Loudon Wainwright III stands out as a multifaceted creator who sings, composes, writes books, and performs on screen. He first surfaced at the dawn of the 1970s, merging folk, blues, and rock textures while crafting lyrics laced with biting wit, unfiltered self-examination, and pointed social insight. Warm critical responses greeted his opening trio of studio efforts—Album I, Album II, and Album III—while the 1972 novelty single “Dead Skunk” and recurring guest spots on the hit series M*A*S*H expanded his audience and solidified his dedicated following. Over the decades he has issued scores of recordings, among them the Grammy-nominated I’m Alright (1985) and the Grammy-winning High Wide & Handsome: The Charlie Poole Project (2009), and he has taken supporting roles in motion pictures such as Elizabethtown and Knocked Up plus television appearances on Ally McBeal and Parks & Recreation. In 2021 he joined Vince Giordano & the Nighthawks to revisit classic standards on I’d Rather Lead a Band; the following year, at seventy-five, he issued the stylistically diverse Lifetime Achievement, a set of fresh original material. He was once married to the late folk artist Kate McGarrigle and is the father of singers and songwriters Rufus Wainwright, Martha Wainwright, and Lucy Wainwright Roche.
Wainwright spent his childhood in Bedford, located in Westchester County north of New York City, as the son of Life magazine writer and editor Loudon S. Wainwright, Jr., himself a direct descendant of colonial governor Peter Stuyvesant. By the late 1960s he had begun performing autobiographical songs that balanced humor with raw honesty. Atlantic Records signed him, releasing Album I (1970) and Album II (1971), both featuring only his acoustic guitar, before he moved to Columbia for the folk-rock Album III (1972), which contained the Top 40 hit “Dead Skunk.” Follow-up releases Attempted Mustache (1973) and the partly live Unrequited (1975) failed to sustain that commercial momentum, yet his sharp wit and compelling stage presence turned him into a cult favorite and reliable concert draw. Other artists, notably Kate and Anna McGarrigle, began covering his material. He took part in the off-Broadway production Pump Boys and Dinettes and held a recurring role on M*A*S*H. Arista issued T Shirt (1976) and Final Exam (1978), both supported by a full rock band, after which he found a more fitting home on the independent folk label Rounder with A Live One (1980) and Fame and Wealth (1983).
Greater recognition came to him in England than at home, prompting a move to London in 1985. British singer and guitarist Richard Thompson co-produced I’m Alright (1985) and More Love Songs (1986). Therapy (1989) appeared on the major-label-affiliated Silvertone imprint after Wainwright had returned to the United States; he then recorded History (1992) and the live Career Moves (1993) for Virgin’s Charisma subsidiary. His fifteenth album, Grown Man, arrived in 1995, followed three years later by Little Ship. Social Studies, a 1999 collection of topical and humorous songs originally written for National Public Radio since the late 1980s, came next. The BBC Sessions compiled favorites and new pieces in 2000. The Last Man on Earth appeared in 2001, and So Damn Happy marked his Sanctuary debut as a live album in 2003. Here Come the Choppers followed in 2005, then Strange Weirdos: Music from and Inspired by the Film Knocked Up in 2007 and Recovery in 2008.
Shout! Factory marked his fortieth anniversary in 2011 with the five-volume retrospective 40 Odd Years, encompassing studio tracks, unreleased rarities, and a feature-length film containing a documentary plus numerous performances. High Wide & Handsome: The Charlie Poole Project, released in 2009, mixed songs by the folk and country pioneer with new compositions that advanced Wainwright’s singular legacy and earned the Grammy for Best Traditional Folk Album. Older Than My Old Man Now surfaced in 2012, fifteen songs that included contributions from all four of his children and two of his three wives, among them a co-write with the late Kate McGarrigle. Haven’t Got the Blues (Yet), produced by David Mansfield, came out on 429 Records in September 2014.
During Donald Trump’s 2016 presidential campaign, Wainwright penned the satirical “I Had a Dream,” expressing his concerns about a possible Trump victory; he created a Funny or Die video that circulated widely online. Two years afterward he offered the more reflective single “Presidents Day.” Surviving Twin, issued in 2017, captured excerpts from his one-man show exploring his life, music, and bond with his father, incorporating passages from Loudon S. Wainwright, Jr.’s Life columns; the production was filmed for a Netflix special directed by Christopher Guest. That same year he published the candid autobiography Liner Notes: On Parents & Children, Exes & Excess, Death & Decay, and a Few of My Other Favorite Things. Years in the Making, a two-disc compilation of unreleased live and studio recordings spanning his entire career, appeared in 2018. In 2020 he reunited with Vince Giordano & the Nighthawks for I’d Rather Lead a Band, an album of 1920s, ’30s, and ’40s standards rendered in period style. Lifetime Achievement, released in 2022, presented fifteen new original songs supported by settings that ranged from solo guitar to acoustic trios, full-band sessions recorded in Memphis and Nashville, and string ensembles.
