20. Reds (1981)
Despite being a colossal platform for Warren Beatty as its director-star – perhaps the high point of his Hollywood prestige – this epic about John Reed and the October Revolution featured Jack Nicholson on scene-stealing, smouldering form as the dramatist Eugene O’Neill, who was painfully in love with Reed’s lover and then wife Louise Bryant, played by Diane Keaton.
19. The Witches of Eastwick (1987)
Nicholson was deep into his grinning-devil mode for this movie, based on the John Updike novel – a mode to which he brought charisma and force, but not much depth. He is the satanically alluring bachelor Darryl Van Horne, who moves into a small New England community and forms a connection with three women who don’t realise they are witches, played by Cher, Michelle Pfeiffer and Susan Sarandon.
18. Prizzi’s Honor (1985)
John Huston’s hitman-hitwoman black comedy caper, anticipating the Mr & Mrs Smith shenanigans of Brad Pitt and Angelina Jolie 20 years later, was considered a brilliantly irreverent satirical take on the mafia, almost The Sopranos of its day. Nicholson is super-cool as the mid-ranking wiseguy falling in love with a beautiful woman (Kathleen Turner). Then they are contracted to whack each other.
17. The Shooting and Ride in the Whirlwind (1966)
Monte Hellman shot these microbudget western cult classics back to back in the Utah desert. Nicholson produced and starred in both and wrote Ride in the Whirlwind. In The Shooting, he is the disturbing, black-clad gunslinger who menacingly follows a woman and the two men she has hired to accompany her. In Ride in the Whirlwind, he is a potent part of an outlaw trio.
16. Heartburn (1986)
Alongside his saturnine reputation for thrillers, tragedies, dark sexiness and general atavistic threat, Nicholson has long had a parallel career as the reformable rake in romantic comedies – could he have a heart of gold, despite that mad-bad-and-dangerous-to-know image? Here, he plays opposite another alpha-plus star, Meryl Streep, in Nora Ephron’s autobiographical marital breakup comedy.
15. A Few Good Men (1992)
“YOU CAN’T HANDLE THE TRUTH!” Jack Nicholson’s ferocious Col Nathan Jessup erupts from the court-martial witness stand under questioning from the wide-eyed idealist Tom Cruise, pursuing the suspicion that Nicholson’s high-ranking officer directly sanctioned violence and abuse. Another Nicholson scene-stealer.
14. The Postman Always Rings Twice (1981)
In David Mamet’s take on the classic James M Cain noir, tougher than the 1946 version, Nicholson’s sexy-threat image is cranked up as the drifter who has an obsessive affair with Jessica Lange, the young wife of an old gas-station owner – and agrees to kill him. Lange and Nicholson have a raunchy sex scene on the kitchen table, covered in flour, which the first film’s star, Lana Turner, condemned as “pornographic trash”.
13. The Pledge (2001)
One of the grandstanders of Nicholson’s late-career phase, in which he is settling into paunchy disillusionment, rage, fear, loneliness and a kind of wrecked and desperately salvaged decency. He plays the ageing police detective Jerry Black, who, on his last day on the job, is called to a brutal child murder and promises the distraught mother he will find the killer, which becomes his obsession.
12. As Good as It Gets (1997)
James L Brooks gave Nicholson a huge character turn in his bittersweet romantic comedy-drama constructed around his persona, which by this time had gone past the larger-than-life stage and was something else entirely: a one-man Mount Rushmore of movie stardom. He is the cantankerous novelist with OCD and a need to insult and belittle everyone, including Helen Hunt’s waitress and Greg Kinnear’s gay artist.
11. The Departed (2006)
Nicholson and Martin Scorsese is a mouthwatering combination. The result, although perhaps not the classic everyone hoped for, was a barnstormer. Scorsese remade the Hong Kong movie Infernal Affairs about the parallel lives of a young cop and a criminal undercover in the mob and the police respectively. Nicholson is Frank Costello, the jeering, grinning, snarling capo – the Pavarotti of organised crime.
10. Easy Rider (1969)
This was the movie that established 32-year-old Nicholson’s unique position in movies: intense, distinctive and seductive, the hair already starting to thin and the alligator grin beginning to make itself felt. Nicholson is more than a character player, but hardly a pretty-boy lead. He is the wealthy, alcoholic human-rights lawyer George Hanson, who helps out the two counterculture bikers Peter Fonda and Dennis Hopper, but is always getting thrown in the drunk tank himself.
9. Batman (1989)
Nicholson played the Joker in an era when the superhero franchise wasn’t bigger than the star. He is the supervillain that the others (Heath Ledger, Joaquin Phoenix) were later measured against: the gurning, grinning, purple-clad bad guy whose capering craziness effortlessly upstaged Michael Keaton’s more demure Dark Knight. He is given a preposterous origin myth: this Joker was a mobster and hoodlum called Jack Napier (the JN initials leaning into Nicholson’s bad-boy status) who fell into a chemical vat during a shootout in a pharmaceuticals factory, causing his face to convulse into that hideous grin.
