The Essential Jack Nicholson

In this classic film about American counterculture, two motorcycle riding hippies played by Dennis Hopper (who directed the film) and Peter Fonda (who co-wrote the film with Hopper) trek east across the United States from Los Angeles to New Orleans in order to make it to Mardi Gras. En route, the pair see all sorts of wild sights (surely shocking to the square audiences at the time of its release) and pick up a drunk ACLU lawyer played by Nicholson (who earned his first of 12 Oscar nominations for his role), whom the men introduce to marijuana. [Where to stream Easy Rider]

Nicholson and his co-star, Karen Black, were both nominated for Oscars in Bob Rafelson’s drama about a oil rig worker named Bobby Dupea who returns home to his eccentric family of musicians when he discovers that his estranged father is on his deathbed. Soon it’s clear that his erratic behavior is a cover for a lifetime of avoiding connection with those closest to him, including his pregnant girlfriend. [Where to stream Five Easy Pieces]

Nicholson stars as private eye Jake Gittes, who is hired by the beautiful Evelyn Mulwray (Faye Dunaway) to follow her husband, Hollis, whom she suspects of having an affair. When Hollis Mulwray is found dead, Gittes begins to suspect foul play — and wonders if Evelyn or her father, Noah Cross (played by famed director John Huston) are involved in the plot. Roman Polanski’s Oscar-winning neo-noir is a stunning mystery filled with twists and turns. [Where to stream Chinatown]

Nicholson won his first Oscar for the iconic role of Randle Patrick “Mac” McMurphy, a convicted sex offender who exhibits signs of insanity most likely so he could be transferred to the more relaxed environs of a mental institution. It’s there, however, that he meets his match in the stoic and severe Nurse Ratched (played by Oscar-winner Louise Fletcher), who goes to extreme lengths to suppress his rebellious nature. [Where to stream One Flew Over the Cuckoo’s Nest]

You can tell that Nicholson seemed to relish the chance to do an over-the-top performance as the alcoholic writer Jack Torrence who, along with his timid wife and psychic son, holds up in a massive haunted hotel for the winter. Torrence slowly descends into madness, and his violent, paranoid tendencies start to target his family. Nicholson delivers an incredible performance, per usual, in Stanley Kubrick’s horror masterpiece. [Where to stream The Shining]

Nicholson won an Oscar for Best Supporting Actor in the first of four films in which he appeared that were written and directed by James L. Brooks. Here, Nicholson plays the retired astronaut Garrett Breedlove, one of the love interests to Aurora Greenway (Shirley MacLaine) in the film that follows Aurora’s tumultuous relationship with her daughter, Emma (played by Debra Winger). [Where to stream Terms of Endearment]

This dark comedy, based on John Updike’s novel, may seem dated nearly three decades after its release, but it’s still a lot of fun to watch. While its trio of stars (Cher, Susan Sarandon, and Michelle Pfeiffer) deliver sexy and comic performances as the titular witches of the sleepy New England town, it’s Nicholson who steals the show as the fiendishly handsome Daryl Van Horn. [Where to stream The Witches of Eastwick]

Tim Burton’s ambitiously gothic adaptation of the comic book brought us Michael Keaton’s Batman — but, perhaps more importantly, it also gave us Nicholson’s rendition of the Joker. Both classically comedic and sinister, Nicholson’s villain is a surprising turn for the actor, who, once again, seems to be having the most fun of anyone in the film. [Where to stream Batman]

Rob Reiner directs Nicholson alongside Tom Cruise and Demi Moore in this big-screen adaptation of Aaron Sorkin’s stage play. Nicholson plays a hot-headed Marine colonel who may be partially responsible for the murder of a Marine private, who died at the hands of two other soldiers. Nicholson received an Oscar nomination for the role, and famously uttered one of the most memorable lines in American cinema: “You can’t handle the truth!” [Where to stream A Few Good Men]

Nicholson won his third Oscar for the role of Melvin Udall, an obsessive-compulsive and misanthropic novelist in this romantic comedy co-written and directed by James L. Brooks. Forced by fate to show compassion for his ailing gay neighbor (and to take care of his dog, Verdell), Melvin’s severe exterior begins to break — just in time for him to express some true feelings for a waitress at his local restaurant, Carol (played by Oscar winner Helen Hunt). [Where to stream As Good As It Gets]

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