Sean Penn Wins Best Supporting Actor Oscar for ‘One Battle After Another’

Penn joins a rarified group of three-time acting Oscar winners that includes Meryl Streep, Jack Nicholson, and Daniel Day-Lewis.

Sean Penn has joined one of the most rarified groups in Hollywood history: the three-time acting Oscar winners. Penn has won Best Supporting Actor for his performance in “One Battle After Another” at the 98th Academy Awards, placing him among a group that includes Meryl Streep, Jack Nicholson, and Daniel Day-Lewis.

Penn did not attend the ceremony, with presenter Kieran Culkin saying “Sean Penn couldn’t be here tonight, or didn’t want to,” and accepting the award on Penn’s behalf.

As the white supremacist and wannabe Christmas Adventurer Col. Steven Lockjaw, Penn provided the ultimate antagonist for Anderson’s father-daughter story. His vile physicality and blithering insecurity blurred the line between true evil and Pynchonesque absurdity, perfectly connecting the two extremes in Paul Thomas Anderson’s politically charged blockbuster.

The character was loosely based on Brock Vond from Thomas Pynchon’s “Vineland,” though Anderson changed the names and modernized the setting to put his own spin on the source material.

While this is Penn’s first win in the supporting category, he previously took home Best Actor in 2004 and 2009 for his performances in Clint Eastwood’s “Mystic River” and Gus van Sant’s “Milk.” The former saw him play an ex-con who teams up with a childhood friend who became a detective to investigate the murder of his daughter. In the latter, he played famed LGBTQ activist Harvey Milk, who became the first openly gay man to hold public office in California.

Before winning, Penn also received three previous nominations in the category for his performances in “Dead Man Walking,” “I Am Sam,” and “Sweet and Lowdown.”

Penn is now the eighth actor to win three Oscars as a performer. Walter Brennan won for “Come and Get It,” “Kentucky,” and “The Westerner;” Ingrid Bergman won for “Gaslight,” “Anastasia,” and “Murder on the Orient Express;” Frances McDormand was honored for “Fargo,” “Three Billboards Outside Ebbing, Missouri,” and “Nomadland;” Day-Lewis has wins for “My Left Foot,” “There Will Be Blood” (also written and directed by Anderson), and “Lincoln;” Nicholson won for “One Flew Over the Cuckoo’s Nest,” “Terms of Endearment,” and “As Good as It Gets;” and Streep took home Oscars for “Kramer vs. Kramer,” “Sophie’s Choice,” and “The Iron Lady.”

But the ultimate title for most acting Oscar victories still belongs to Katharine Hepburn, who won four statues for “Morning Glory,” “Guess Who’s Coming to Dinner,” “The Lion in Winter,” and “On Golden Pond.” 

The 98th Academy Awards took place at the Dolby Theatre on Sunday, March 15, with Conan O’Brien returning as host. The ceremony was broadcast live on ABC starting at 8 p.m. ET/5 p.m. PT. Check out the full list of winners right here.