The 50 Greatest Movie Antiheroes of All Time

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Last month, this site took a look at the entirety of cinematic history and cooked up a ranking of the 50 best villains of all time. In honor of this week’s release of Man of Steel, the natural follow-up would seem to be a list of the best heroes — except, ugh, how boring are heroes? They can’t hold a candle to the villains, the supporting goons, or (especially) the antiheroes. The latter is usually defined as a protagonist with no heroic virtues or qualities, but that definition can get a little blurry; some would consider characters that are treated as heroes but have a few unlikable or unpopular qualities (like Han Solo, Dirty Harry Callahan, or Snake Plissken). But a true antihero is made of darker stuff than that. Here are a few examples — well, 50, to be precise.

50. Lester Burnham

THE FILM: American Beauty PLAYED BY: Kevin Spacey WHY WE REMEMBER HIM: He’s the main character and gets all the voice-over, but let’s not forget — this character’s primary motivation is nailing his teenage daughter’s best friend.

49. Cary

THE FILM: Your Friends and Neighbors PLAYED BY: Jason Patric WHY WE REMEMBER HIM: That sauna monologue.

48. Ronnie

THE FILM: Observe and Report PLAYED BY: Seth Rogen WHY WE REMEMBER HIM: Because the sheer delusion of this clearly unbalanced mall security guard turned what looked like a Paul Blart also-ran into one of the most disturbing studio releases in recent memory.

47. Seth Gecko

THE FILM: From Dusk Till Dawn PLAYED BY: George Clooney WHY WE REMEMBER HIM: The tattoos. The black suit. The taunting way he picks up the count of three from the bully in the bar. And the specificity of his admonishment that the clerk (a young John Hawkes) in the opening sequence “be cool.”

46. Porter

THE FILM: Payback PLAYED BY: Mel Gibson WHY WE REMEMBER HIM: The original posters for Brian Helgeland’s remake of Point Blank warned audiences to “get ready to root for the bad guy,” and they did — though the novelty of seeing Mel Gibson shed his heroic persona has, to put it mildly, abated.

45. Colin Sullivan

THE FILM: The Departed PLAYED BY: Matt Damon WHY WE REMEMBER HIM: Scorsese’s Infernal Affairs remake was all about shades of gray, centering as it did on a cop pretending to be a criminal and a criminal pretending to be a cop. But the latter (played to oily, preppy perfection by Damon) is the far less sympathetic, a morals-free climber who thinks nothing of lying, cheating, and ratting.

44. Roger Swanson

THE FILM: Roger Dodger PLAYED BY: Campbell Scott WHY WE REMEMBER HIM: Because he thinks fast, talks fast, and he almost believes his own bullshit. But mostly because his first instinct when his 16-year-old nephew comes to town is to take the kid out cruising for sex.

43. Mark Zuckerberg

THE FILM: The Social Network PLAYED BY: Jesse Eisenberg WHY WE REMEMBER HIM: And that nephew was played by young Jesse Eisenberg, who in turn played Aaron Sorkin’s fictionalized riff on the creation of Facebook. And Eisenberg played the cold, conniving, antisocial social media creator so convincingly that it’s probably influenced how we’ve see him since.

42. Withnail

THE FILM: Withnail and I PLAYED BY: Richard E. Grant WHY WE REMEMBER HIM: He’s clearly a miserable, arrogant, lying alcoholic cheapskate, but he’ll never own up to any of that — the world is to blame for Withnail’s woes.

41. Tommy Gibbs

THE FILMS: Black Caesar; Hell Up in Harlem PLAYED BY: Fred Williamson WHY WE REMEMBER HIM: Director Larry Cohen gave The Godfather a blaxpoitation bent and a James Brown beat in these early-‘70s efforts, in which football star Williamson plays the tough-talking boss of Harlem who takes on the Italian mafia.

40. Johnny Boy

THE FILM: Mean Streets PLAYED BY: Robert De Niro WHY WE REMEMBER HIM: Few have personified the total fuck-up as well as De Niro did in this 1974 film (his inaugural collaboration with Martin Scorsese). From his first appearance, blowing up a mailbox just for the hell of it, to his halfhearted escape attempt, interrupted by an impromptu boogie to Smokey Robinson’s “Mickey’s Monkey,” Johnny is an irresponsible lout, and couldn’t care less what you think of it.

