The best Jack Nicholson roles of all time

Nicholson was a household Hollywood name in the early 1970s, but one of his more underrated roles came in this Bob Rafelson-directed drama. He stars as a depressed cynic who teams with his estranged brother (Bruce Dern) to potentially make a lot of money in Atlantic City. Though David is not the most cheery character Nicholson has ever played, his interaction with Dern's Jason is a consistent highlight of the movie.

Sure, this is far from Nicholson's best movie. Maybe because his co-star Adam Sandler helped bring it down. That's for another argument. But Nicholson can do comedy, and he's certainly one of the highlights as the unorthodox therapist who resorts to some "radical round-the-clock therapy" to help Sandler's Dave Buznik deal with his apparent, and likely overblown, anger issues. 

This is the first of two movies on this list that Nicholson worked under the direction of fellow Hollywood legend Sean Penn. Freddy Gale is spiraling father still haunted by a drunk-driving accident that claimed the life of his daughter. Now, the person responsible for her death is being let out of prison, sparking Gale to seek revenge. While it's not a unique storyline, Nicholson deliciously sinks his teeth into the character from what is his one true indie film performance.

Nicholson's first film in the 2000s sees him play a Reno police detective determined to solve the murder of a child. To the casual Nicholson fan, the role is probably not on many radars. That is despite the fact Sean Penn directed the picture, which featured a stellar ensemble cast including Helen Mirren, Vanessa Redgrave, Sam Shepard, and Benicio del Toro. Critics praised the mustached-Nicholson's powerfully subtle performance.

This was Nicholson's fourth film appearance, and critics consider it to be his breakout role. Described as a masochist or sexual deviant, Wilbur enjoys going to the dentist and is a big fan of getting his cavities filled. Especially during that one certain visit when Seymour, himself, does the honors of catering to Wilbur's penchant for pain. Never afraid to push the envelope and act outside of the box, Nicholson essentially set the tempo for the eccentricity of the characters down the road.

The mysteriously eccentric Daryl Van Horne is rather irresistible to witches Alexandra (Cher), Jane (Susan Sarandon), and Sukie (Michelle Pfeiffer) — at least to start. His tactics are quite manipulative. The movie made nearly $64 million at the box office in North America, and several visual and sound aspects of the film were praised. Of course, amid the on-screen star power, Nicholson stood out above the rest, despite the urge to loathe his character.

When it came to playing a real-life figure, Nicholson did not skip a beat. As the infamous Teamsters boss, Nicholson does a strong job of hitting the mark. He never had a problem playing an unabashed smarmy character who has no issue with pushing boundaries and leaving some physical, mental, or monetary carnage behind. No challenge seemed too big for Nicholson to handle, and this is a perfect example of him nailing the intricacies that come with playing such an appealing role.  

More comedy from Nicholson, who plays incompetent President of the United States James Dale in Tim Burton's science-fiction farce. Dale displays few moments of leadership, has no real answer for the Martians who have taken over Earth, and tries to pass himself off as intelligent. However, the man can make a speech. Whether trying to comfort the world or prove something to a group of Martians that want to see his demise, his theatrics are among the highlights of this cult classic.

Nicholson had already been nominated for two Academy Awards when he took on the lead role in this Mike Nichols' classic. Even amid Hollywood heavyweights like Ann-Margret, Candice Bergen, and Rita Moreno, Nicholson "carries the film," as stated by late renowned critic Roger Ebert. Playing the extroverted, sexually charged Fuerst, Nicholson and Art Garfunkel, who plays his more passive roommate Sandy, both earned Golden Globe Award nominations for the movie, while Margret won the award for Best Supporting Actress — Motion Picture.

There was plenty of hype surrounding Batman hitting the big screen in the late 1980s, and while Michael Keaton stepped into the role of the Caped Crusader, it was Nicholson, as the notoriously iconic Joker, who essentially stole the show. Perhaps too much. As several film critics at the time thought, the darker version of the campy criminal overshadowed the good work displayed by some of his co-stars. Still, this remains one of Nicholson's most popular roles and earned him a Golden Globe nomination.  

A Best Actor Academy Award nomination was well earned for Nicholson in this film version of William Kennedy's Pulitzer Prize-winning, Depression-era novel of the same name. Playing principle antagonist Francis Phelan, Nicholson is riveting as a homeless alcoholic. He's still haunted from a tragic past but looking to reunite with his estranged family. Meryl Streep, to no surprise, is equally superb as Francis' sickly lover and drinking pal. A Hollywood pairing that exudes greatness.

Warren Beatty earned his just praise for co-writing, directing, and starring in this critically acclaimed historical drama. Yet Nicholson, who is exceptionally passionate and powerful as legendary playwright Eugene O'Neill, is hardly overshadowed. Much like fellow co-stars Diane Keaton and Maureen Stapleton — all of whom were nominated for Academy Awards on the picture. It was the first such accolade for Nicholson in six years and second overall for a Best Supporting Actor role.

Nicholson's first Academy Award nomination came for Best Supporting Actor in this celebrated biker drama that featured Peter Fonda and Dennis Hopper in the leading roles. He didn't win that Oscar, but was quite memorable as the alcoholic lawyer who helps the two stars' characters get out of jail. He then throws his inhibition, and rather square lifestyle, out the window by joining the two bikers on their trek to New Orleans. Though, as it turns out, it wasn't the best idea.

