Sean Penn hasn’t spent much time at awards shows this awards season. Still, he has now joined an exclusive club as one of only four men to win three Oscars in competitive acting awards. Penn won Best Supporting Actor at the 98th Academy Awards for his role as the villain Col. Steven J. Lockjaw in One Battle After Another, coming out ahead of Delroy Lindo (who was CinemaBlend's pick to win), Stellan Skarsgard, Jacob Elordi, and his castmate, Benicio del Toro.
Now, 4 Men Have Won 3 Competitive Acting Awards
Penn previously won for Best Actor in 2004 for Mystic River and in 2009 for Milk. With his win for Best Supporting Actor, he has joined Jack Nicholson, Daniel Day-Lewis, and Walter Brennan in the three-timers club. Day-Lewis is the only actor to win Best Actor three times, winning for My Left Foot in 1990, There Will Be Blood in 2008 (also a movie directed by Paul Thomas Anderson), and Lincoln in 2013. Brennan won all three of his in the supporting category for movies in the 1930s. Like Penn, Nicholson has won Best Actor twice (for One Flew Over the Cuckoo’s Nest in 1976 and As Good As It Gets in 1998), and once for Best Supporting Oscar (for 1983’s Terms of Endearment).
The record for competitive Oscars is held by the legendary Katharine Hepburn, who won four Best Actress Oscars over her incredible career. Her first came in 1933 for Morning Glory, and her last came almost 50 years later for 1981’s On Golden Pond. In between, she won back-to-back Oscars for Guess Who's Coming to Dinner in 1967 and The Lion in Winter the following year. Ingrid Bergman, Meryl Streep, and Francis McDormand each have three as well. If you’re wondering who has won the most competitive Oscars overall, the answer is Walt Disney, who won 22 over his career. None in an acting category, of course.
Penn Was A No-Show
As he has been most of this awards season, Penn was a no-show at the Oscars, which is airing on ABC, and with a Hulu subscription, this year. This is his third big win in a row for the role, winning a BAFTA and an Actor Award for supporting actor in One Battle After Another, but he wasn’t at either of those awards shows, either. Weirdly, the only televised awards show that Penn did attend was the Golden Globes, where he lost to Jacob Elordi for his role as The Monster in Frankenstein.
It’s not all that surprising that Penn would skip the Oscars. He doesn’t seem to be in for the awards, or even enjoy acting sometimes, but this is the Oscars, after all. Kieran Culkin, last year’s winner in the same category, who presented it tonight, even commented on it, saying:
Sean Penn couldn’t be here tonight. Or didn’t want to. So I’ll be accepting the award on his behalf.
One would think that if there was going to be one ceremony to show up to, it would be this one. Alas, he wasn’t there. It’s actually kind of fitting for winning for a role like the villain Lockjaw.
