The Only Actors To Win Three Or More Oscars – SlashFilm

The list of Best Supporting Actor nominations at the 98th Academy Awards was one of the most stacked categories of the night, from Delroy Lindo in “Sinners” to Benicio del Toro’s scene-stealing performance as Sensei Sergio in “One Battle After Another.” But the win has officially gone to del Toro’s co-star Sean Penn for his performance as the evil Colonel Steven Lockjaw. We at /Film consider Colonel Lockjaw one of the greatest movie villains of 2025 — he’s a buffoon but also a genuinely dangerous white supremacist — and it appears the Academy agreed.

This marks Penn’s third Oscar win; he previously won Best Actor for “Mystic River” in 2004, where he played Jimmy Markum (a former Boston gangster and grieving father of a murdered girl) and then Best Actor again in 2009 for “Milk” (as Harvey Milk, the openly gay mayor of San Francisco who was assassinated in 1978).

Prior to his “Mystic River” win, Penn had been nominated for Best Actor three times: in 1996 for “Dead Man Walking” (as Matthew Poncelet, a man sentenced to death row), in 2000 for “Sweet and Lowdown” (as jazz musician Emmet Ray), and then in 2002 for “I Am Sam” (as Sam Dawson, an intellectually disabled single father).

His win for “One Battle After Another” puts Penn in a rather exclusive club of people who have won three or more Oscars for acting. Who are the others?

The first ever actor to win three acting Oscars was Walter Brennan, who won Best Supporting Actor three times during the early years of the awards ceremonies. In 1937, during the ninth ever Academy Awards, Brennan won the first ever Best Supporting Actor award for the lumberjack drama “Come and Get It.” Two years later, he won again for playing Peter Goodwin in “Kentucky,” a drama about horse racing and two feuding families.

Brennan’s third and final Best Supporting Actor win came in 1941 for “The Westerner.” Brennan played Judge Roy Bean, the real-life saloon owner and judge in 19th century Val Verde County, Texas. Brennan’s Judge Bean is the villain of the film, opposite Gary Cooper as the cowboy Cole Harden.

Brennan received his fourth Best Supporting Actor nomination in 1942 for another Gary Cooper picture: “Sergeant York,” though this time he did not win. (Donald Crisp won for John Ford’s “How Green Was My Valley,” which also won Best Picture and Best Director, and the first ever 20th Century Fox film to win Best Picture.)

The current record for most Oscar acting wins is Katharine Hepburn, queen of old Hollywood. She won Best Actress four times, first in 1934 for her third ever film, “Morning Glory” (as struggling actress Eva Lovelace). It took a while for the Academy to show Hepburn love again; between this and 1968, she was nominated for Best Actress eight times, but never won.

She finally won Best Actress again in back to back years in 1968 and 1969: first for social drama “Guess Who’s Coming to Dinner” (as the mother of a young white woman marrying a Black man) and then for period piece “The Lion in Winter” as Eleanor of Aquitaine, queen of King Henry II (Peter O’Toole). Hepburn prevailed again in her last Best Actress nomination, in 1981 for “On Golden Pond,” as one half of the elderly Thayer couple (Hepburn played the wife Ethel, opposite Henry Fonda as her husband Norman).

Notably, despite her four Oscar wins, Hepburn never actually showed up to the ceremony to collect her prizes; she claimed that her prize was her work itself. Sean Penn not showing up to the 98th Oscars is thus him carrying on the tradition of Katharine Hepburn.

After Katharine Hepburn, the second actress to become a three-time Oscar winner was Ingrid Bergman. Like Hepburn, her wins were spread across decades.

Bergman was originally nominated for Best Actress in 1944 as Maria in “For Whom the Bell Tolls,” but she didn’t win until the following year for “Gaslight.” That movie, the origin of the psychological term “gaslighting,” was a thriller starring Bergman as Paula Anton, a woman whose husband is trying to drive her insane.

Bergman was next nominated for Best Actress in 1946 for the Bing Crosby vehicle “The Bells of St. Mary’s” as the nun Sister Mary Benedict, and then in 1949 for “Joan of Arc.” She finally won a second Best Actress award in 1957 for “Anastasia,” inspired by the story of Anna Anderson who claimed to be the murdered Russian Grand Duchess Anastasia Nikolaevna.

Bergman’s third Oscar win was in Best Supporting Actress for the 1974 “Murder on the Orient Express,” directed by Sidney Lumet. Bergman played Swedish missionary Greta Ohlsson, one of the mystery’s 12 murder suspects. In 1979, Bergman got another nomination as Best Actress for Ingmar Bergman’s (no relation) “Autumn Sonata.”

Meryl Streep is one of the best actors ever, and it’s reflected in the number of Oscars she’s either won or been considered for. As of this writing, Streep holds the Guinness World Record for the most Oscar nominations in history with 21. That’s pretty incredible, but which three roles did she win the awards for?

