- Was David Letterman's first sidekick.
- Father of Rufus Wainwright and Martha Wainwright (by Kate McGarrigle), Lucy Wainwright (by Suzzy Roche) and Alexandra (by Ritamarie Kelly). Ex-brother-in-law of Jane McGarrigle and Anna McGarrigle. Son Rufus Wainwright wrote a song about an argument he once had with his father; it was entitled "Dinner At Eight".
- Played guitar and sang on three episodes of the third season of M*A*S*H (1972) as "Capt. Spalding". Songs included "North Korea Blues (Oh, Tokyo)", featured prominently throughout the episode "Rainbow Bridge". In 2004, he played one of the Cocoanut Grove singers (lead singer in tune "Happy Feet") in the Leonardo DiCaprio film The Aviator (2004), which also starred M*A*S*H (1972) alum Alan Alda. Wainwright's two children played the other lead singers (of different eras) in The Aviator (2004).
- Went to the same prep school that was featured in Dead Poets Society (1989).
- Was the resident singer when he appeared with Jasper Carrott in Carrott's UK show, Carrott Confidential (1987), in the late 80s. It was the first time he was seen by a British audience on TV.
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