#6
The Philadelphia Story (1940)
The Philadelphia Story (1940) epitomizes screwball elegance, with Cary Grant, Katharine Hepburn, and James Stewart earning 6 Oscar nominations and 2 wins, including Stewart's only competitive Best Actor award. Hepburn personally purchased the play rights for $150,000 to revive her career after being labeled 'box office poison.' This gambit paid off: the film holds a 100% Rotten Tomatoes score from 60 reviews, one of the highest of any comedy on this list.
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