Brian Truitt,Kim Willis March 6, 2026, 3:51 p.m. ET A look at the biggest Oscar winners, the 96 movies awarded best picture. 1927/28: "Wings" | Richard Arlen, Clara Bow and Charles "Buddy" Rogers star in the first Academy Award best-picture winner, a silent film. Sunset Boulevard, Corbis Via Getty Images 1928/29: "The Broadway Melody" | Bessie Love and Charles King star in the musical that was the first sound film to win.