23. Clueless (1995)
California girl Cher Horowitz (Alicia Silverstone) is young, rich, beautiful, and looking to get her claws into Christian (Justin Walker), the new guy at school. Charmed by his regular onslaught of compliments on her sartorial choices, Cher puts on her sexiest dress and invites him over for a night of movie-watching (and then some).
But she quickly discovers that her friends were right when they told her that Christian is "a disco-dancing, Oscar Wilde-reading, Streisand ticket-holding friend of Dorothy." (Translation: He's gay.)