Jack Nicholson's 50 Major Roles Ranked, From 'The Shining' to 'Anger Management' (Photos)

TheWrap weighs in on 50 parts played by Oscar winner

Jack Nicholson is a legend. Period. His illustrious career has been spent playing brooding rebels, crazed villains and sneering charmers on the big screen. Soon he’ll star opposite Kristen Wiig in a remake of “Toni Erdmann.” The three-time Oscar winner is undoubtedly a fixture of American cinema (as well as courtside at the Lakers). In honor of Nicholson’s 80th birthday (on Saturday, April 22), we’ve done the near impossible: ranked all of his major, iconic roles, from great to best.

50. “Man Trouble” (1992)“Man Trouble” is a ridiculous screwball crime comedy in which Nicholson and Ellen Barkin get upstaged by horny dogs. 

49. “Blood and Wine” (1996)  Despite re-teaming with “Five Easy Pieces” director Bob Rafelson and having Michael Caine as his co-star, even Nicholson couldn’t save this generic heist thriller.

48. “A Safe Place” (1971)  This bizarre, formless ‘70s relic that is based on a play stars Tuesday Weld and Orson Welles opposite Nicholson about a girl living a fantasy in which she never grows up.

47. “The Terror” (1963)  Nicholson gives a stiff performance in this Roger Corman picture opposite Boris Karloff. The upshot: He gets to kiss a woman who transforms into a corpse.

46. “The Bucket List” (2007)  While brilliant, Nicholson and Morgan Freeman are a bit saccharine in this cornball comedy about two cancer patients trying to live out their dying wishes.

45. “How Do You Know” (2010)   Nicholson’s role as a business tycoon in this romantic comedy marks one of his many collaborations with James L. Brooks.

44. “The Cry-Baby Killer” (1958)  Nicholson’s first ever movie was a sensationalized B-movie about how new music is making kids run wild on killing sprees.

43. “On a Clear Day You Can See Forever” (1970)   Nicholson has only a minor role in this lavish, fantastical film from Vincente Minnelli, and starring Barbra Streisand. He looks wildly out of place. Fun fact: A sweet duet he performed with Streisand was ultimately cut from the final film.

42. “Anger Management” (2003)  Adam Sandler plays the rare straight man to a comedic performance by Nicholson that includes a lot of shouting, grinning and even a bit of singing.

41. “The Two Jakes” (1990)  Nicholson directed himself in this sequel (that no one asked for) to “Chinatown,” where he reprised his role as J.J. Gittes.

40. “Hoffa” (1992)  Not only is Danny DeVito’s “Hoffa” essentially fiction, Nicholson’s portrayal of Jimmy Hoffa is loud, cold-blooded and foul-mouthed (it is a David Mamet script) with an unnecessarily thick accent.

39. “The Shooting” (1966)  Nicholson made two existential Westerns in 1966. In this made-for-TV film, he’s a quick-draw hired gun helping a woman with a revenge scheme.

38. “Ride In The Whirlwind” (1966)  Like “The Shooting,” “Ride in the Whirlwind” is an unusual, bitter and morally ambiguous Western, and Nicholson’s still clearly green.

37. “The Fortune” (1975)  We don’t often get to see Nicholson playing a bumbling dimwit, so that’s one reason to watch him play off Warren Beatty in Mike Nichols’ farce, which some consider a cult classic.

36. “Flight to Fury” (1964)  Nicholson co-wrote the screenplay for this adventure film shot in the Philippines. His meaty villain role was enough to get him noticed.

35. “Hells Angels On Wheels” (1967)  Nicholson was a star ready to pop in his last B-film before “Easy Rider.” He snaps at a customer and fully embodies the rebellious spirit he carried throughout the 1970s.

34. “Tommy” (1975)  Nicholson plays “The Specialist” in The Who’s rock opera, singing “Go to the Mirror” and shooting seductive glances at Tommy’s mom.

33. “Wolf” (1994)  Mike Nichols and Nicholson take the idea of a man turning into a werewolf quite seriously. While Nicholson gives a fairly carnal performance filled with snarling, it’s not all ridiculous.

32. “Mars Attacks!” (1996)  If you love or hate Tim Burton’s campy cult film, part of its charm is Nicholson bellowing “shut up!” at his general and pleading with the new alien overlords.

31. “The Postman Always Rings Twice” (1981)  Nicholson goes hard-boiled in this steamy remake of a classic noir novel and film. He has a torrid love affair with Jessica Lange.

30. “The Last Tycoon” (1976)  Nicholson squares off against De Niro in a tense take on F. Scott Fitzgerald as directed by Elia Kazan.

29. “Goin’ South” (1978)  Nicholson directed this Western-comedy in which he gets hitched as a way of escaping the gallows. And he plays opposite the first film roles of John Belushi and Mary Steenburgen.

28. “The Wild Ride” (1960)  Nicholson does a great James Dean impression as the lead in this black and white, low budget B-movie — just his second film. He plays a slick, laid back, too-cool-for-school street racer who lets his ego get the better of him.

27. “The Crossing Guard” (1995)  This Nicholson performance gets histrionic and melodramatic early as he raves to his wife (Angelica Huston) that he’ll seek vengeance on a drunk driver who killed his daughter.

26. “Something’s Gotta Give” (2003)  Nancy Meyers and Diane Keaton collectively bring out Nicholson’s awkward charm as an aging playboy learning to fall in love with someone his own age.

