Michael B. Jordan and Sean Penn Lead a Night of Records at the 2026 Oscars

The 98th Academy Awards was dominated by two names above all others: Sean Penn and Michael B. Jordan. Penn made history by claiming his third Oscar — Best Supporting Actor for One Battle After Another — tying the all-time record for male acting wins. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio in one of the most anticipated contests of the night. Both men rewrote their respective legacies on the same evening.
Penn’s absence from the ceremony was a notable subplot. He did not attend the Dolby Theatre, leaving Kieran Culkin to accept on his behalf and offer a deadpan explanation for his non-appearance. Penn’s three Oscars now stand alongside those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the record holders Penn has now matched. His previous wins were for Mystic River and Milk.
In One Battle After Another, Penn plays a militaristic zealot with ferocious conviction. Paul Thomas Anderson’s direction gave the film a sharp comic edge that set it apart from conventional awards-season fare. Anderson himself was recognized twice — for Best Director and Best Adapted Screenplay — making it a career-high evening for one of American cinema’s most respected auteurs.
Conan O’Brien served as host and struck a balance between humor and sincerity throughout. His jokes about artificial intelligence were among the evening’s most quoted lines. He also took time to note that the nominee pool included participants from 31 countries and six continents, framing the ceremony as an increasingly global event.
DiCaprio’s loss in the Best Actor race was one of the evening’s more surprising results, given his widely praised performance. The 2026 Oscars were full of records broken, milestones reached, and one seat conspicuously empty — and that combination made for a truly memorable evening.