The late '90s were all about teens. As millennials learned to drive, they began shaping pop culture. We even created a magazine for them. On the cover of TEEN PEOPLE's June/July 1999 issue: Julia Stiles, Brandy, and 19 other It Boys and It Girls — all under 21. Julia talks to us about 10 Things I Hate About You, Heath Ledger, and whether or not she dated Joseph Gordon-Levitt in her college years. Then, we test her 90s pop knowledge and find out Julia is more Ani DiFranco than Joey Tribbiani. Oh, and remember The Tom Green Show? Learn more about your ad choices. Visit megaphone.fm/adchoices