Aired: 1999-2000

Though the short-lived series premiered too early for its time, its unflinching chronicle of social awkwardness and the perils of puberty (starring a young James Franco and Linda Cardellini) encapsulated the ultimate high school experience. It's also the reason you've heard of Judd Apatow, Seth Rogen, Jason Segel, and Martin Starr.

Producers recruited Ben Stiller to make a cameo as a Secret Service agent to stave off network cancellation, but the episode aired after the series had already been cancelled.