Leonardo DiCaprio Loses, Sean Penn Stays Home, and Michael B. Jordan Makes History

The 98th Academy Awards produced a trio of headline stories that will be discussed for years. Sean Penn won Best Supporting Actor for One Battle After Another — his third Oscar, tying the all-time male record — without attending the Dolby Theatre. Michael B. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio in one of the evening’s most anticipated contests. And Paul Thomas Anderson won his first-ever Oscars for directing and writing the same film that brought Penn his latest honor.

Penn’s absence was addressed by presenter Kieran Culkin, who collected the award and offered a wry line about the winner’s non-appearance. Penn’s three wins now match those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the previous record holders. Penn’s victories span 22 years and two acting categories, making his achievement particularly rich in context and complexity.

One Battle After Another, the film behind Penn’s win, featured Penn as a militaristic officer driven to extremes by conviction. Critics praised the performance as one of the year’s finest. Anderson’s double win — Adapted Screenplay and Best Director — confirmed a night of complete triumph for the production, with wins across the evening’s most prestigious categories.

Host Conan O’Brien was well-calibrated throughout the ceremony, delivering humor while acknowledging the weight of the occasion. He joked about artificial intelligence replacing human hosts and spoke movingly about the international diversity of the nominees, drawn from 31 nations across six continents. His opening set an optimistic and thoughtful tone for the evening.

Jordan’s win for Sinners was greeted with tremendous enthusiasm and confirmed his status as one of Hollywood’s most compelling leading men. The 2026 Oscars produced three separate stories that each deserved the front page — and all three got it.