Best known for his role as Bobby Singer in the CW's thriller, Supernatural and previously on David Milch's HBO Western, Deadwood.
He has had recurring roles on other television series including Justified and Harper's Island.
He had one of his best-known film roles in Adaptation (2002) with Nicolas Cage.
He joined the U.S. Marine Corps after high school.
He was married to his second wife, Cecily Adams, from 1989 to 2004.