By Megan Riedlinger
7:00am PDT, May 3, 2024
15. Jerry Black in "The Pledge"
In Sean Penn's "The Pledge," Jack Nicholson took on the role of retiree Jerry Black, a former detective who's obsessed with catching a killer. Though the 2001 film was star-studded — Helen Mirren, Robin Wright Penn, Patricia Clarkson and Mickey Rourke also appeared — it bombed at the box office, earning well below its $35 million budget. Despite audiences not clicking with the content, critics loved the film.
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14. Francis Phelan in "Ironweed"
The 1987 movie "Ironweed" — a tragic flick set during the 1930s depression — starred Jack Nicholson and Meryl Streep. He played Francis Phelan, a retired baseball player, and his work was praised by critic Roger Ebert, who wrote, "Nicholson and Streep play drunks in 'Ironweed,' and actors are said to like to play drunks, because it gives them an excuse for overacting. But there is not much visible 'acting' in this movie; the actors are too good for that." It earned Jack best actor nominations at both the Academy Awards and the Golden Globes.
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13. Billy Buddusky in "The Last Detail"
1973's "The Last Detail" was another movie that scored Jack Nicholson an Academy Award nomination for best actor. The flick focused on men in the Navy and saw him play Signalman First Class Billy Buddusky — a performance that earned him rave reviews. Variety wrote that Jack was "outstanding at the head of a superb cast." He ended up winning a BAFTA Award for his work in the film.
12. Jonathan Fuerst in "Carnal Knowledge"
Jack Nicholson took on the role of a womanizer in 1971's "Carnal Knowledge," playing Jonathan Fuerst, an Amherst College student. At the time, critic Roger Ebert raved about the film and its star, calling Jack "the most interesting new movie actor since James Dean." Jack earned a Golden Globe nomination for best actor for his work in the project, which has three parts and follows Jonathan and roommate Sandy (played by Art Garfunkel) from college to middle age.
11. Eugene O'Neill in "Reds"
Jack Nicholson starred in the historical drama "Reds" in 1981 as playwright Eugene O'Neill. Aside from scoring him a best supporting actor nomination at the Academy Awards, the film overall received a lot of critical acclaim. It was the 13th highest grossing film that year.
10. Warren Schmidt in "About Schmidt"
In the 2002 dark comedy "About Schmidt," Jack Nicholson played retired Nebraska insurance executive Warren Schmidt. The actor had to transform physically for the role — namely by sporting an unfortunate comb-over — and earned himself an Oscar nomination and a Golden Globe Award in the process. Critic Roger Ebert raved about Jack's work in the film, writing for the Chicago Sun-Times: "That Jack Nicholson makes this man so watchable is a tribute not only to his craft, but to his legend: Jack is so unlike Schmidt that his performance generates a certain awe."
9. Bobby Dupea in "Five Easy Pieces"
Jack Nicholson's first Academy Award nomination came thanks to his work in "Five Easy Pieces," the 1970 film in which he played Bobby Dupea, an oil worker who hails from an upper-class family. The film scored four Oscar nominations and was added to the National Film Registry of the Library of Congress back in 2000.
8. Colonel Nathan Jessup in "A Few Good Men"
1992 saw Jack Nicholson stepping into the role of Base Commander Colonel Nathan Jessup in the legal drama "A Few Good Men." The drama, which is centered around the murder of a Marine, follows Jack's character and his alleged role in the act. His work earned him a best supporting actor nomination at the Academy Awards.
7. Garrett Breedlove in "Terms of Endearment"
"Terms of Endearment" was another box office success for Jack Nicholson — and this one earned him an Academy Award too! He played Garrett Breedlove, a retired former astronaut in love with Shirley MacLaine's Aurora Greenway in the 1983 James A. Brooks film. He picked up a best supporting actor Academy Award for his performance — one of five Oscars the movie earned.
6. Jake Gittes in "Chinatown"
As private eye Jake Gittes, Jack Nicholson wowed in "Chinatown." The 1974 flick — which earned an Academy Award for best screenplay and co-starred Faye Dunaway — is loosely based on the scandals of real-life Los Angeles Department of Water and Power chief engineer William Mulholland, who was renamed Hollis Mulwray in the flick.
5. George Hanson in "Easy Rider"
In 1969, Jack Nicholson got his first big acting break playing lawyer George Hanson in "Easy Rider." The performance was so impressive that it would end up earning Jack his first Academy Award nomination for best supporting actor. He starred alongside Peter Fonda and Dennis Hopper in the film, which became the fourth highest grossing movie of 1969 and started him on the path to superstardom.
4. Melvin Udall in "As Good As It Gets"
Next up, a different type of film for the iconic actor! In 1997, Jack Nicholson starred in "As Good As It Gets," a romantic comedy that earned him an Academy Award and a Golden Globe for best actor. He starred as novelist Melvin Udall, a man who suffers from obsessive-compulsive disorder who's in a complicated relationship with Helen Hunt's character, Carol Connelly.
3. The Joker in "Batman"
Time for a blockbuster! Jack Nicholson earned a pretty penny for his work in 1989's "Batman," in which he took on the iconic character The Joker. In return, he scored a record-high salary that was reported to be around $50 million. The Tim Burton superhero flick became the fifth highest grossing movie in history at that time as it took in more than $400 million at the box office.
2. Jack Torrance in "The Shining"
One of Jack Nicholson's most famous roles came in 1980 when he starred in "The Shining." The 1977 Stephen King horror story got the big-screen treatment, with Stanley Kubrick directing and Jack starring as Jack Torrance, a homicidal writer. Though it received mixed reviews, it did well at the box office and went on to become one of the most beloved horror films in history, ranking 29 on AFI's "100 Years… 100 Thrills" list in 2001.
1. Randle McMurphy in "One Flew Over the Cuckoo's Nest"
Jack Nicholson's turn in "One Flew Over the Cuckoo's Nest" is one of the most memorable of his entire career. He played mental hospital resident Randle McMurphy — the role almost went to Marlon Brando — in the 1975 film, which is based on a novel by Ken Kesey. The performance scored him an Academy Award. The movie is considered by many critics to be one of the best films of all time.
