17. Clueless (1995)

A style-forward remake of a rom-com, Clueless is a modern retelling of Jane Austen's Emma. Alicia Silverstone's Cher is the '90s' ultimate icon—rich, fashionable, and happy to play cupid at a moment's notice. But when her own love becomes complicated, she realizes she's been "totally clueless" about what matters. With forever-quotable lines, a killer soundtrack, and Paul Rudd in his forever young prime, Clueless is one of the most beloved rom-coms ever produced. It's light, effortless, and proof that even the most together people can still mess up love along the way.
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Edited by Zainab Shaikh