She returned to films with a memorable supporting role in the Spencer Tracy-Katharine Hepburn comedy, "Adam's Rib" (1949), then vaulted to stardom the following year when she recreated her stage triumph of "Born Yesterday" in George Cukor's film adaptation. As the airheaded mistress of a shady and rather dull-witted tycoon who turns the tables on him once she's educated, Holliday won an Oscar as Best Actress of 1950 (beating out Gloria Swanson in "Sunset Boulevard" and Bette Davis and Anne Baxter in "All About Eve").
For the rest of the 50s, signed with Columbia, Holliday made a handful of films, delighting audiences as ditzy but surprisingly shrewd types in "The Marrying Kind" (1952), the delightful media satire "It Should Happen to You" and "Phfft!" (both 1953), "The Solid Gold Cadillac" and "Full of Life" (both 1956). Holliday's last film was recreating her stage role in the musical "Bells Are Ringing" (1960). She returned to the stage in the straight play "Laurette" (Taylor) and the musical "Hot Spot" (1952). A heavy smoker, Holliday died of throat cancer in 1965 at the age of 43.