10. The Departed
A great performance as mobster Frank Costello, it’s likely the movie’s all-star cast and overall success — it won the Best Picture Academy Award — made Nicholson’s role seem even stronger. Really, as the No. 10 entry on this list, you could flip a coin and choose several of his other roles, in movies such as The Last Detail and Five Easy Pieces, and pick a Nicholson performance just as worthy of this position.
9. Prizzi’s Honor
One of Nicholson’s strangest roles, in which he played a Mafia hitman who falls in love with his intended target, an assassin hired to kill him (played by Kathleen Turner.) He was nominated for a Best Actor Academy Award, and won the Golden Globe for Best Actor in a Musical or Comedy.
8. Terms of Endearment
Nicholson won a Best Supporting Actor Academy Award for his portrayal of hard-drinking former astronaut Garrett Breedlove. Although this movie featured the mother-daughter relationship between Shirley MacLaine and Debra Winger — who also won awards for their efforts — Nicholson stole the scenes in his limited on-screen time as the love interest of MacLaine’s character. Of course, few in Hollywood history have been better scene stealers than Nicholson.
Michael Keaton had top billing in director Tim Burton’s 1989 film Batman, but Jack Nicholson was the real star in his role as “The Joker.” Nicholson earned critical praise and played a key role in the film’s huge box-office and home video bonanza. He also earned an estimated $60 million in royalties from the movie.
6. The Shining
It’s possible that if you ask the average American who coined the phrase “Heeeeere’s Johnny!” Jack Nicholson’s character in the film The Shining would whip former Johnny Carson sidekick Ed McMahon. Nicholson’s portrayal of a writer descending into madness while he and his family serve as caretakers at a deserted Colorado resort hotel drew yawns from the critics — he was not nominated for a single major award for his performance. But it is one of his best performances, with some of his most memorable scenes.
This was Nicholson’s first big role as star of a major production, in 1974 at the age of 37. Nicholson won several major awards for best actor — but not the Oscar, although he was nominated — for his portrayal of J.J. “Jake” Gittes, a private detective in Los Angeles in the 1930s. The film-noir feel of the flick, and the mystery surrounding the plot certainly make this one of Nicholson’s more interesting roles. The film’s significance as an American classic also helps keep Nicholson’s role fresh in mind.
4. About Schmidt
Nicholson took on a very uncharacteristic role in About Schmidt, as a retired actuary dealing with the — spoiler alert here — sudden death of his wife. Critics loved his subdued performance, however, and he was nominated for an Oscar for Best Actor. Film critic Roger Ebert noted in 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.”
3. A Few Good Men
Nicholson provided a great villainous performance as Col. Nathan Jessep, and his classic line, “You can’t handle the truth!” is one of the seminal moments in American motion picture history. He received an Academy Award nomination for Best Supporting Actor.
2. As Good As It Gets
Nicholson landed his second Best Actor Academy Award for his role as misanthropic novelist Melvin Udall. Despite being almost 60 years old at the time, Nicholson seemed perfectly cast as the romantic lead opposite the much younger Helen Hunt. His best performance in a comedy.
1. One Flew Over the Cuckoo’s Nest
Nicholson took home his first Academy Award for Best Actor for his portrayal of Randall McMurphy, who turns a mental health institution on its ears in an adaptation of the Ken Kesey novel. The film earned an Academy sweep of all five major awards, taking home best picture, best lead actor, best lead actress, director and screenplay. Although Nicholson had starred in several movies before this 1975 film, One Flew Over the Cuckoo’s Nest made him a superstar.