This person is the old drunkard Bobby Singer who occasionally appears in "Supernatural".
He guest-starred as John Franklin Fry in the second season of "Deadwood", as Dwight in "Mike & Molly", as Shelby Parlow in "Justified", as Lawson in "Breaking Bad", and played Charlie Mills in the mini-series "Harper's Island" and Whitney Ellsworth in "Deadwood".
He has made cameo appearances in many crime dramas and portrayed various minor roles in films, often as a police officer. For example, he played Duke Grover in "The Life of David Gale", Ranger Tony in "Adaptation.", Sheriff Ritter in "Joy Ride", and Detective Clarkson in "Sister Act". He portrayed Detective Earl Gaddis in the 13-episode TV series "Reasonable Doubts".
Cast director Cecily Adams was Jim's wife, who passed away in 2008. Her father was the star of "Get Smart", Maxwell Smart number 86! He also passed away in 2005.