Jack Nicholson is living proof that attitude has no expiration date. The three-time Oscar winner (and record holder for most nominations for a male actor at twelve) has a lengthy list of terrific roles. Not bad for someone who got his start in low-budget hippie exploitation pictures and Roger Corman adaptations of Edgar Allan Poe stories.
Nicholson has turned in so many great performances that to list the ten best means you end up skipping his work as a screenwriter (The Monkees' movie Head); as director (college basketball film Drive, He Said); one of his Oscar winners (As Good As It Gets is merely good, not great, sorry); and the one where he floated by exclusively on charisma (The Witches of Eastwick is iconic, but really doesn't hold up.) Also getting a miss, the movie with his most famous line, “between your kneeeees,” because the essence of what makes Five Easy Pieces good is represented in some other, better films.
Easy Rider (1969)
On paper, it looked like another typical gig for Nicholson. He was well familiar with hippie drug culture movies (Psych-Out and The Trip) and biker flicks (Hells Angels on Wheels) but Easy Rider was different. It wasn't made from without, but from within. Dennis Hopper, Peter Fonda and co-writer Terry Southern were going to show square America what was really happening in the counter-culture, man. And Jack was actually going to represent the outsider! His drunken, goofy small-town lawyer with readymade catchphrases (“Nic! Nic! Nic! INDIANS!”) was just the comic relief this movie needed to be both quintessential and entertaining.
Carnal Knowledge (1970)
American culture is still catching up with the themes of Mike Nichols's dark masterpiece about the destructive power of sexual obsessions. Written by satirical cartoonist Jules Feiffer (and co-starring Art Garfunkel?) Carnal Knowledge was the first of many films in which Nicholson would pull a switcheroo on the audience, presenting a character that, at first, you think you envy but, by the end, you pity. If you want a vision of Don Draper from the actual period, watch Nicholson devolve from a college skirt-chaser to a wretched hater of women forever trapped in the prison of reliving his own past conquests.
The Last Detail (1973)
It was here, with this brilliant, filthy sailors' comedy where the “Jack” persona truly hit the stratosphere. There's hardly any plot. Nicholson is enlisted in the Navy. He and his buddy (Otis Young) have to escort a kid (young Randy Quaid) to prison for some dopey infraction. As they travel cross-country, it's wall-to-wall drunken hijinks. Yes, the movie, written by Robert Towne and directed by Hal Ashby, certainly works on a metaphorical level about the US military, but forget that for a moment and just enjoy the outrageous and shocking ride.
Another from screenwriter Robert Towne, this love letter to 1940s film noir directed by Roman Polanski is a masterpiece of tone and style. Nicholson is a cunning private eye who gets sucked into a vortex of double-crosses, secrets and political corruption. The story isn't just juicy, it's slick. Even with a bandage over his nose (his nostril sliced in a scene by the director himself) Jack still looks cool in those suits opposite Faye Dunaway. Jerry Goldsmith's brassy score remains one of the best ever created.
One Flew Over the Cuckoo's Nest (1975)
Jack Nicholson was born to play Randle Patrick McMurphy. Maybe he's mentally ill, or maybe he's a wiseguy scoundrel trying to pull a fast one to stay out of prison. Either way, he ends up representing the spirit of the individual in this engrossing, funny and ultimately tragic allegory about how The Man is keeping us down, man. Ken Kesey's rebellious book was perfect material for Czech director Milos Forman, himself a refuge of from a then-repressive state. This fiery, energetic performance won Nicholson his first Oscar.
The Shining (1980)
Would this movie be half as scary without Jack's near-comically arched eyebrows? I say, no. Everything about this confounding soak of pure terror is in its precise place, and while Stanley Kubrick's patented camera moves and Stephen King's eerie setting may be what's most important, it's ultimately Nicholson that has to sell it. I don't think we've ever watched anyone slowly go bananas in a movie quite to perfection as it is done in The Shining.
Reds is probably the least known picture on my list (and, yes, I'm picking it over others from the era like the sexy and smart hitman thriller/comedy Prizzi's Honor). What Nicholson shows us in his portrayal of playwright Eugene O'Neill in Warren Beatty's 3 hour 14 minute epic Reds is his range. Cast somewhat against type as a mild gent with his heart on his sleeve (though still given to the occasional outburst) this is one of our few looks at Nicholson as a beta male, and the dissonance it causes with our expectations works to make the role even richer.
Terms of Endearment (1983)
I hesitated to include this one, because it's a small role and it's one that really just trades on the “ol' Jack” persona established way back with The Last Detail. But, man, it's just too much fun to leave behind. In the midst of James L. Brooks's big weepie family drama, in saunters Nicholson as a retired astronaut (!!?) and Shirley MacLaine's new boyfriend. His job mainly is to be charismatic and to represent hope and excitement and joie de vivre. And for all the big emotional roller coaster moments in the film (it's about mother-daughter relationships, dying young, economic struggles, you name it) it's Nicholson's quiet encouragement to a grieving child that is probably the most touching thing in the whole picture. Oh, God, I'm starting to well-up just thinking about it. Nicholson won his second Oscar, Best Supporting Actor, for this one.
About Schmidt (2002)
Flash-forward a few years and Jack is ready for … retirement? Nestled between Election and Sideways in Alexander Payne's resume is this true gem of a dark comedy. Riffing a bit on the road trip nature of Easy Rider, the flick About Schmidt sends Nicholson en route to his daughter's wedding in a Winnebago, giving him time to reflect on his mediocre and somewhat loveless life. Is there time yet for him to change? This is a movie, what do you think? But don't expect pat solutions. Nicholson still has a touch of deviance to him.
The Departed (2006)
We're not counting Jack out, but as it stands Frank Costello in Martin Scorsese's epic of Boston criminals and cops might be his final truly great role. From the opening frames of Nicholson's tough guy voice over (“I want the environment to be a product of ME!”) set to the shimmery guitar of the Rolling Stones, you can tell this is a loathsome character Nicholson loves to play. He milked every scene and helped lead the movie to win the Best Picture Oscar.