Then: With the possible exception of Singles, no movie is more 1990s than Reality Bites. The soundtrack featured the song "(Stay) I Missed You" by then-unsigned act Lisa Loeb and Nine Stories. Loeb lived near Ethan Hawke in New York, and they become friends around the time he was filming Reality Bites. He put the song on the soundtrack and it shot to Number One on the Hot 100, a first for an unsigned artist in the history of the chart. Hawke filmed a video for the song in a single take. Vh1 showed it more than a few times, turning Loeb's cat eye glasses into a huge fashion statement.
Now: Contrary to popular belief, Loeb isn't a One-Hit Wonder. She had a Top 20 hit in 1995 with "Do You Sleep," and two years later "I Do" reached Number 17. Her career hit a slump after that, but Loeb remained in the spotlight. She dated Dweezil Zappa, and even starred with him in the Food Network reality show Dweezil and Lisa. When the two split up, Lisa got her own reality show Number One Single in which she looked for love on her own. She released a new album earlier this year, and she continues to stay busy with voice-over work. She also had a hysterical cameo on the series finale of Gossip Girl where she wound up marrying (fictional) Nineties rocker Rufus Humphrey.