Jack Nicholson hasn’t appeared in a movie since 2010’s How Do You Know, but the now 88-year-old has more than earned his retirement because he’s one of the greatest and most famous actors of all time. The legendary actor starred in classic films like Easy Rider, The Shining, A Few Good Men, and countless more, while also winning three Oscars and six Golden Globes for his talent.
We can argue about which of his movies is the best all day long, but what is factual is that only three of Nicholson’s movies actually won the Academy Award for Best Picture. Still, which one comes out as the greatest? This list will rank all three of Jack Nicholson’s Best Picture-winning movies based on their overall quality, impact and legacy on cinema, and their overall reputation among the 97 movies that have won the award over the Academy’s long history.
3
‘Terms of Endearment’ (1983)
Terms of Endearment is adapted from Larry McMurty‘s 1975 novel of the same. The film was written and directed by James L. Brooks, who later worked with Nicholson on As Good as It Gets (for which Jack won an Oscar) and How Do You Know. Starring Debra Winger, Shirley MacLaine, Danny DeVito, and John Lithgow, Terms of Endearment is one of cinema’s most heartbreaking tearjerkers. MacLaine plays a widow named Aurora Greenway, with Nicholson in a supporting role as Garrett Breedlove, the neighbor she starts a romance with. This movie belongs to MacLaine and Winger, though, with a devastating ending that rivals any of the saddest finales ever put on film.
Nicholson wasn’t the lead, but he did win a Best Supporting Actor Oscar (John Lithgow was nominated in the same category). In his perfect four-star written review, Roger Ebert wrote, “This is a wonderful film. There isn’t a thing that I would change, and I was exhilarated by the freedom it gives itself to move from the high comedy of Nicholson’s best moments to the acting of Debra Winger in the closing scenes.” Terms of Endearment won five Academy Awards overall, including James L. Brooks for Best Director and Best Adapted Screenplay, Shirley MacLaine for Best Actress (Debra Winger was nominated too), and Best Picture, beating the likes of The Big Chill, The Dresser, The Right Stuff, and Tender Mercies. Terms of Endearment was a huge box office success as well, making over $108 million on an $8 million budget.
2
‘One Flew Over the Cuckoo’s Nest’ (1975)
Eight years before Terms of Endearment was One Flew Over the Cuckoo’s Nest, again adapted from a novel, this time in 1962 by Ken Kesey. The film was co-written by Lawrence Hauben and Bo Goldman, and directed by Miloš Forman (Amadeus, The People vs. Larry Flynt). Jack Nicholson is the lead, but with a stellar supporting cast made up of Louise Fletcher as the terrifying and iconic Nurse Ratched, and future big names Brad Dourif, Christopher Lloyd, and again with Nicholson, Danny DeVito. Jack plays Randle McMurphy, an inmate who pretends to be criminally insane so he can get himself moved to a mental institution. There, he meets a variety of characters who may come off as crazy on the outside, but who are mostly good and misunderstood souls who will challenge Randle’s way of thinking. Just like Terms of Endearment, One Flew Over the Cuckoo’s Nest has an utterly devastating third act you’ll never be able to forget.
Nicholson won the Best Actor Oscar (his first) for his performance. Newsweek raved about his turn as Randle McMurphy, saying that he was born to play the role and, “In a way McMurphy is the ultimate Jack Nicholson performance — the last angry crazy profane wise-guy rebel, blowing himself up in the schrapnel of his own bleeding laughter.” The movie was nominated for nine Oscars, and won the Big Five: Forman as Best Director, Fletcher as Best Actress, and Hauben and Goldman for Best Adapted Screenplay. One Flew Over the Cuckoo’s Nest also beat out Dog Day Afternoon, Barry Lyndon, Nashville, and the biggest hit of the year (and then all-time), Jaws, to win Best Picture. Although it couldn’t match Jaws‘ phenomenal box office haul, One Flew Over the Cuckoo’s Nest still pulled in an impressive $109 million on a meager $3 million budget.
1
‘The Departed’ (2006)
You could have picked Terms of Endearment or One Flew Over the Cuckoo’s Nest as the best Jack Nicholson Best Picture winner, and you wouldn’t be wrong, but we’re going to go with The Departed. It not only gives us one of Nicholson’s best and scariest performances, but it also did wonders for Martin Scorsese’s career. Firstly, The Departed is the epitome of cool, tragic, and action-packed. Instead of being based on a novel, The Departed is a reimagining of the 2002 Hong Kong film Internal Affairs. Written by William Monahan and directed by Scorsese, the king of violent crime movies, The Departed is overflowing with A-listers such as Leonardo DiCaprio, Matt Damon, Martin Sheen, and Alec Baldwin. Nicholson is at the center of the drama as Boston mob boss Frank Costello, who has planted one of his men (Damon) in the police department, not knowing that they have also infiltrated Costello’s gang with a cop (DiCaprio). What follows is a tense masterpiece with a shocking ending that’ll make you jump out of your seat.
Nicholson was nominated for a Golden Globe but shut out of a crowded Oscars race. Mark Wahlberg was nominated in a supporting role instead, but lost out to Alan Arkin for Little Miss Sunshine. This doesn’t mean, however, that The Departed isn’t one of Nicholson’s best roles. Somehow, this was the first time that Nicholson and Scorsese worked together, but the acting icon jumps off the screen with his energy, with Roger Ebert writing in his four-star review, “He has a moment and a line in this movie that stands beside Joe Pesci’s work at a similar moment in Goodfellas.”
Despite not being a sequel, superhero movie, or family film, The Departed still drew a huge audience to the theater, making almost $300 million worldwide! It wasn’t just moviegoers who noticed either, but critics and award voters as well. At the 2007 Academy Awards, The Departed was nominated for five Oscars. It won for Best Film Editing, Best Adapted Screenplay Writing, and it was recognized as the Best Picture of the year over Babel, Letters From Iwo Jima, Little Miss Sunshine, and The Queen. What puts it over the top is that, finally, after decades of losing, Martin Scorsese scored his first Oscar for Best Director. That doesn’t happen without Jack Nicholson.