1999 was THE year for teen movies: American Pie, She’s All That, 10 Things I Hate About You, Cruel Intentions, Varsity Blues, Jawbreaker and Dick were just a few of the releases. Now, they are all celebrating their 15th anniversaries. We’ve gone back to pick some of our favorite teen duos from the era. Trust us, it wasn’t easy.

We loved her as Jen, the intriguing new girl with the troubled past on Dawson’s Creek. And we fell in love with her all over again as she blossomed in movies like Dick and then more grown-up fare like Brokeback Mountain. And she’s taken on one of the great American icons in My Week with Marilyn. What’s not to love?