It’s not an exaggeration to suggest Sean Penn hasn’t been in the awards conversation in any capacity since 2009. That’s when he won his second Best Actor Oscar for portraying Harvey Milk in Gus Van Sant’s “Milk.” 17 years later, he’s joined the small club of actors who have won three Academy Awards. His third win came in the Supporting Actor category for his role inPaul Thomas Anderson’s “One Battle After Another.”
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For his role as Col. Steven J. Lockjaw, Penn also won the BAFTA Award and SAG Actor Award for Best Actor. He lost several other competitive prizes this season to his “One Battle” co-star, Benicio Del Toro.
Penn’s previous nominations were all in the Best Actor category for his performances in “Dead Man Walking” (1996),“Sweet and Lowdown” (2000), and “I Am Sam” (2002). He won his first Oscar for Clint Eastwood’s “Mystic River” in 2004.
Only seven other actors have won three more Oscars for acting. They include Meryl Streep, Daniel Day-Lewis, Frances McDormand, Jack Nicholson, Ingrid Bergman, and Walter Brennan. Katharine Hepburn holds the record with four wins. A record she set the year Penn first appeared in a major Hollywood production.
Over his illustrious 45-year career, Penn has won an Honorary Caesar Award, the Volpi Cup for Best Actor at the Venice Film Festival (1998’s “Hurlyburly”), two Independent Spirit Awards, Best Actor at the Cannes Film Festival (1997’s “She’s So Lovely”) and Best Actor at the Berlin Film Festival (“Dead Man Walking”). Notable credits include his breakthrough, “Fast Times at Ridgemont High,” “Taps,” “At Close Range,” “We’re No Angels,” “The Falcon and the Snowman,” “Carlito’s Way,” “Before Night Falls,” “The Thin Red Line,” “21 Grams,” “The Tree of Life,” and “Licorice Pizza,” among others. Overall, Penn has appeared in six Best Picture nominees.
He’s directed three films that screened at the Cannes Film Festival: “The Pledge,” “The Last Face,” and “Flag Day.” He also helmed “Into the Wild,” “The Indian Runner,” and the documentary, “Superpower.”
While not on hand to accept his awards at the BAFTAs or SAG Awards, Penn did pick up his Oscar at the Dolby Theater in person.
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