10 of Jack Nicholson’s Most Iconic Roles

Jack Nicholson: an icon of American cinema. Throughout his celebrated career, he’s given audiences terrifying, inspiring and even comical performances capped by three Oscars (One Flew Over the Cuckoo’s Nest, Terms of Endearment, As Good as it Gets).  Now in recognition of his 80th birthday, we take a look at 10 of his most memorable film roles that best exemplify his diverse and storied career.

NOTE: In a career as long and varied as his, there are obviously more than 10 great performances, and ones that are not on this list do not mean they are any less noteworthy. Consider this list a representation of the wide range of characters he is able to play and a tribute to one of the best to ever grace the screen.

Randle McMurphy (One Flew Over The Cuckoo’s Nest 1975)


Nate: Based on the Ken Kesey novel of the same name, this performance is so good it is commonly used in college psychology to demonstrate mental illness. Jack is unhinged here (even more so than usual) as he walks the fine line between comedian, deranged madman and at times surprisingly human philosopher. He juggles these facades with brilliant control that is further amplified by the Jack Nitzsche’s wonderful score hitting home many of the film’s themes. Nicholson would win his first of three Oscars for this role, a well-deserved honor for a masterful performance.

Jack Torrance (The Shining 1980)

Nate: Working under auteur Stanley Kubrick, Nicholson turns in arguably the greatest performance of his career. As Jack Torrance, we witness a man’s slow descent into madness played to perfection by Nicholson. Featuring some of the most iconic scenes in cinema history, it’s place in pop culture is so well known that even those who have not had the pleasure of viewing this masterpiece are at least somewhat familiar with Jack’s performance. Perhaps it was Kubrick’s pursuit of absolute perfection that drove Nicholson to reach a new plateau but if you weren’t aware of him before this performance, you definitely knew who Jack Nicholson was after it.

 The Joker (Batman 1989)

Michael: It’s difficult to determine who played the “best” Joker; indeed with a list that includes Cesar Romero, Heath Ledger, and even Mark Hamill, it’s not really right to say one trumps them all. Every actor who’s portrayed the Caped Crusader’s arch nemesis has brought something unique to the role, and of course, Jack Nicholson is no different. Tim Burton’s film was the first real Batman movie (if you discount the movie version of the Adam West series and some of the serials from the ‘40s) and a departure from the campy nature the character and its villains had taken. Nicholson’s Joker remains a joy to watch; here was a character that combined some of the sillier aspects of the clown killer alongside the criminal mastermind traits. It’s a perfect blend of fun and seriousness. While Ledger’s version was more psychological, Jack brought a sadistic comedy to the character. Playing The Joker was the perfect choice for a man with his unique on-screen abilities.

Frank Costello (The Departed 2006)

Michael: The film that finally won Martin Scorsese his long-overdue Academy Award, The Departed continued the director’s legacy of crafting masterworks in the organized crime genre. Nicholson is Irish American mob boss Frank Costello, a fiery but charismatic leader. In what is occasionally a complex narrative involving ‘moles’, changing allegiances and a slew of anti-heroes, Jack remains consistently entertaining throughout bringing his exuberance and mean side to a great movie.

Warren Schmidt (About Schmidt 2002)


Nate: Jack Nicholson is most known for playing the villain, the angry man who could explode into a firery rage or break into absolute insanity at a moment’s notice. Roles in A Few Good Men, The Shining and Batman are a testament to this but with About Schmidt, Nicholson showcases his ability to play the sympathetic character. In a performance heavy on emotion, director Alexander Payne really allows Nicholson to dwell in the sadness and in that churn out genuine feeling. In the years prior to About Schmidt, Nicholson would appear sporadically in some less than stellar films including Mars Attacks! but this performance proved that Jack can still deliver earning himself his 12th Oscar nomination in the process.

J.J. “Jake” Gittes (Chinatown 1974)

Nate: Nicholson appears in every scene of this Roman Polanski classic and contributes to one of the greatest neo-noir films of all time.  As Private Eye J.J Gittes, Nicholson plays half of the movie with a bandaged nose but that doesn’t stop him from acting his face off (wow that is a horrible joke…I apologize) in a layered performance that intrigues and captures the audience as they uncover the seedy underbelly of Los Angeles alongside Nicholson. It is Jack performance that elevates the film from a standard run of the mill crime drama once again demonstrating why some of the industry’s finest directors from Kubrick to Scorcese want to work with Nicholson.

 Buddy Rydell (Anger Management 2003) 

 Michael: This movie is obviously not a classic by any means, nor is it really a great comedy film. But it does have its share of very funny scenes, and whenever Jack Nicholson is on screen he steals the spotlight from everyone including Adam Sandler. As Dr. Buddy Rydell, a therapist whose own sanity is frequently in question, Jack is a pure delight. He’s suave, devious, and just plain hysterical. He’s like a more benevolent form of The Joker, leaving behind the criminal part, but retaining all the zaniness and joie de vivre. He shows his comedic abilities in fine fashion, and the result is another great character in his wide portfolio.

Robert “Bobby” Eroica Dupea (Five Easy Pieces 1970)

Nate: Everyone needs a breakout film, even Jack Nicholson and Five Easy Pieces was that launchpad for Jack. In this film, we witness some of the early Nicholson nuances and his keen sense of delivery that would later make him a star. His trademark volatility and ability to shift from someone the audience could cheer for to a downright despicable villain is on full display here. This would mark the first of his record-setting twelve Oscars nominations as he would take this and never look back.

 Colonel Nathan R. Jessup (A Few Good Men 1992)

Michael: Based on Aaron Sorkin’s play of the same name, the film version of A Few Good Men features one of the most memorable and parodied scenes in all of cinema. The escalating tension that builds in the courtroom between Nicholson’s and Tom Cruise’s characters comes to a boiling point with the famous “You can’t handle the truth!” quote. As Colonel Jessup, Jack is arrogant, self-assured, and a bully. It’s a great example of his versatility; he can be silly and serious, and often both at the same time (The Joker, One Flew Over the Cuckoo’s Nest as examples). But he’s totally serious and antagonistic as the Colonel. With the great screenplay by Sorkin, this is a solid work of drama and Jack makes the most out of it with another memorable and well-acted role.

Melvin Udall (As Good as It Gets 1997)

Michael: As the misanthropic Melvin Udall, Jack delivers another charming and loveable performance. Sure the character can be mean and antisocial, but it’s his transformation into a man who begins to accept human emotions that make us embrace him. He won his third Oscar for the role at the age of 60, showing he wasn’t about to let his best work be stuck in the past. The part is Jack Nicholson showing his eccentric and blunt side once again, giving a treat to viewers. 

Honorable Mentions:

The Passenger (1975): Another low-key Nicholson performance that shows his quiet side. It’s a film about ennui and the emotional tolls of life as Jack plays with his full actor’s toolbox in this deeper cut from his filmography.