Sean Penn Achieves Historic Third Oscar Win at 2026 Academy Awards

Sean Penn has made history by winning his third Oscar for Best Supporting Actor at the 2026 Academy Awards for his role in 'One Battle After Another.' Despite his absence from the ceremony, his achievement solidifies his status as one of Hollywood's most celebrated actors. This win adds to his previous accolades, including two Best Actor Oscars. Throughout his career, Penn has often skipped major award events, maintaining a unique presence in the industry. Discover more about his remarkable journey and the accolades he has received over the years.

By Narendra Chaudhary Mar 16, 2026, 07:07 IST

Sean Penn's Remarkable Oscar Achievement

At the 98th Academy Awards, actor Sean Penn reached a significant career milestone by winning the Oscar for Best Supporting Actor for his role in One Battle After Another. This victory makes him only the fourth male actor in Oscar history to achieve three Academy Awards. Interestingly, Penn was not present at the ceremony, and Kieran Culkin accepted the award on his behalf, humorously noting, “Sean Penn couldn’t be here this evening - or didn’t want to.”

This latest Oscar adds to Penn's previous wins for Best Actor for his performances in Milk and Mystic River, awarded in 2009 and 2004, respectively. Throughout his illustrious career, he has received numerous nominations at the Academy Awards.

Penn's portrayal of Colonel Steven J. Lockjaw in One Battle After Another, directed by Paul Thomas Anderson, has garnered widespread acclaim throughout the awards season. His performance has earned him multiple accolades, including wins at the BAFTA Awards and the Actor Awards. However, he chose to skip these ceremonies as well, continuing a trend of avoiding major award events.

Earlier this year, he made headlines at the Golden Globe Awards for briefly violating the venue's no-smoking policy by lighting a cigarette during the event. Despite the attention, he lost the Supporting Actor award that night to Stellan Skarsgård for Sentimental Value.

Despite being nominated five times prior to this win, Penn has often missed these ceremonies. In past interviews, he humorously suggested melting down his Oscars to create bullets for Ukraine amid the ongoing conflict. His nominations have included films such as Dead Man Walking, Sweet and Lowdown, and I Am Sam.