20+ Must-See Romantic Comedy Films of All Time

Published on 05/24/2023
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When Harry Met Sally

Is it possible to have truly platonic friendships between men and women? When Harry Met Sally, possibly Nora Ephron’s most successful film, tries to answer that question by following Harry (Billy Crystal) and Sally’s (Meg Ryan) friendship over a twelve-year period. Despite their initial disagreements as recent college graduates, Harry and Sally continue to meet paths over the next decade, eventually becoming good friends.

When Harry Met Sally

When Harry Met Sally

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Pretty Woman

The presence of Pretty Woman on this list almost doesn’t need to be explained. Both moviegoers and reviewers have firmly established this film as rom-com gold, and it will be remembered as the gold standard of what a romantic comedy can be. Julia Roberts plays Vivian, a Hollywood prostitute who meets Richard Genre’s Edward, a wealthy and emotionally closed-off businessman in desperate need of Beverly Hills instructions. After Vivian’s suggestion convinces Edward to bring her inside, they strike a deal: she will be his pretend girlfriend for the next six days at important business meetings in exchange for $3,000 and a new wardrobe. Of course, their false romance elicits genuine feelings, and the audience witnesses the two fall in love.

Pretty Woman

Pretty Woman

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