A fan of the film Grey Gardens (1975), he wrote a song with the same name for his second album, Poses. The song features an audio clip of 'Edith 'Little Edie' Bouvier Beale', taken from the film.
Performed songs featured in the soundtracks for The Myth of Fingerprints (1997) and Big Daddy (1999).
Named "Best New Artist" by "Rolling Stone" magazine in 1999.
Won a Juno Award for "Best Alternative Album" in 1999 and 2002.
Performed the song "Complainte de la Butte" for the film Moulin Rouge! (2001), the only song in French featured in the Paris-set movie.
I Eat Dinner (When the Hunger's Gone), the song he sings in Bridget Jones: The Edge of Reason (2004), was written by his mother, Kate McGarrigle.
His character Jeremy in Heights (2005) was based on himself.
Longtime companion has been Jorn Weissbrodt, a German concert manager for the Berlin State Opera, since 2005.
Considers Judy Garland his top gay icon, according to an interview with "The Observer" (21 December 2006).
Wainwright's album "Out of the Game" (2012), produced by Mark Ronson, features Helena Bonham Carter in the title track video.