Stamatopoulos was hired on
The Ben Stiller Show after
Andy Dick convinced him to submit a spec script for a
Simpsons episode. There, he met and worked with
Bob Odenkirk. After Stiller's show was canceled, he moved to New York City, where he wrote during the 1990s for
The Dana Carvey Show, ''
Late Night with Conan O'Brien (also with Odenkirk), Late Show with David Letterman, and Mr. Show with Bob and David''. In 2000, Stamatopoulos and
Robert Smigel pitched Comedy Central a spin-off of Smigel's
TV Funhouse cartoons (which were appearing singly as animated shorts on
Saturday Night Live episodes) as a half-hour sketch comedy show. The standalone
TV Funhouse show premiered in 2000 but was canceled after one season. He later joined the writing staff on
Mad TV. Stamatopoulos worked as a creative consultant and contributing writer on the first season of
Tom Goes to the Mayor, with
Tim & Eric and Bob Odenkirk. He also provided the voice of Drinky Crow on
The Drinky Crow Show, which aired for one season on
Adult Swim. His
stop motion animated series
Moral Orel premiered on Adult Swim on Christmas 2005 and aired for three seasons, airing its final episode in December 2008; a follow-up special aired in 2012. Following
Moral Orel, Stamatopoulos created ''
Mary Shelley's Frankenhole'', a
stop motion series, for Adult Swim. It ran for two seasons from 2010 to 2012. Stamatopoulos was a writer, consulting writer, producer and actor on the 2009 NBC sitcom
Community. He wrote two animated episodes for the series, "
Abed's Uncontrollable Christmas" (2010) and "
G.I. Jeff" (2014). He played the recurring role of Alex "
Star-Burns" Osbourne, a character whose nickname derived from his large star-shaped
sideburns. Together with
Community creator
Dan Harmon, Stamatopoulos started production company
Starburns Industries. A long-time fan of radio personality
Steve Dahl, Stamatopoulos hosted a podcast,
Sorry About Everything, from May 2012 until June 2013 on Dahl's
Steve Dahl Network. Stamatopoulos and friend Andy Dick hosted a weekly podcast, ''Dino and Andy's Skull Juice
, which premiered in late 2016 and was initially produced by Feral Audio. Due to an on-air incident of hostility in mid-2018, Dick was asked to leave the podcast. Stamatopoulos asked friend and recurring guest Dana Snyder to replace Dick as co-host, and the podcast was renamed Dino & Dana's Safe Space''. Additional co-hosts Laetitia "Tish" Burns and
Spencer Crittenden were also given billing in the podcast. ==Personal life==