17. Katharine Hepburn, ‘The Philadelphia Story’ (1940)
George Cukor’s screwball comedy centers on a Philadelphia socialite who, on the eve of her wedding to a nouveau riche man, finds herself torn between him, her caddish ex-husband (Cary Grant), and a reporter dispatched to cover the nuptials (Jimmy Stewart). It’s regarded as one of the greatest screwballs of all time, and Hepburn owns the film. Despite this, and the fact that she was a previous winner, Hepburn lost the Best Actress Oscar to Ginger Rogers for her turn as a saleswoman torn between two men in Kitty Foyle, and is evidence of the Academy’s longstanding bias against great comedy performances. And the film that is, in this writer’s opinion, the best screwball comedy of all time, His Girl Friday, was also released in 1940, also co-starred Cary Grant, and received a staggering zero Oscar nominations.