01/30/2014 AT 10:00 AM ET
Cue Sixpence None the Richer: She’s All That was released 15 years ago this week.
The story of a hunky high schooler attempting to woo a girl of the dorky, artistic persuasion as part of a jock bet, She’s All That inevitably ends – spoiler alert – with the girl transforming into a babe and the pair falling in love.
She’s All That also ushered in a monumental movie year for all those between the ages of 13 and 19. If you were looking for something to see on those awkward, braces-filled first dates, 1999 made it easier than ever before.
Along with She’s All That, these eight teen classics all hit theaters the same year.
Release Date: Jan. 15
Starring: James Van Der Beek, Jon Voight, Paul Walker, Ron Lester, Scott Caan
Release Date: Feb. 19
Starring: Rose McGowan, Rebecca Gayheart, Julie Benz, Judy Greer and Pam Grier
10 Things I Hate About You
Release Date: March 31
Starring: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Gabrielle Union
Never Been Kissed
Release Date: April 9
Starring: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, John C. Reilly
Release Date: July 9
Starring: Jason Biggs, Chris Klein, Alyson Hannigan, Shannon Elizabeth, Natasha Lyonne, Seann William Scott
Drop Dead Gorgeous
Drive Me Crazy
Release Date: Oct. 1
Starring: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Ali Larter
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