Owen Benjamin produces the late show on Saturday Nights at The Improv in Hollywood, California, and he has also performed on MTV’s show Punk’d. He is a regular correspondent on The Jay Leno Show having appeared twice in a segment performing comical jingles for local Burbank businesses.
Benjamin has starred in several web-only video series. Since 2008 he has been appearing on Sony Pictures Television’s C-SPOT, including the role of Owen on Gaytown as well as hosting his own series, Owen Benjamin Presents. In March 2009 Benjamin began playing the role of Chance Stevens on Heckle U for CBS Interactive.
In 2007 Benjamin made an appearance in I Now Pronounce You Chuck and Larry. The scene was deleted from the theatrical release, but can be found in the extended deleted scenes in the home video release. In 2008 Benjamin had a supporting role in The House Bunny.
In 2009, he played the leading role in the romantic comedy All’s Faire in Love, costarring with Christina Ricci.
On July 19, 2012, Sullivan and Son premiered on TBS. Benjamin has a supporting role as Owen, Steve Sullivan’s childhood friend. In the episode “Creepy Love Songs”, Benjamin displayed his piano playing skill.
On Spike TV’s Bar Rescue S3E10 episode “Meat Sauna” Benjamin made a special appearance as he helps the dying Stand Up Scottsdale comedy club be rescued into being reopened as a franchise of the Laugh Factory Comedy Club. He gave his expertise to the club to help it, as well as performing his comedy act for their re-opening under the new name.