50. Drive Me Crazy (1999)
Director: John Schultz
Stars: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Mark Metcalf, Ali Larter
Lame Love Song: "I Want it That Way," The Backstreet Boys
Love Conquers: Vengeance against exes
Sabrina the Teenage Witch and the always engaging Vince from Entourage as high school soul mates? How could such a film go wrong? In any number of ways, it turns out.
This romcom flips the script established by films like She's All That, as this time she is the alpha female queen bee and he is the coffee shop dwelling misunderstood weirdo who needs a makeover. That's innovation for you, folks.
The film was originally titled Next to You, but was retitled to take advantage of the synergy that could be created with the Britney Spears song of the moment, Drive Me Crazy. It's awesome when individual pieces of art can work together across forms like that. Masterful.