#17: Ray Milland and Olivia de Havilland (1947)

In a full-circle Oscar moment, Ray Milland returned to the stage in 1947 to present Olivia de Havilland with the Best Actress award for To Each His Own. Her performance as a woman navigating love, loss, and sacrifice in wartime America earned her the first of two career Oscars.

This win was especially significant, as it marked de Havilland’s triumph after breaking free from restrictive studio contracts—a battle that reshaped Hollywood’s power dynamics. With this award, she cemented her reputation as one of the era’s most talented and determined actresses.