one of Batman: The Animated Series' most emotional episodes, the two-part Robin's Reckoning summarized Robin's obsession with the character and his growth in overcoming Zucco. The origin of Zucco and his own life aside from Robin has been explored more in-depth in recent years as well.
Catwoman
One of the most popular Batman villains, partially due to the recent portrayal by Zoë Kravitz, Catwoman has been developed since the early Batman comics. The 1940 appearance initially depicted her and Batman's relationship in a similar way to how it is today, with romantic chemistry constantly underlining Catwoman's ruthless and criminal behavior.
Catwoman has been developed since then as a survivor of a poor upbringing, making her a more empathetic character that some consider an antihero. Unlike many Batman villains, Catwoman's behavior is often justifiable in that she steals from those who have hurt her or hurt others.
The Joker
The Clown Prince of Crime is one of Batman and DC's first supervillains, having appeared in 1940 in a manner not dissimilar from his modern-day interpretations. The character has evolved over time, as writers began to examine him from a psychological standpoint, building mythology on the otherwise mysterious upbringing of the character.
Alan Moore's The Killing Joke is considered one of the greatest Joker comics and serves as the inspiration for many of his on-screen and comic adaptations today. The story inspired Todd Philips's 2019 film Joker.
Hugo Strange
Like multiple villains in 1940 when Hugo Strange was introduced, he was a bank robber. Even then he was a character with great intellect, so it was his motivations that would shift over time. Like many villains, his origins were explored in the Post-Crisis canon, developing his character further.
Strange has a fascination with Batman and has succeeded in finding out his secret identity, making him a very threatening adversary. The character is often portrayed as being interested in inhumane scientific experiments, which he uses to obtain power and knowledge, rather than the money he sought in the '40s.
Joe Chill
Like with Tony Zucco for Robin, the cause of Batman's origin has remained consistent from day one. Created shortly after Batman's first appearance in 1939, Chill was brought in as the man who killed Bruce Wayne's parents. Though, his actual name wasn't discovered until years later.
Joe Chill played a prominent role in Batman Begins, as overcoming the desire to kill him and directly avenging his parents, is often a key component of Batman's growth. In recent storylines, Batman has even gone on to forgive Chill for his actions, as he understands they were out of desperation.