Wainwright was born in Chapel Hill, North Carolina, the son of Martha T., a yoga teacher, and Loudon Wainwright, Jr., a columnist and editor for Life magazine. Wainwright grew up in Bedford, New York, a town in Westchester County. Among his sisters is Sloan Wainwright, also a singer. He graduated from St. Andrew's School.
Wainwright's career began in the late 1960s. He had played the guitar while in school, but would later sell it for yoga lessons while living in San Francisco. Later, in Rhode Island, Wainwright's grandmother got him a job working in a boatyard. He was inspired by an old lobster fisherman named Edgar to borrow a friend's guitar and write his first song (entitled "Edgar"). Soon after, Wainwright bought a guitar and in about a year, he had written close to twenty songs. He decided to go to Boston and New York and began playing live shows in folk clubs. He was eventually "discovered" by Milton Kramer who became his manager. He acquired a record deal with Atlantic Records who released his first album in 1970.
Wainwright is known for the 1972 novelty song hit "Dead Skunk (in the Middle of the Road)" and for playing Captain Spalding (the "singing surgeon") on three episodes of the American television show M*A*S*H in its third season (1974-1975 including episode Rainbow Bridge), but his musical reputation is much deeper. Using a witty, self-mocking style, Wainwright has recorded over twenty albums on eleven different labels. Two of his albums have been nominated for Grammy awards.
Wainwright has also appeared in a number of films, including small parts in The Aviator, Big Fish, The 40 Year Old Virgin, Knocked Up and the television series Undeclared. Wainwright came to the attention of many people in Britain for the first time when he appeared as the resident singer with comedian Jasper Carrott in his UK show, Carrott Confidential, in the late 1980s, and he has remained popular in the UK ever since.
Wainwright has claimed that, like many of his contemporaries, he was inspired musically by seeing Bob Dylan at the Newport Folk Festival in 1962. He was one of many young folksingers tagged as the "new Dylan" in the early 1970s, a fact that he later ruefully satirized in his song "Talking New Bob Dylan" from 1992's History album.
In September of 2006, Wainwright and musician Joe Henry began composing the music to the Judd Apatow film, Knocked Up, which was released on June 1, 2007. In addition to composing the soundtrack, Wainwright appeared in the film in a supporting role as the protagonists' obstetrician.
Wainwright's son Rufus Wainwright and daughter Martha Wainwright by his onetime marriage to Canadian singer/songwriter Kate McGarrigle are both singer/songwriters as well. Rufus was the subject of two of Loudon's more famous songs, the breastfeeding ode "Rufus Is a Tit Man" and the retrospective "A Father and a Son", while Martha entered the world to "Pretty Little Martha", turned five to the post-divorce child-rearing anthem "Five Years Old" and entered her teenage years with the brutally clinical "Hitting You". Rufus, in turn, has covered his father's "One Man Guy" and wrote "Dinner at Eight" about a family dispute, while Martha has covered her father's "Pretty Good Day" and wryly states that her song "Bloody Mother Fucking Asshole" is about her father. On the other hand, Martha and Loudon collaborated on the song "You Never Phone" on his album 2003 So Damn Happy.
Loudon also has a daughter, Lucy Roche by the singer Suzzy Roche, and a third daughter, Lexie Kelly. Loudon remarried in 2005.
He is one of the inspirations for Doonesbury minor character Jimmy Thudpucker.
Attempted Mustache (1973)
1. The Swimming Song
2. A.M. World
3. Bell Bottom Pants
5. I Am The Way (New York Town)
6. Clockwork Chartreuse
7. Down Drinking At The Bar
8. The Man Who Couldn't Cry
9. Come A Long Way
10. Nocturnal Stumblebutt
11. Dilated To Meet You
T Shirt (1976)
2. Summer's Almost Over
3. Hollywood Hopeful
5. At Both Ends
6. Wine with Dinner
7. Hey Packy (George Gerdes)
8. California Prison Blues
9. Talking Big Apple '75
10. Prince Hal's Dirge
11. Just Like President Thieu
12. Wine with Dinner (Night Cap)
* Kenneth Buttrey - drums
* Johnny Christopher - acoustic guitaar, electric guitar
* Tommy Cogbill - bass
* Ron Cornelius - acoustic guitar, electric guitar
* Mac Gayden - acoustic guitar, electric guitar, slide guitar
* Reggie Young - acoustic guitar, electric guitar
* Pig Robbins - piano, organ
* Doug Kershaw - fiddle and cajun exclamation
* Loudon Wainwright III - acoustic guitar, banjo, vocal
* Kate McGarrigle - banjo, vocal