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).