39. Rupert Pupkin

THE FILM: The King of Comedy PLAYED BY: Robert De Niro WHY WE REMEMBER HIM: De Niro and Scorsese again, this time telling the story of a would-be comedian and talk-show host whose lack of talent is only eclipsed by his hunger for fame and desire for ingratiation. The character is both funny and scary, and De Niro plays both angles equally, from his passive-aggressive waiting-room scenes to his wailing at his mother when she dares interrupt his basement talk shows.

38. Neil McCauley

THE FILM: Heat PLAYED BY: Robert De Niro WHY WE REMEMBER HIM: One more from De Niro (for now), as a cold-blooded career thief who prides himself on his detachment and lack of personal relationships — and barely blinks when the test of that code comes at the film’s climax.

37. D-Fens

THE FILM: Falling Down PLAYED BY: Michael Douglas WHY WE REMEMBER HIM: If we’re being honest here, mostly for the “breakfast” scene.

36. Gordon Gekko

THE FILM: Wall Street PLAYED BY: Michael Douglas WHY WE REMEMBER HIM: “The point is, ladies and gentlmen, that greed, for lack of a better word, is good. Greed is right. Greed works.”

35. Youngblood Priest

THE FILM: Super Fly PLAYED BY: Ron O’Neal WHY WE REMEMBER HIM: Priest was a ghetto drug dealer, the worst of the worst, but his smooth style, and the hyper-charismatic performance of Shakespearean actor O’Neal, make it hard to root against him.

34. Jack Grimaldi

THE FILM: Romeo is Bleeding PLAYED BY: Gary Oldman WHY WE REMEMBER HIM: The first of many dirty cops on the list, Grimaldi will sell out his job and do favors for the mob in order to live comfortably and keep his mistress. He’s got no ethics or morals whatsoever, which is one thing that makes him memorable; the other is that he’s played by Gary Oldman at full tilt.

33. Tom Ripley

THE FILM: The Talented Mr. Ripley PLAYED BY: Matt Damon WHY WE REMEMBER HIM: It’s not hard to sympathize with a guy who just wants to fit in — particularly when he’s played by the ever-likable Mr. Damon. It’s when he starts killing people that he shifts out of the conventional protagonist zone.

32. Henry Hill

THE FILM: GoodFellas PLAYED BY: Ray Liotta WHY WE REMEMBER HIM: It wasn’t just that Hill robbed, beat, lied, and intimidated his way to riches and power as a mob man. It was that he so easily dropped the dime on everybody in that Family — and in the end, only regretted that he had nothing left of himself to sell.

31. Terrence McDonagh

THE FILM: Bad Lieutenant: Port of Call New Orleans PLAYED BY: Nicolas Cage WHY WE REMEMBER HIM: It’s easy to forget that Mr. Cage is occasionally capable of truly inspired acting, since he’s so often slumming it in terrible paycheck action movies. But only an actor of Mr. Cage’s, erm, intensity could have quite pulled off the leading role of the drugged-out, hallucinating, wacko cop in Werner Herzog’s not-really sequel to Abel Ferrara’s 1992 cult favorite. Speaking of which…

30. The Lieutenant

THE FILM: Bad Lieutenant PLAYED BY: Harvey Keitel WHY WE REMEMBER HIM: Truth be told, after you watch this crooked cop’s traffic stop of two underage girls, good luck not remembering him.

29. Eddie Coyle

THE FILM: The Friends of Eddie Coyle PLAYED BY: Robert Mitchum WHY WE REMEMBER HIM: Because he’s a snitch at the end of his road — and because he’s played by Robert Mitchum, who knew a thing or two about playing antiheroes.

28. Mickey and Mallory Knox

THE FILM: Natural Born Killers PLAYED BY: Woody Harrelson and Juliette Lewis WHY WE REMEMBER THEM: The lovers-on-the-run are often painted as tragic heroes or victims of circumstance, but there’s nothing sympathetic about these serial killers: their first act as a couple is murdering her parents, and it’s all downhill from there. But director Oliver Stone presents their story as such a pulsing, flashing, multimedia mosaic that it’s hard not to get swept up in their blood-splattered tale.

27. Tony Camonte

THE FILM: Scarface (1932) PLAYED BY: Paul Muni WHY WE REMEMBER HIM: Muni’s portrayal of a ruthless Chicago gangster who’ll stop at nothing until he reaches the top was seldom equaled and rarely surpassed…

26. Tony Montana

THE FILM: Scarface (1983) PLAYED BY: Al Pacino WHY WE REMEMBER HIM: …until Al Pacino took did his Cuban-ized riff on the role in Brian De Palma’s 1983, Miami-set remake. Pacino’s coke-hoovering, machine-gun wielding kingpin reset the table for over-the-top movie mobsters; it also influenced an entire generation of would-be hip-hop kingpins.

