Jack Nicholson Officially Retires: Ranking The Legend’s 10 Best Films

Jack Nicholson has officially retired from acting after 60 years in the business. Sure, one reaction might be “yeah didn’t he kind of already retire?” Well, now it’s official, and we won’t be seeing anything else from one of Hollywood’s greatest, most unconventional leading men. Nicholson’s career has had some fascinating ups and downs, but no matter how his films may have failed, he always had another hit just around the corner. One of his underrated talents as an actor was his ability to reinvent himself for his audience.

Here are the 10 greatest Jack Nicholson roles, from this humble writer (with a shoutout to Wolf, a ridiculous movie that will always hold a special place in my heart for it’s campy brilliance):


George Hanson, Easy Rider

Jack Nicholson

Nicholson’s breakout role came in Dennis Hopper’s freewheeling look at two bikers driving across the country in the dying days of the hippie movement. While this was more a story about Hopper and Peter Fonda’s rebel, Wyatt, it was Nicholson, as buttoned up attorney George Hanson, that broke apart the otherwise listless story. Of all this film’s importance in cinematic history, there’s no more iconic a shot from it than the sight of Nicholson, blasted on dope, riding on the back of a motorcycle in a football helmet.

Buddusky, The Last Detail

Jack Nicholson

Hal Ashby’s story about two Navy men tasked with bringing a young officer to prison tapped perfectly into Jack Nicholson’s rebellious streak and his fiery madman persona he would take to eleven several times in his career. His character is Buddusky, one of the officers who decide to show this poor bastard, played by Randy Quaid, one last good time before he goes behind bars. While the movie itself hasn’t aged that well, Nicholson’s performance remains the brightest spot.

Melvin Udall, As Good As It Gets

Jack Nicholson

The handling of OCD may forever hamstring this James L. Brooks crowdpleaser and keep it in a 90s vacuum, before everything was offensive. But Nicholson’s Oscar-winning portrayal of eccentric author and obsessive curmudgeon Melvin Udall has more saccharine charm and winning spirit than anything in his career. Nicholson steps outside his suave leading man comfort zone here and it pays off fairly well.

Warren Schmidt, About Schmidt

Jack Nicholson

Just a couple of years after stepping outside his comfort zone in As Good As It Gets, Nicholson took this new senior citizen persona even further with Alexander Payne’s most underrated film, About Schmidt. Here, Nicholson plays a retired Midwestern dolt, a cheap and lazy old man who takes his RV on the road after his wife dies. The role earned him his last Oscar nomination, and was well deserved because without complete dedication to playing this schlub, the film would have easily fallen into self parody.

Garrett Breedlove, Terms of Endearment

Jack Nicholson

James L. Brooks’ Best Picture winner is often pigeonholed as a melodramatic tearjerker, no better than a Lifetime terminal illness movie. But it is so very much more than that, and it’s partially due to Jack Nicholson (and powerhouse performances from Debra Winger and Shirley MacLaine). this was the first time Jack checked his vanity at the door to play an aging, womanizing astronaut. He let his gut hang out, he showed off his thinning hair, but he never got rid of any of his signature charm. It’s a wonderful performance, and one that brings much needed balance to the story.

J.J. Gittes, Chinatown

Jack Nicholson

Nicholson fills out those 40s-era suits as well as anyone in Roman Polanski’s noir masterpiece. His J.J. Gittes is a man who finds himself in over his head when he begins to investigate a water shortage in the City of Angels, only to discover an unsettling story of incest and power brokering which runs deeper and has spun too far out of control. Gittes gets his nose almost sliced off early on, forcing Nicholson to act almost the entirety of the film with some sort of bandage on his nose. It’s an iconic look for an iconic performance.

The Joker, Batman

Jack Nicholson

The late 80s had been a tough time for Nicholson’s career. His list of films is fine, but nothing was gaining much traction at the box office. His star was fading, so he took a chance on a silly kids movie: a dark adaptation of Batman. He would be the Joker, and his electric performance would introduce him to an entirely new legion of fans. It was a renaissance for Jack, and he rode it through a pretty terrific resurgence all throughout the 90s.

Jack Torrance, The Shining

Jack Nicholson

If you need any concrete evidence that the Razzies are a sad and ridiculous “awards,” look no further than the nominations The Shining received back in 1980. Thankfully, nobody cares about the stupid Razzies, and The Shining became one of the most influential horror films of all time. Thanks in no small part to Jack Nicholson’s increasingly unhinged performance. It’s completely insane, but completely contained within a hotel percolating with more and more insanity.

Robert Dupea, Five Easy Pieces

Jack Nicholson

Often times lost amid all of Jack Nicholson’s terrific work in the 70s, and all the game-changing work that shaped cinema in that decade, is one of his greatest performance in Bob Rafelson’s small little drama, Five Easy Pieces. Nicholson’s Robert is a prodigy, an upper-crust classical pianist who has ditched that high tone world for the low-rent, disposable life of a bar-hopping, womanizing oil rig worker. It’s a great character and a fascinating performance from Nicholson, one of the rare instances where he plays nuance and subtlety in lieu of loud theatrics.

R.P. McMurphy, One Flew Over the Cuckoo’s Nest

Jack Nicholson

If Easy Rider was Jack Nicholson’s coming out party, One Flew Over the Cuckoo’s Nest, his first of three Oscar-winning roles, was an announcement that Jack was going to be here for a while. And causing a ruckus in Hollywood. His McMurphy is the audience’s anti-establishment inroad to a story about an oppressive, evil nurse keeping the nuts in the nuthouse under her thumb. His performance is all fire and energy and electricity from start to finish, all the way to the tragic final moments when a lobotomy lets us know the system always wins in the end.

Larry Taylor - Managing Editor
Larry Taylor - Managing Editor
Larry is the managing editor for Monkeys Fighting Robots. The Dalai Lama once told him when he dies he will receive total consciousness. So he's got that going for him... Which is nice.

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