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 One Day I'll Be on Time (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, later divorced, who died in 2010) 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 Take Your Shirt Off (1976) and Final Examiner (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 Real 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 Forever More (Love Songs, Hits & Duets) (1986) were co-produced by British singer/guitarist Richard Thompson. Group 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 Tourist History (1992) and the live Career Moves (1993). A Grown-Ass 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 – Single; the following year, BBC Sessions collected favorites and new compositions. The Last Tour 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. In 2011, Shout! Factory issued a major career retrospective: a five-disc box set entitled "40 Odd Years" that included album tracks, a complete CD of rare and unreleased material, and a 200-plus-minute DVD that included an hourlong 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. Older Than My Old Man Now appeared in 2012, a collection of 15 songs featuring contributions from all four of his children and two of his three wives, and includes a song co-written with late ex-wife, Kate McGarrigle. ~ William Ruhlmann, Rovi