Streep first tasted Oscar glory at the 52nd Academy Awards, winning Best Supporting Actress for “Kramer vs. Kramer.” Regarded as one of the best movies about divorce ever, Streep’s character finds herself locked in a custody battle with her husband (played by Dustin Hoffman), resulting in a court battle.

Of course, divorce and custody battles are light-hearted topics compared to the movie that earned Streep her first Best Actress in a Leading Role win. In “Sophie’s Choice,” she plays a mother who must choose which child gets to live during the Holocaust — or else they will both be killed. Streep even learned Polish to prepare for the role of Sophie,, and this tendency to chase authenticity is why she is a record-breaking Oscar-nominee.

Following that, Streep won Best Actress for “The Iron Lady in 2012.” This one sees her play former British Prime Minister Margaret Thatcher, and critics and viewers agreed that Streep’s performance is incredible and layered following the film’s release. (Kieran Fisher)

Jack Nicholson has been nominated as Best Actor and Best Supporting Actor 12 times total, but he’s only won three. Following a 1970 nomination as Best Supporting Actor for “Easy Rider,” he was nominated as Best Actor several times over: in 1971 for “For Five Easy Pieces,” in 1974 for “The Last Detail,” and in 1975 for “Chinatown.” In 1976, for his third nomination in a year, the Academy finally stopped taking Nicholson for granted and he won Best Actor for playing R.P. McMurphy in “One Flew Over the Cuckoo’s Nest.” McMurphy, a convict who fakes mental illness to get out of forced labor, bites off more than he can chew.

Nicholson was subsequently nominated, again, for Best Supporting Actor in 1982 for Russian Revolution drama “Reds,” and then he won the award in 1984 for “Terms of Endearment” as the former astronaut Garrett Breedlove.

Two more Best Actor nominations for Nicholson — 1985 crime comedy “Prizzi’s Honor” and 1987 Great Depression drama “Ironweed” — came up empty, as did a Best Supporting Actor nomination for Colonel Nathan Jessup in Navy courtroom drama “A Few Good Men.” Nicholson once more prevailed as Best Actor in 1998 for “As Good as It Gets,” where he played cynical author Melvin Udall. He was nominated as Best Actor once more in 2003 for “About Schmidt,” as depressed retiree Warren Schmidt.

Nicholson himself is currently retired from acting, but three Oscar wins is just one part of an incredible legacy he built while working.

If there’s a go-to answer for “best actor alive,” then the semi-retired Daniel Day-Lewis is that answer for many people. The British actor is well-known for his intense, research-heavy method of performance, but no one can argue with the results. The Academy certainly hasn’t, given that he’s been nominated for Best Actor six times and won three.

His first nomination and win was in 1990 for “My Left Foot,” a biopic of Christy Brown, an Irish man born with cerebral palsy. Day-Lewis was subsequently nominated in 1994 for “In the Name of the Father” — where he played Gerry Conlon, one of the “Guildford Four,” Irish people wrongly convicted of a 1974 bombing of England’s Guildford pub. About a decade later in 2003, he was nominated again for playing Bill “The Butcher” Cutting in Martin Scorsese’s “Gangs of New York,” a bombastic, nationalistic gang leader in 19th century New York.

Day-Lewis finally won a second Best Actor award for playing oil baron Daniel Plainview in Paul Thomas Anderson’s “There Will Be Blood,” and then again in 2013 for Steven Spielberg’s “Lincoln,” where he played the eponymous 16th U.S. President at the tail end of the U.S. Civil War. Day-Lewis worked with Anderson again on 2017 romantic black comedy “Phantom Thread” and earned a sixth Best Actor nomination for playing uptight dressmaker Reynolds Woodcock.

You can always rely on Frances McDormand to deliver great performances. Even though she’s won three Oscars, some fans might argue that she deserves more. Be that as it may, bagging three Academy Awards is no small feat, but McDormand deserved all of them.

McDormand’s first win came at the 69th Academy Awards, where she took home the Best Actress in a Leading Role trophy for her performance in the real-life-inspired (sort of) “Fargo.” The Coen Brothers’ crime-comedy sees her play a pregnant police officer tasked with investigating a kidnapping that goes wrong, leading to all kinds of madness.

The “Fargo” star’s second win arrived at the 2018 ceremony for her performance for her outing in “Three Billboards Outside Ebbing, Missouri.” Similar to “Fargo,” Martin McDonagh’s film is a dark comedy set in a small town, only this one tells the story of McDormand’s character trying to get justice for her daughter’s murder.

Of course, there’s more to McDormand’s career than projects about darkness in small towns. “Nomadland” centers around a woman who hits the road to try and make a living, and McDormand’s layered performance led to another Best Actress win at the 2021 Oscars ceremony. Don’t be surprised if there are more Oscars in this star’s future. (Kieran Fisher)