The 10 Best Jack Nicholson Movies Ever

While this wasn’t his biggest role, Nicholson certainly stood out as the masochistic dental patient Wilbur Force in this horror-comedy by legendary shlockmeister Roger Corman. Despite occurring early in his life, Nicholson still displayed the offbeat charisma and taste for the eccentric that would define his later career.

If ever a movie captured the zeitgeist of the 60s era, it’s this classic road movie written and directed by Dennis Hopper. Although Nicholson doesn’t play one of the three titular motorcyclists, his turn as a good-natured alcoholic ACLU lawyer stands out in a film already notable for its career-making performances.

One of my all-time favorite movies, this Roman Polanski classic turns the film noir genre on its head by telling the tale of hard boiled private investigator Jakes Gittes, whose involvement in a dispute over California water rights (based on the real-life California Water Wars) soon exposes him to the depths of plutocratic greed and human depravity. Capped off by one of the most shockingly bleak endings ever filmed, Gittes continues to be one of Nicholson’s most memorable roles.

Based on the counterculture masterpiece by Ken Kesey, this Academy Award-winning film by Milos Forman established the “societal rebel stuck in a mental hospital” template that has been ripped off by so many lesser films ever since. Likewise, when actors attempt to engage in “Oscar-bait” performances by playing free-thinking spirits who “stick it to the establishment,” they’re usually channeling Nicholson’s acclaimed depiction of Randall P. McMurphy here.

Jack Nicholson as a violent lunatic? What a stretch!

Kidding aside, the very fact that Nicholson seems like such a shoo-in today for any role requiring a colorful, terrifyingly insane antagonist is because of his masterful depiction of brooding writer Jack Torrance in this Stanley Kubrick horror film. While it received mixed reviews upon its initial release, subsequent scholarship has been much more favorable, with this movie nearly always appearing in any list of the best work from either Kubrick or Nicholson.

While not one of his better-known roles, it’s hard to imagine a better casting choice than that which landed Nicholson in the role of Satan for this movie. Unlike Jack Torrance, however, the ostensible villain here is actually somewhat sympathetic, with director George Miller helping Nicholson capture Lucifer’s charm and (dare I say it) humanity as well as his pure devilishness.

Nineteen years before millennials were mesmerized by Heath Ledger’s iconic depiction of The Joker in “The Dark Knight,” Generation X-ers were similarly blown away by Nicholson’s performance in the same role in “Batman.” Although some have argued that Nicholson’s Joker has been overshadowed by Ledger’s updated take, it’s almost impossible to imagine Ledger having the comfort to stray from Cesar Romero’s campy precedent (to say nothing of Mark Hamill doing likewise in the Batman animated series) without Nicholson clearing the way for them.

Earning him an Academy Award nomination for Best Supporting Actor, Nicholson’s portrayal of overzealous Marine Colonel Nathan R. Jessup is best remembered for its quotable dialogue (“You can’t handle the truth!”) That said, in this era of right-wing reactionism and neo-imperialist military excess, the callous logic used by Jessup to rationalize his criminal disregard for human life continues to ring chillingly true.

“Ivan Ilych’s life had been most simple and most ordinary and therefore most terrible.”

This quote from Leo Tolstoy’s “The Death of Ivan Ilych,” though not directly referenced in Alexander Payne’s existentialist ode to comic melacholia, sums up its central theme quite perfectly. As the mediocre and forgettable actuary Warren Schmidt, Nicholson brilliantly played against type with his disturbingly convincing account of a man who is gradually realizing that his life is not only nearly over, but has amounted to almost nothing.

Martin Scorsese was long overdue for an Oscar when the Academy finally honored him for this film, and although Nicholson wasn’t nominated for his work playing Boston mob kingpin Frank Costello, his ability to tap into the spirit of real-life mobster Whitey Bulger (on whom Costello was based) is still electrifying. Even in a cinematic market glutted with organized crime stories, Costello stands out as one of the most memorable big bad bosses to appear in multiplexes.