25. Cody Jarrett

THE FILM: White Heat PLAYED BY: James Cagney WHY WE REMEMBER HIM: “Made it, Ma! Top of the world!”

24. Robert Ford

THE FILM: The Assassination of Jesse James by the Coward Robert Ford PLAYED BY: Casey Affleck WHY WE REMEMBER HIM: The younger Affleck gave the role of Ford an almost Rupert Pupkin-like social awkwardness, ever-so-subtly shifting the viewer’s allegiance from his character to that of the brutal killer he murdered.

23. Ricky Roma

THE FILM: Glengarry Glen Ross PLAYED BY: Al Pacino WHY WE REMEMBER HIM: The hotshot salesman seems the hero of James Foley’s adaptation of David Mamet’s play — he looks good, he talks good, and he’s played by Al Pacino at his slickest. But he’s a terrible human being, preying on the weak and patronizing his co-workers, though it speaks volumes for Pacino’s charisma that we’re actually rooting for him, in the film’s third act, to get away with swindling a feeble-willed mark of a client (Jonathan Pryce).

22. Jack Carter

THE FILM: Get Carter PLAYED BY: Michael Caine WHY WE REMEMBER HIM: Because it’s Michael Caine packing a shotgun.

21. Johnny Strabler

THE FILM: The Wild One PLAYED BY: Marlon Brando WHY WE REMEMBER HIM: For his immortal response to the question of what he’s rebelling against: “Whaddaya got?”

20. The Driver

THE FILM: Drive PLAYED BY: Ryan Gosling WHY WE REMEMBER HIM: The most unfortunate elevator ride since Damien: The Omen II.

19. Rico

THE FILM: Little Caesar PLAYED BY: Edward G. Robinson WHY WE REMEMBER HIM: Because he was the first and one of the best of the classic gangster movie antiheroes — and because Robinson’s distinctive speaking style and resemblance to Al Capone made this, in the minds of many, the prototypical movie gangster.

18. Catwoman

THE FILM: Batman Returns PLAYED BY: Michelle Pfeiffer WHY WE REMEMBER HER: An unfortunately rare female antihero, Pfeiffer’s Selina Kyle/Catwoman sports a complex duality that makes her, frankly, more interesting than the film’s leading character. (The catsuit doesn’t hurt either.)

17. Tom Powers

THE FILM: The Public Enemy PLAYED BY: James Cagney WHY WE REMEMBER HIM: Let’s not fool around with a bunch of highfalutin’ talk about his embodiment of the gangster movie ethos or any of that — truth be told, it’s the grapefruit in the face.

16. William Munny

THE FILM: Unforgiven PLAYED BY: Clint Eastwood WHY WE REMEMBER HIM: Over the ‘70s and ‘80s, Eastwood’s Westerns became increasingly nuanced in their considerations of the psychological ramifications and effects of frontier violence. That came to a climax with this, his final oater (to date), in which Munny — now retired, once a cold-blooded murderer of women and children — returns to contract killing, with brutal results. It may be his single greatest talent, but that doesn’t mean it sits any more comfortably in his soul.

15. Walker

THE FILM: Point Blank PLAYED BY: Lee Marvin WHY WE REMEMBER HIM: For that long, loud walk down that long, bare hallway.

14. Mavis Gary

THE FILM: Young Adult PLAYED BY: Charlize Theron WHY WE REMEMBER HER: For bucking the squeamish conventions of the current cinema and flat refusing to change a single thing about her selfish, bitter, sad little life.

13. Charles Foster Kane

THE FILM: Citizen Kane PLAYED BY: Orson Welles WHY WE REMEMBER HIM: Few things are as sad as a potentially great man rendered impotent by his own jealousy, pettiness, unfaithfulness, and resentment.

12. Sonny Wortzik

THE FILM: Dog Day Afternoon PLAYED BY: Al Pacino WHY WE REMEMBER HIM: A bank robber and hostage taker would normally go right into the villain column — but when he’s trying to scratch together cash for his lover’s sex-change operation, the story gets a bit more interesting.