The better of Nicholson's two film performances from 2003. Well-off record company owner Harry Sanborn lives the good life, which includes a preference for younger women. Like Marin (Amanda Peet). That is, until he meets her mother, Erica Berry (Diane Keaton). Though Harry can be arrogant and full of himself, Erica seems to bring out his vulnerabilities and need to be loved — and have someone to love. Nicholson doesn't necessarily seem right for the rom-com scene, but was impressive enough to earn a Golden Globe nomination for this performance. 

Another Best Actor Oscar nomination for Nicholson. He stars in this comedy-drama about two Navy officers (Nicholson and Otis Young) escorting a Seaman (Randy Quaid) to a Naval prison in Maine. On the way, the trio enjoys plenty of debauchery, moments of comradery and some tense times. A still rather young Nicholson feels right at home in this seemingly confined, yet carefree character. As an actor, Nicholson was only get better and moving closer to his spot among Hollywood's top leading men.

The most recent of Nicholson's films to make this list. Amid a star-studded cast (Matt Damon, Leonardo DiCaprio, Mark Wahlberg, Martine Sheen, Alec Baldwin), an up-in-age Nicholson proved once again he can shine bright. Frank Costello is a ruthlessly witty and deadly Irish mob boss. He demands loyalty, but he's rather protective of those from his past — and rewarding, as long as you scratch his back. He was nominated for Best Supporting Actor Golden Globe, his last such honor.

When it comes to Nicholson's greatness in this John Huston-directed dark comedy, credit must also go to co-stars Kathleen Turner and Angelica Huston (who won a Best Supporting Actress Oscar for the movie). In this tale of mafia assassins (Nicholson and Turner) who fall in love and eventually are hired to kill each other, the dynamic between the trio is truly special. Nicholson, nominated for another Best Actor Oscar, is actually appealing and rather charming in the role — despite his profession. 

Nicholson has a knack for excelling when playing eccentric, almost mysterious, film characters. Private Investigator Jake Gittes, if anything, is a character. And another icon portrayed by Nicholson, who earned a Best Actor Oscar nomination for starring in Roman Polanski's neo-noir crime drama. This film, like others on this list, has been considered among the best movies of all time. Perhaps the greatest trait of any actor is when the audience has no choice but to feel for their character — anything, good or bad. Nicholson's certainly among the best at getting that done.

This was the last role for which Nicholson earned an Oscar nomination (Best Actor), and it's certainly worthy of such praise. Warren Schmidt seems bored since retiring from a successful job, and even more lost following the unexpected death of his wife. More issues arise, which at times prove too much for Schmidt to handle, and he essentially gives up on life. It's a vulnerable role for Nicholson in this Alexander Payne dark comedy drama. Of course, it's hard not to root for the a guy like Schmidt, despite his many flaws.

Of all the memorable characters Nicholson has played during his legendary career, the obsessive-compulsive Melvin Udall might be the most unsettling — at least to start. And that's saying a lot. Eventually, though, through time spent with his gay neighbor (Greg Kinnear) and favorite waitress (Helen Hunt) at the restaurant where he eats breakfast, Melvin begins to let his guard down and embrace a simple life he likely wasn't aware existed. Both he and Hunt won Oscars for their roles — the last such victory for Nicholson. 

It's funny how things tend to work. As Hollywood lore goes, the part of the Aurora Greenway's arrogantly charming, retired astronaut-neighbor Garrett Breedlove was written by Terms of Endearment director James L. Brooks for Burt Reynolds. The superstar actor turned it down, as did Harrison Ford and Paul Newman. Nicholson eventually landed the role of Shirley MacLaine's on-screen love interest. And, he delivered the quintessential supporting performance — not over-the-top but truly memorable. Offering humor, tension, and compassion in this unforgettable drama that earned Nicholson his second Oscar win.

There were film critics at the time who felt Nicholson's role here, as a well-to-do piano prodigy who decides to work on an oil rig, was the moment he went from talented, respected actor, to star-making. Five Easy Pieces not only showed the depth and emotional intensity Nicholson was capable of delivering, but resulted in his first Academy Award nomination for Best Actor. He did not win, but it began a string of four Best Actor nominations for Nicholson during the 1970s. 

Though The Shining is one of Nicholson's most recognizable movies, and the writer-turned-madman Jack Torrance is one of the most iconic literary and film characters, neither earned any Oscar or Golden Globe nominations upon its release. Yet, when it comes to horror flicks, The Shining, which did deviate from Stephen King's book form, is one often hailed among the best of all time. Meanwhile, Nicholson's performance continues to be talked about and highlighted. "Here's Johnny!!!"

Nicholson's final Best Supporting Actor Oscar nomination came for this classic military legal drama, Rob Reiner-directed film starring Tom Cruise. However, it's the arrogant, gung-ho, do-as-I-say Marine Colonel Nathan Jessup who is responsible for some of the best movie lines of all time. And that's not a stretch to say. He's mocked by Cruise's slacker lawyer Daniel Kaffee, in Nicholson's voice. A basic cable staple, A Few Good Men, and Nicholson, specifically, is why we always seem to watch when it's aired.

This wasn't an easy call, but it's hard to argue just how special Nicholson's performance was in the Miloš Forman comedy-drama that dominated the Oscars in 1976. It's often hailed among the greatest movies of all time. Nicholson, obviously, is a major reason why, as the rebelliously witty and loyal mentally institutionalized Randle McMurphy. His rivalry with hard-nosed, intimidating nurse Ratched (Louise Fletcher) provides some of the film's best moments and paved the way for Nicholson's first Academy Award victory for Best Actor.