25. “The Little Shop of Horrors” (1960)   Nicholson’s brief appearance as a pain-obsessed dental patient finds him at his most giddy, and it’s a highlight of this cult horror classic before Bill Murray took a stab at the character.

24. “The Missouri Breaks” (1976)  It’s odd that a movie where Nicholson stars opposite arguably an even greater screen legend in Marlon Brando isn’t more widely remembered. Arthur Penn’s Western is engrossing, thanks to its two eccentric, unusual leads.

23. “The Witches of Eastwick” (1987)  Director George Miller molded Nicholson into his most lascivious, crude and manipulative version of himself for this peculiar blend of fantasy and comedy, successfully seducing Susan Sarandon, Michelle Pfeiffer and Cher.

22. “Broadcast News” (1987)  While his cameo was essentially just a favor to James L. Brooks, Nicholson has a scene-stealing moment as a TV anchor threatening layoffs.

21. “Reds” (1981)  Nicholson and Diane Keaton are sharp, intellectual equals with a strong romantic chemistry in Warren Beatty’s epic about an American journalist in Communist Russia.

20. “Ironweed” (1987)  Meryl Streep and Nicholson star in this weepy, Oscar-bait period piece as two hard-on-their-luck bums in Albany. At times his ragged, old-fashioned look makes him almost unrecognizable.

19. “The Passenger” (1975)  Nicholson goes existential working with Michelangelo Antonioni for this drama of ennui and despair. It’s an underrated project for both star and director.

18. “The Border” (1982)  “The Border” stars Nicholson as a corrupt border patrol agent who likewise has to deal with his own moral divide, a performance that recalls his work in “Chinatown.”

17. “Carnal Knowledge” (1971)  Nicholson anchors Mike Nichols’s character study of sexual mores along with Art Garfunkel, Ann-Margret and Candice Bergen, delivering an intense, serious, dramatic performance culminating in one powerful bedroom rant.

16. “The King of Marvin Gardens” (1972)  Bob Rafaelson perhaps was first to cast Nicholson against type as an introverted, bookish, reserved and depressive radio broadcaster trading in tragedy. And he’s still brilliant.

15. “The Pledge” (2001)  In this underrated pairing with director Sean Penn, Nicholson plays a retiring police chief coping as much with his own despair and anxiety while searching for a missing girl.

14. “Prizzi’s Honor” (1985)  For “Prizzi’s Honor,” Nicholson donned a thick Brooklyn accent that netted him an Oscar nod opposite Angelica Huston in John Huston’s mobster satire.

13. “The Last Detail” (1973)  Hal Ashby’s “The Last Detail” is Nicholson at his saltiest. He plays a sailor who is unabashedly breaking rank in order to give a convicted young private some last moments of glory.

12. “As Good As It Gets” (1997)  Nicholson won his third Oscar walking a nuanced, fine line for his portrayal of a misanthropic, unlikable and obsessive compulsive author in James L. Brooks’ rom-com.

11. “About Schmidt” (2002)  Director Alexander Payne brought out Nicholson’s age and vulnerability for this road trip comedy. He has a gut-wrenching moment as he tears up in the film’s closing moments.

10. “Heartburn” (1986)Nora Ephron based this story about a cheating husband on her own marriage to Washington Post reporter Carl Bernstein. Nicholson and Streep have fleeting moments of chemistry, though his character is too delectably unsavory to suggest meaningful romance.

9. “Chinatown” (1974)    Nicholson’s J.J. Gittes is in every scene of Roman Polanski’s esoteric neo-noir, and he exudes as much sleaze and charm even though he’s got a slashed nose through half of it.

8. “A Few Good Men” (1992)  “You can’t handle the truth!” Nicholson’s few scenes in this courtroom drama show him at his most domineering, barking an incredible monologue at Tom Cruise along with one of the most famous movie quotes of all time.

7. “Batman” (1989)  Before Heath Ledger, Nicholson’s Joker was eloquent, surreal, colorful and the perfect foil to Michael Keaton’s Batman.

6. “Easy Rider” (1969)  Nicholson’s brief stint in “Easy Rider” was enough to make him a star. His paranoid energy as he chugs whiskey and lays truth-bombs about freedom is captivating.

5. “The Departed” (2006)  It’s amazing Nicholson didn’t work with Scorsese sooner. His coked-out Frank Costello is over-the-top menacing in the best possible way. Also Read: 18 Things You Didn’t Know About ‘The Departed’ for Its 10th Anniversary (Photos)

4. “Terms of Endearment” (1983)  Nicholson manages to romance Shirley MacLaine even while shooting off some of his best, most insulting and hilarious barbs. “I’d rather stick needles in my eyes!” And — oh yeah — he won an Oscar for the role in the Best Supporting Actor category.

3. “Five Easy Pieces” (1970)  Nicholson’s best anti-hero role finds him trying to escape his silver-spoon upbringing and coming up lost. Watch it for his scathing, sarcastic takedown of an uptight waitress.

2. “The Shining” (1980)  “The Shining” is Jack at peak crazy, bug-eyed, limping and unpredictably erratic. His leering grin as he says “Here’s Johnny” is an indelible image of pure madness.

1. “One Flew Over the Cuckoo’s Nest” (1975)  Nicholson rolled his rebellious spirit into this sobering look at mental illness for the role that won him his first Oscar.
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