11. Jules Winnfield

THE FILM: Pulp Fiction PLAYED BY: Samuel L. Jackson WHY WE REMEMBER HIM: For the most terrifying breakfast meeting of all time — and its immediate follow-up, an on-the-spot religious conversion.

10. Jake LaMotta

THE FILM: Raging Bull PLAYED BY: Robert De Niro WHY WE REMEMBER HIM: For both the blows he delivers and the hits he receives — from his opponents in the ring, and himself outside of it.

9. Tyler Durden

THE FILM: Fight Club PLAYED BY: Brad Pitt WHY WE REMEMBER HIM: For being the American White Male Id brought to jumpy, edgy life — or, as it turns out, maybe not quite “brought to life” after all.

8. Bonnie Parker and Clyde Barrow

THE FILM: Bonnie and Clyde PLAYED BY: Faye Dunaway and Warren Beatty WHY WE REMEMBER THEM: Arthur Penn’s 1967 masterpiece heralded a new era of antiheroes, figures that embodied the current anti-authoritarian spirit, freed by the newly liberated ratings system to buck sympathy and social mores. Few did so as memorably as Dunaway and Beatty, whose astonishing good looks and considerable charisma almost made us forget that, as the posters memorably noted, “they kill people.”

7. Fred C. Dobbs

THE FILM: The Treasure of the Sierra Madre PLAYED BY: Humphrey Bogart WHY WE REMEMBER HIM: Bogart was still best known for playing heroes when he re-teamed with Maltese Falcon director John Huston for this story of prospectors who go up to the mountains, go a little crazy, and get a little greedy. Bogart’s grizzled, sweaty, paranoid turn remains one of his most skillful.

6. Daniel Plainview

THE FILM: There Will Be Blood PLAYED BY: Daniel Day Lewis WHY WE REMEMBER HIM: The joy with which he explains, carefully, slowly, and precisely, exactly how he has, in fact, drank your milkshake.

5. The Man With No Name

THE FILMS: A Fistful of Dollars; For a Few Dollars More; The Good, The Bad, and the Ugly PLAYED BY: Clint Eastwood WHY WE REMEMBER HIM: The moniker is a bit of a misnomer — Eastwood’s characters in Sergio Leone’s trilogy of “Spaghetti Westerns” did, in fact, have names (or nicknames, at least). But they shared a common spirit, and an interest in splintering the mythology of Hollywood Westerns — up to and including the honorable hero, here re-imagined by Eastwood as a man who will break rules and play dirty, only bound by his own code of survival.

4. Ethan Edwards

THE FILM: The Searchers PLAYED BY: John Wayne WHY WE REMEMBER HIM: Wayne was best known for playing white-hatted heroes, entertaining to watch but not exactly known for their complexity. That wasn’t the case with what may be his finest performance; as Civil War veteran Edwards, who spends years searching for his abducted niece only to turn on her when he feels her purity has been sullied, Wayne created a character who was troublesomely disturbed, and whose racism was implicitly questioned (rather than politely assumed) by the film it inhabited.

3. Patrick Bateman

THE FILM: American Psycho PLAYED BY: Christian Bale WHY WE REMEMBER HIM: The suits, the facial peels, the business cards, that blank expression of smug self-satisfaction. Oh, and Huey Lewis and the News. He sure did love Huey Lewis and the News.

2. Travis Bickle

THE FILM: Taxi Driver PLAYED BY: Robert De Niro WHY WE REMEMBER HIM: Few films in all of American cinema put us into the uncomfortable skin and disturbed mind of a truly troubled individual with the power and fearlessness of Martin Scorsese’s 1976 masterpiece. Robert De Niro’s iconic performance as Travis Bickle has been boiled down, over the past 30-plus years, into a series of images and catchphrases, most frequently his improvised “You talkin’ to me?” speech. What’s less quoted is the line that follows, and holds the key to the entire unsettling character: “Well I’m the only one here.”

1. Michael Corleone

THE FILMS: The Godfather; The Godfather Part II PLAYED BY: Al Pacino WHY WE REMEMBER HIM: The fall of Michael Corleone is less like that of a typical American film and more like Greek tragedy: the favorite son, done in not just by a blood lust for revenge, but his discovery that he is good at evil. That skill eventually overtakes his life and what is left of his soul, however, as his cold-blooded disengagement from his brother Fredo and his wife Kay result in a character who is, by the end of the second film, a heartless monster, all alone, the antihero transformed into villain.