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.

Before and after they were stars! Piper and the gang were incarcerated, they were your garden variety high school students, stand up comedians, 90s teen stars and makeover show hosts. See where the stars of Jenji Cohen’s critically acclaimed and addictive Orange is the New Black were before the cell block. Season Two starts on June 6th on Netflix.

Once there was a time when MILFs were just a weird combination of letters, and when the words “This one time, at band camp…” didn’t strike fear into the hearts of flautists everywhere. This was, of course, the murky time in our history known as BAP: Before American Pie. Then, in 1999, director brothers Paul and Chris Weitz decided to unleash the blockbuster American Pie into our consciousness. The story of four teenage boys who make a pact to lose their virginity by prom night soon became the Porky’s for a new generation. Now they’re back with American Reunion, where Jim, Michelle, Stifler, and the gang have returned for a new assault against warm baked goods and our sense of well-being. See what the American Pie cast really looked like in high school, and find out what they’re up to today.

As we celebrate Chuck Norris’ birthday take a look at other celebrities who have played themselves on TV and film.