Classic Americana

Classic Americana: Loudon Wainwright III

by Mike Pengra and Luke Taylor

September 05, 2025

Singer Loudon Wainwright III performs during the 32nd Celebrate Brooklyn Summer Season at the Prospect Park Bandshell on July 20, 2010 in New York City.
Singer Loudon Wainwright III performs during the 32nd Celebrate Brooklyn Summer Season at the Prospect Park Bandshell on July 20, 2010 in New York City.Ben Hider/Getty Images

This week’s Classic Americana artist is Loudon Wainwright III, a singer-songwriter, composer and actor who has led a long and varied career. Thursday night, incidentally, Wainwright performed at the Parkway Theater in Minneapolis.

Loudon Wainwright III was born on this day, September 5, in 1946 in Chapel Hill, North Carolina. He studied acting at Carnegie-Mellon University, but like a lot of people in his generation, Wainwright was inspired to become a folk singer after seeing Bob Dylan perform at the Newport Folk Festival. As a result, Wainwright dropped out of college and moved to San Francisco in 1967. The following year, Wainwright wrote his first song and got signed to Atlantic Records, and eventually signed with Columbia Records.

In 1972, Loudon Wainwright III had his first big hit, a novelty song called “Dead Skunk.” Around that same time period, he landed a recurring role on the hit TV series M*A*S*H, one of many acting turns he has enjoyed concurrently with his music career.

But to get to our song selection, we’re taking a track from Loudon Wainwright III’s 1973 album, Attempted Mustache. It’s the opening track on the album, and it’s perfect for this time of year, just past Labor Day, when we’re looking back on the summer that’s recently concluded. It’s called “The Swimming Song,” and it’s a retrospective on the narrator’s summertime swimming adventures. It’s our Classic Americana pick of the week.

“The Swimming Song” got an extra boost after its inclusion in the 2005 film, The Squid and the Whale … and speaking of film, Loudon Wainwright III collaborated with Joe Henry to write music for Judd Apatow’s 2007 film Knocked Up. Wainwright has continued to appear as an actor on the big and small screens, with roles in films including The Aviator and The 40-Year-Old Virgin, and on the TV series Aly McBeal and Parks and Recreation.

But music remains the focus of Wainwright’s career. Since 1970, he’s released 26 studio albums, three of which have been nominated for Grammy Awards — with his 2009 release, High Wide & Handsome: The Charlie Poole Project, winning a Grammy in 2010 for Best Traditional Folk Album. Wainwright’s songs have been recorded by such artists as Bonnie Raitt, Johnny Cash, Mose Allison and Earl Scruggs, and by his son, Rufus Wainwright. In 2023, Loudon Wainwright III was inducted into the North Carolina Music Hall of Fame.

A man smiles with an awards statuette he just won
Musician Loudon Wainwright III poses with Best Traditional Folk Album award for 'High Wide & Handsome: The Charlie Poole Project' in the press room during the 52nd Annual GRAMMY Awards held at Staples Center on January 31, 2010, in Los Angeles.
Kevork Djansezian/Getty Images

Wainwright’s most recent album release is January 2025’s Loudon Live in London, which Folk Alley’s Henry Carrigan describes as capturing Wainwright “at his very best.”

Classic Americana Playlist

Loudon Wainwright III – official site

Classic Americana: Loudon Wainwright III