Loudon Wainwright III grew up in the town of Bedford in 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, which released the folk-rock Album III (1972) that 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 and Anna McGarrigle. 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 gained 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, Social Studies appeared, a collection of topical, humorous songs Wainwright had been composing since the late '80s for National Public Radio. 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, followed by Strange Weirdos: Music from and Inspired by the Film Knocked Up in 2007 and by Recovery in 2008.
In 2011, Shout! Factory issued a major career retrospective: a five-volume box set titled 40 Odd Years that included album tracks, a collection of rare and unreleased material, and a 200-plus-minute film with an hour-long documentary as well as dozens of performances. In 2009, Wainwright released High Wide Handsome: The Charlie Poole Project. The set featured songs by the American folk and country icon, as well as new songs that helped move his odd legend forward -- the LP received the Grammy award for Best Traditional Folk Album. Older Than My Old Man Now appeared in 2012, a collection of 15 songs featuring contributions from all four of Wainwright's children and two of his three wives, including a song co-written with the late Kate McGarrigle. In September of 2014, Wainwright released Haven't Got the Blues (Yet), which was produced by David Mansfield and issued on 429 Records.
As Donald Trump was running for president in 2016, Wainwright wrote a satirical number, "I Had a Dream," detailing his anxieties about a possible Trump presidency. He made a video for the song for the humor site Funny or Die, and the tune found a following on social media. (Two years later, Wainwright offered a more serious contemplation of Trump with the single "Presidents Day.") In 2017, he released Surviving Twin, an album that documented Wainwright's one-man-show about his life, music, and relationship with his father, featuring lengthy excerpts from his dad's Life magazine columns; the show was filmed for a Netflix special directed by Christopher Guest. That same year he published his autobiography, Liner Notes: On Parents & Children, Exes & Excess, Death & Decay, and a Few of My Other Favorite Things, a typically candid account of his life and career. In 2018, Wainwright brought out Years in the Making, an ambitious two-disc set that collected unreleased live and studio material from all stages of his career. Wainwright teamed with Vince Giordano the Nighthawks for the 2020 album I'd Rather Lead a Band, a collection of standards from the 1920s, '30s, and '40s performed in authentic style. For 2022's Lifetime Achievement, Wainwright delivered a collection of 15 fresh, original songs with accompaniment ranging from just Wainwright with his guitar to acoustic trios, full-band studio sessions cut in Memphis and Nashville, and string ensembles. ~ James Christopher Monger & Mark Deming, Rovi