Loudon Wainwright III grew up in the town of Bedford in wealthy Westchester County north of New York City, the son of Loudon S. Wainwright Jr., a writer and editor at Life magazine and a direct descendant of colonial governor Peter Stuyvesant. Wainwright became a folk singer/songwriter in the late ‘60s, singing humorous and nakedly honest autobiographical songs.
Signed to Atlantic Records, he recorded Album I (1970) and Album II (1971), accompanying himself on acoustic guitar, before switching to Columbia Records, for which he made the folk-rock Album III (1972), which featured the Top 40 novelty hit “Dead Skunk”. Attempted Mustache (1973) and the half-live Unrequited (1975) did not continue that commercial success, though Wainwright’s humor and engaging stage persona made him a cult figure and a concert favorite.
Meanwhile, his songs were recorded by others, notably Kate (his wife, since divorced) and Anna McGarrigle, and Wainwright appeared in the off-Broadway show Pump Boys and Dinettes and played a featured role on the successful M*A*S*H television series. He moved to Arista Records for T Shirt (1976) and Final Exam (1978), on which he was backed by a rock band, but departed the major labels for a more appropriate home on the folk-based indie Rounder for A Live One (1980) and Fame and Wealth (1983).
Wainwright began to gain more notice in England than in the U.S., and he moved to London in 1985. I’m Alright (1985) and More Love Songs (1986) were co-produced by British singer/guitarist Richard Thompson. Therapy (1989) found Wainwright on the major-label-distributed Silvertone imprint and back living in the U.S., and he signed to Virgin Records’ Charisma subsidiary for History (1992) and the live Career Moves (1993). Grown Man, his 15th album, was released in 1995, followed three years later by Little Ship.
In 1999, there appeared a collection of topical, humorous songs Wainwright had been composing since the late ‘80s for National Public Radio, titled Social Studies; the following year, The BBC Sessions collected favorites and new compositions. The Last Man on Earth followed in 2001, and the live album So Damn Happy marked his debut for Sanctuary in 2003. Another studio album, Here Come the Choppers, was released in 2005. It was followed by Strange Weirdos: Music from and Inspired by the Film Knocked Up in 2007 and by Recovery in 2008.
At 65, Loudon Wainwright III is pondering the imponderables with Older Than My Old Man Now (2012). Helping with the heavy lifting are Ramblin’ Jack Elliott, Dame Edna Everage, Chris Smither, Lucy Wainwright Roche, Suzzy Roche, John Scofield, and Martha & Rufus Wainwright. The song treatments range from basic guitar and vocal to sophisticated string settings.