With a part in the independent short "Allerd Fishbein's in Love" to his credit, Daley got his big break in 1999, making his TV debut with a regular starring turn on the NBC comedy-drama "Freaks and Geeks". He played Sam, a physically and emotionally immature high school freshman obsessed with "Star Wars", the role-playing game Dungeons & Dragons and Steve Martin movies. A remarkably (and often painfully) realistic portrait of high school life, "Freaks and Geeks" won critical acclaim and a cult following, but didn't bring in enough viewers to please the network. Despite it's quick demise, the series offered Daley a unique opportunity to showcase his abilities, and the controversial cancellation resulted in high profile press that the young actor may not have gotten otherwise. The following season Daley was cast in another TV series, ABC's "The Geena Davis Show". Here he portrayed Carter, the unpredictable teenage son of a political writer (Peter Horton) set to marry the titular actress' New York career woman.