In 1999, 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 has since 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. Starr co-starred in the 2007 comedy film
Knocked Up, which was directed by Judd Apatow. The same year, he had small appearances in
Superbad and
Walk Hard: The Dewey Cox Story, both of which were produced by Apatow.
Knocked Up was critically praised and was successful at the box office. The success of
Knocked Up led to Starr having larger roles in films, such as
Good Dick and
Adventureland. Starr also appears in many well-received
short films that premiere at film festivals, such as the
Sundance Film Festival. In 2008, Starr played a minor role in
The Incredible Hulk. He reprised the role,
retroactively identified as
Roger Harrington, in
Spider-Man: Homecoming (2017),
Spider-Man: Far From Home (2019) and
Spider-Man: No Way Home (2021). From 2009 to 2010, Starr was a series regular portraying Roman DeBeers on the
Starz sitcom
Party Down. The series was cancelled after two seasons and there were discussions of adapting the series into film, but this never came to fruition. From 2011 to 2013, he co-starred on the
Adult Swim television series
NTSF:SD:SUV::, in which he played Sam Stern. In 2011, Starr had a major role in the film
A Good Old Fashioned Orgy and also had guest appearances on television series such as
Mad Love,
Community, and
Childrens Hospital. In the latter, he reprised his role of Roman DeBeers from
Party Down. Starr reunited with
Freaks and Geeks and
Party Down cast member
Lizzy Caplan in the 2012 film
Save the Date, which premiered at the Sundance Film Festival. In 2019,
Party Down's co-creator and producer Dan Etheridge announced plans for a reunion with the original cast (including Starr) during a discussion at Vulture Festival. The third season of the series premiered in February 2023. In 2022, he joined the cast for
Tulsa King, playing the role of Lawrence "Bodhi" Geigerman, the owner of a weed store. In 2025, Starr founded the candy company
Sweet Stash with
Adeev and Ezra Potash; the company produces
gummies in the shape of
musical notes. ==Filmography==