Starr was cast as Bill Haverchuck in the NBC sitcom "Freaks and Geeks". The series received positive reviews from critics, but it suffered from low ratings and was canceled after only one season. It gained a strong cult following. Starr then had a number of guest appearances and one-time roles on shows such as "Ed", "Mysterious Ways", "Providence", "King of the Hill", and "Normal, Ohio". He had a small recurring role during the third season of "Roswell" as the character Monk. In 2002, Starr appeared in the films "Stealing Harvard" and "Cheats". He reunited with both "Freaks and Geeks" producer Judd Apatow and "Freaks and Geeks" co-star Seth Rogen when he made a guest appearance on Apatow's situational comedy "Undeclared" in the episode "The Perfect Date". In 2005, he appeared in the miniseries "Revelations" and the CBS sitcom "How I Met Your Mother".