Jack Nicholson has had a long career playing brooding rebels, crazed villains and sneering charmers on screen. Soon he’ll star opposite Kristen Wiig in a remake of “Toni Erdmann.” He’s a fixture of American cinema and the Lakers courtside seating. For his 80th birthday, we aimed to rank all of Jack’s major, already iconic roles, from worst to best.
“Man Trouble” (1992)
“Man Trouble” is a ridiculous screwball crime comedy in which Nicholson and Ellen Barkin get upstaged by horny dogs. It seems impossible the same guy who did “Five Easy Pieces” made this.
“A Safe Place” (1971)
This bizarre, formless ’70s relic based on a play stars Tuesday Weld and Orson Welles opposite Nicholson about a girl living a fantasy in which she never grows up.
“The Terror” (1963)
Nicholson gives a stiff performance in this Roger Corman picture opposite Boris Karloff, but he gets to kiss a woman who transforms into a corpse.
“The Bucket List” (2007)
Nicholson and Morgan Freeman are purely saccharine in this cornball comedy about two cancer patients trying to live out their dying wishes.
“How Do You Know” (2010)
Nicholson’s most recent role as a business tycoon and one of many collaborations with James L. Brooks might be the most memorable thing about this rom-com.
Nora Ephron based this story about a cheating husband on her own marriage, but while Nicholson and Streep have fleeting moments of chemistry, his character is too sleazy to suggest meaningful romance.
“Blood and Wine” (1996)
Despite re-teaming with Bob Rafelson and having Michael Caine as his co-star, Nicholson couldn’t save this generic heist thriller.
“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.
“On a Clear Day You Can See Forever” (1970)
Nicholson has only a minor role in this lavish, fantastical film from Vincente Minnelli starring Barbra Streisand, and he looks wildly out of place. His sweet duet with Streisand was ultimately cut from the final film.
“Anger Management” (2003)
Adam Sandler plays the rare straight man to a comedic performance that’s Nicholson without any of the nuance: a lot of shouting, grinning and even a bit of singing.
“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.
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.
“The Shooting” (1966)
Nicholson made two existential Westerns both released on TV in 1966. In this film, he’s a quick-draw hired gun helping a woman with a revenge scheme.
“Ride in the Whirlwind” (1966)
Like “The Shooting,” “Ride in the Whirlwind” is an unusual, bitter and morally ambiguous Western, and Nicholson’s still green.
“Flight to Fury” (1964)
Nicholson co-wrote the screenplay for this adventure film shot in the Philippines, and his meaty villain role was enough to get him noticed.
“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 ’70s.
Nicholson plays “The Specialist” in The Who’s rock opera, singing “Go to the Mirror” and shooting seductive glances at Tommy’s mom.
“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‘s farce, which some consider a cult classic.
Mike Nichols and Nicholson take the idea of a man turning into a werewolf quite seriously. While Nicholson gives a fairly carnal performance full of snarling, it’s not all ridiculous.
“Mars Attacks!” (1996)
If you love or hate Tim Burton’s campy cult film, part of its charm is Nicholson’s bellowing “Shut up” at his general or pleading with the new alien overlords.
“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, but the original holds up better.
“The Last Tycoon” (1976)
Nicholson squares off against De Niro in a tense take on F. Scott Fitzgerald as directed by Elia Kazan, but neither actor gets fully unhinged.
“Goin’ South” (1978)
Nicholson directed this Western-comedy in which he gets hitched as a way of escaping the gallows. But his performance is memorable only because it’s opposite the first film roles of John Belushi and Mary Steenburgen.
“The Crossing Guard” (1995)
This Nicholson performance gets histrionic and melodramatic quick as he raves to his wife (Angelica Huston) that he’ll seek vengeance on a drunk driver who killed his daughter.
“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.
“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 curious thanks to its two eccentric, unusual leads.
“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.
“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.
“The Witches of Eastwick” (1987)
Director George Miller molded Jack 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.
“Broadcast News” (1987)
While his cameo was essentially just a favor to James L. Brooks, Nicholson has a scene-stealing moment as an executive threatening layoffs.
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.
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.
“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.
“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.”
“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.
“The King of Marvin Gardens” (1972)
Bob Rafaelson perhaps was first to cast Nicholson against type, introverted, bookish, reserved and depressive as a radio broadcaster trading in tragedy, but he’s still brilliant.
“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 as finding a missing girl.
“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.
“The Last Detail” (1973)
Hal Ashby’s “The Last Detail” is Nicholson at his saltiest, playing a sailor unabashedly breaking rank in order to give a convicted young private some last moments of glory.
“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‘s rom-com.
“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.
“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!”
Before Heath Ledger, Nicholson’s Joker was eloquent, surreal, colorful and the perfect foil to Michael Keaton’s Batman.
“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.
“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.
“The Departed” (2006)
It’s amazing Jack didn’t work with Scorsese sooner. His coked-out Frank Costello is over the top menacing in the best way.
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 broken nose through half of it.
“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.
“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.
“One Flew Over the Cuckoo’s Nest” (1975)
Nicholson rolled his rebellious spirit as bikers and drifters throughout his career into this sobering look at mental illness for the role that would win him his first Oscar.
Related stories from TheWrap:
Jack Nicholson, Kristen Wiig to Star in ‘Toni Erdmann’ Remake
Jared Leto Shares Meme About His Joker Making Heath Ledger, Jack Nicholson ‘Proud’
Jack Nicholson Leaves Young Fan Hanging at Clippers Game (Video)