9. "Reality Bites"
Few movies are more quintessentially 1990s than Reality Bites. Stiller directed the 1994 film, which centers around a group of college graduates trying to find their place in the world as they deal with sexuality, AIDS, unemployment and the pressures of adulthood. The soundtrack included Lisa Loeb's "Stay (I Missed You)," which became a massive hit for the singer-songwriter, although she was an unknown, unsigned artist at the time. The film also brought the Knack's 1979 hit "My Sharona" back into the spotlight, and it helped make Stiller a major MTV player after the cancellation of The Ben Stiller Show the previous year.