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He is best known for his work on the sitcom Friends for which he was nominated for a Primetime Emmy in 1999. In 2002, Calhoun along with Dan Schneider created the series What I Like About You starring Amanda Bynes and Jennie Garth. His other television credits include Jesse, Sons & Daughters, Caroline in the City, Kath & Kim and Gary Unmarried.
In 1990, he guest starred twice on the action series MacGyver, before pursuing a career behind the camera. He is still currently best friends with the actor who played "Angus MacGyver."