Conan O’Brien Hosts, Sean Penn Stays Home, and Oscar History Is Made

The 98th Academy Awards brought together Hollywood’s finest at the Dolby Theatre — except for one of the night’s most celebrated winners. Sean Penn, honored with the Best Supporting Actor prize for One Battle After Another, was absent when his name was called, leaving presenter Kieran Culkin to step forward and collect the award. Culkin’s amused remark about Penn’s absence got a laugh out of the crowd before the evening moved on.

Penn’s win was his third Oscar, a figure that now puts him in the record books alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. All four men have claimed precisely three acting Oscars throughout their careers, the highest total ever reached by a male actor. Penn’s previous wins were both in the Best Actor category for his performances in Mystic River and Milk.

The film at the center of Penn’s historic win, One Battle After Another, is a gripping and darkly comic thriller directed by Paul Thomas Anderson. Penn plays a military officer of extreme conviction in the film, bringing an intensity that critics described as electrifying. Anderson had a career-high evening, winning both Adapted Screenplay and Best Director in what many called a long-overdue recognition.

Conan O’Brien delivered a warm and sharp-witted performance as host, drawing early laughs with a self-deprecating joke about the rise of AI-powered entertainment. He spoke about the power of film to transcend borders and bring people together, citing the 31 countries represented among the nominees. His tone was both funny and sincere in equal measure.

Michael B. Jordan triumphed in the Best Actor category over Leonardo DiCaprio, winning for his remarkable twin performance in Sinners. The 2026 Oscars delivered history, humor, and heart in equal measure — with Penn’s conspicuous absence adding a perfectly unconventional touch.