Celebrate Jack Nicholson’s Birthday With This Ranking of His 10 Greatest Roles

Can you handle the truth?

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This April 22nd marks Jack Nicholson‘s 81st birthday. To celebrate one of the best actors of all time, the master of old school cool and an inspiration to all those out there who just don’t give a fuck, we salute the one and only Jack with a definitive list of his 10 best roles. 

10. The Shining (1980) – Jack Torrance

All work and no play might make Jack a dull boy but there wasn’t anything dull about the intensely eerie, violent performance that Nicholson put in for the screen adaptation of Stephen King’s hotel horror story. His haunting stare that ends the movie stayed with us long eng after the end credits rolled. 

9. One Flew Over the Cuckoo’s Nest (1975) – R.P. McMurphy

Jack’s first Oscar win came from his portrayal of a mental patient in the excellent movie adaptation of Ken Kesey’s 1962 novel. His performance here deserves every accolade it’s gotten but winds up at the back of our list because it’s legitimately hard to watch. Jack’s role as McMurphy is so utterly tragic that, after rooting for him and the other patients all movie, it was heartbreaking to see him lose (his mind) in the end. 

8. Easy Rider (1969) – George Hanson

The first role that earned Jack the attention of the Academy was for a supporting actor in the great American road trip story that is the classic, Easy Rider. As the alcoholic lawyer exploring drugs for the first time with a couple of interesting conspiracy theories to share, Jack made a lasting impression. 

7. Five Easy Pieces (1970) – Robert Eroica Dupea

Only Jack could deliver a line like “I want you to hold [chicken salad] between your knees.” and seem like a lovable asshole anyway. As an ex-prodigy coming to terms with his wayward life, his role in Five Easy Pieces is one that only a guy like Jack could pull off. 


6. Batman (1989) – The Joker

“Have you ever danced with the devil in the pale moonlight?” Jack has. As the Joker in Tim Burton’s blockbuster, Jack defined the modern villain, mixing psychotic tendencies with dark humor to set the high water mark for all actors looking to channel their inner maniac for years to come. 

5. The Last Detail (1973) – Buddusky

Rocking an era-appropriate mustache, Jack’s take on a naval prison escort is a brawler with a heart of gold. The movie, which tells the story of a young man’s last eight days of freedom before doing time, is the perfect mix between The Hangover and 25th Hour. It’s a must-watch role from the master of partying hard and hitting harder, on-screen and off. 

4. The Departed (2006) – Frank Costello

In an ensemble cast of heavy hitters, Jack once again is the shining star. His portrayal of Frank Costello is calculating and menacing, combining the two like only Jack can. It’s a role that’s unforgettable for the guy and makes us wish that Jack and Scorsese had started working together much, much sooner. 

3. As Good As It Gets (1997) – Melvin Udall

Jack’s latest Academy Award win came from his portrayal of an OCD novelist who’s as wretched as he is famous. But it’s the journey Jack takes us on through this movie — one that leaves him wanting to be a better man — that makes this role one of his best. He also taught us that tempting our love interests with late-night bakery visits for freshly baked bread was an absolutely clutch romantic move. 

2. Chinatown (1974) – JJ Gittes

Roman Polanski’s neo-noir mystery set in the backdrop of LA is an edge-of-your seat thriller where Jack’s private detective, Gittes, digs up a determined, hard-boiled edge. Murder and double-cross don’t phase Jack in one of the best tough-guy roles he’s ever played. 

1. A Few Good Men (1992) – Col. Nathan Jessup

A testament to just how fucking awesome Jack is as an actor, his role as Colonel Nathan Jessup meant just a few minutes on-screen and just 10 days shooting but it also got Jack one of his many Oscar-nominations. The infinitely-quotable, now-famous speech was performed by Jack some 40 or 50 times (at full-intensity) before they wrapped but it was worth it since Jack outshines every single person in an otherwise star-studded cast of Tom Cruise, Demi Moore, Kevin Bacon and Kiefer Sutherland.