8. The Last Detail (1973)
One of Nicholson’s great outlaw-dissident roles. US Navy Signalman Billy Buddusky, alongside Gunner’s Mate Richard Mulhall (Otis Young), is detailed to accompany a pathetic teenage recruit (Randy Quaid) across the country to a military prison in Maine for an eight-year sentence. They have a week to deliver their man. With crazy, hilarious recklessness, Nicholson decides to show the poor guy a good time before he goes away for his ordeal; inevitably, it involves far more illegality than the relatively petty theft that got the kid into trouble in the first place.
7. The Passenger (1975)
Nicholson is an actor with an intensely American sensibility, but he made one of his best films with that European mandarin of high arthouse cinema, Michelangelo Antonioni. The Passenger is a Greeneian tale of a world-weary reporter in Chad. Depressed about his life, he switches identities with a dead man in a neighbouring hotel room. The man turns out to be an arms dealer. Nicholson’s existential antihero fatalistically embraces his identity, knowing it can lead only to violent death, which he accepts with ecstatic calm.
6. The Shining (1980)
“Heeeeeere’s Johnny!” Generations who have no idea who Johnny Carson is know this is the blood-curdling cry of Nicholson’s Jack Torrance as he axes down a door, the grinning psychopath made legendary by the movie’s poster showing Shelley Duvall’s fear-stricken face on the opposite side. They are the couple with a young son who become the off-season caretakers of the remote Overlook hotel – and are plunged into the horror sense-memory that saturates the building. Stephen King was unimpressed by this adaptation; some argue that, like the famous closing image of Nicholson, it effectively froze the actor into a crazy-guy persona that was difficult to shake. But the destructive power of his performance is undeniable.
5. One Flew Over the Cuckoo’s Nest (1975)
The producer, Michael Douglas, had the difficult task of telling his dad, Kirk, who had created the role on stage, that it would be going to Nicholson for the movie. Nicholson made the role iconic and it made him a megastar – a cousin to his character from The Last Detail. He is the rock’n’roll wildman McMurphy, sent down for statutory rape, whose troubled personality gets him a transfer to a mental institution. He leads a revolt against the clinical regime and faces off with a worthy opponent: the terrifying Nurse Ratched, played by Louise Fletcher.
4. The King of Marvin Gardens (1972)
Bob Rafelson’s underrated masterpiece and jewel of the American New Wave features a wonderfully subtle and introspective performance from Nicholson – the kind that he was later increasingly unwilling or unable to attempt. He is David, a gloomy and self-important radio talkshow host in Philadelphia, given to long, literary, self-indulgent monologues about his life and opinions. Bruce Dern is his rackety and disreputable brother, Jason, who is dating a former beauty queen played by the excellent Ellen Burstyn, who needs David to come to Atlantic City and bail him out of jail. The odd-couple energy between Nicholson and Dern is palpable and their dialogue is a joy.
3. Chinatown (1974)
Nicholson’s performance as the Los Angeles private detective Jake Gittes in this remarkable 30s neo-noir from Roman Polanski was worthy of Bogart – although hyperactive in a way Bogart wasn’t. He gave us another famous image: the slashed and bandaged nose, showing you what happens to people who stick their noses into dangerous business. This louche and seedy gumshoe, in his white suit, falls in love with the mysterious shady lady Evelyn Mulwray (Faye Dunaway), whose troubled psychology is at the centre of the film’s plot as Nicholson’s detective investigates a corrupt conspiracy in California’s Department of Water and Power. Yet there is something poignant, even tragic, in this tough guy’s inability to grasp the swirl of sexual dysfunction that lies beneath everything: the insoluble Chinatown of the title.
2. About Schmidt (2002)
This poignant Alexander Payne tragicomedy is Nicholson’s late-career masterpiece; he described it as the most free from egotism he has ever performed. He is Warren Schmidt: an angry, disappointed, depressed old widower who had always secretly resented being chivvied by his late wife, who had made him sit down on the lavatory to urinate; the sight of Nicholson actually doing this on screen is awe-inspiring. Schmidt finds himself on a mean-spirited mission to sabotage his grownup daughter’s wedding to a man he doesn’t like, but he is also making regular charity donations to a disadvantaged six-year-old in Tanzania. Having been encouraged to enclose a personal letter with each payment, Schmidt finds that this has become a journal of self-expression and self-inspection. For the first time, he is thinking about what his life means.
1. Five Easy Pieces (1970)
Here is the single devastating performance that seems to give us all of what makes Nicholson such a radioactive screen presence: the truculence, the sexiness, the insolence, the irrepressible wit and craziness, the unexpected sensitivity, the sadness, the anger and the desolate self-reproach. He is Bobby Dupea, a failed classical pianist who, in his resentment and rage at his own aborted career, abandons his vocation and refined upper-middle-class family to become an oil-rigger out west, trapped in a toxic relationship and hanging out with people who have no idea of what he used to be. His snarky, needling manner comes out in that memorable scene where he mocks a waitress for the apparent difficulties in meeting his demand for toast. Finally, Bobby must come home (with his girlfriend) when his father has a stroke. His angry, painful encounter with his home and his past is unforgettable.
• This article was amended on 28 April 2023. Nicholson was not the co-writer of Easy Rider as stated in an earlier version.
