Ranking The 25 Best Rom-Coms of All-Time

4. The Philadelphia Story (1940)

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The Philadelphia Story is one of those legendary Hollywood films — and not just because it stars Cary Grant, James Stewart, and Katharine Hepburn. Hepburn plays Tracy Lord, the eligible daughter of a well-off Philadelphia family due to marry. When Grant and Stewart’s characters fall for Tracy, chaos ensues. Possessing excellent casting, a great storyline, and a sharp script, The Philadelphia Story remains a classic of the genre, and one of Hepburn’s best role to date.