Joker (Heath Ledger), The Dark Knight (2008)

Although Jack Nicholson delivered an unforgettable performance as the Joker in the 1989 Batman, Heath Ledger’s Oscar-winning turn as the Clown Prince of Crime barely edges it out. Rather than focusing on the Joker’s darkly humorous side, Ledger hones in on how the character’s obsession with chaos and anarchy contrast with Batman’s mission to restore order and justice throughout Gotham City. The Dark Knight provides the actor and co-star Christian Bale with the perfect platform to explore the eternally antagonistic relationship between the iconic hero and villain. From his introduction during that instantly classic bank heist sequence to his final laugh-filled moments with Batman, Ledger’s Joker brought a fresh take to one of the most overdone comic book villains of all. Jared Leto — who will assume the role for Suicide Squad — certainly has a challenge ahead of him if he hopes to win over audiences in the same way Ledger did.