His performance focused more on humor than malice, making him a memorable part of pop culture history. #2 Jack Nicholson's charismatic criminal Jack Nicholson's portrayal in Tim Burton's 1989 Batman brought a more charismatic and menacing version of the Joker. #3 Heath Ledger's chaotic mastermind Heath Ledger's Oscar-winning performance in The Dark Knight (2008) redefined the Joker as a chaotic mastermind. Ledger's portrayal delved into themes of anarchy and morality, presenting a darker and more complex version of the character. This version focused on mental health issues and societal neglect, offering a more humanized yet tragic portrayal of the character's descent into madness.