Interview with Loudon Wainwright, smart and clever songwriter who sings about roadkill, reluctant pirates, and his own funeral, in songs both hilarious and poignant.

Loudon Wainwright III, father of Rufus and Martha, brother of Sloan, isn’t your average Wainwright. The folksy Wainwright clan, more and more becoming a dynasty, is by and large associated with pensive melancholy and dramatic gravity. Having heard only Rufus’ and Martha’s precocious, lyrically driven balladry about sexual vulnerability and consumptive desire, you might expect grim tidings from Loudon III, but you’d be mistaken.

Imagine a Wainwright family reunion, the gaggle having just returned from their various global tours, exhausted but ready for a family-wide freeform folk jam. There’s Rufus in the corner moping over his piano, Martha smiling pensively from behind the microphone, and Loudon – well, Loudon would be the life of the party.

Loudon's Prolific Career

Going strong now for 34 years and “twenty-odd” albums, is the mischievous jester of the party, perpetually in a shit-eating grin, entertaining the entire family with his well-timed, clever humor.

He sings about subjects such as roadkill (“Dead Skunk (in the Middle of the Road)”), Tanya Harding (“Tanya’s Twirls”), how bad he’ll look at his funeral (“The Shit Song”), and being a reluctant pirate (“Men”). In “Heaven,” he sings: “There’ll be lots of drinking in Heaven / Smoking and eating and sex / What you didn’t do in this life bad for you / Will be totally cool in the next.”

Humorous Lyrics

Lyrically, his songs are rife with punchlines, but not to the point of gimmick. The wit is kept sharp, not giving way to easy targets or groping one-liners.

"Humor is a way of reacting,” says Loudon. “The world is a terrible, ridiculous place, and I’m perfectly willing to feature all aspects of it. I enjoy making people laugh; it’s a style of writing I’ve developed for over 35 years. [The humor] is designed to amuse, but it’s not a novelty…there’s funny and serious even in the same song. There’re no rules.”

Loudon counts Alan Sherman, Stan Frieburg, and Rogers and Hammerstein among influences, but is reluctant to pin down any specific source of inspiration. “It’s just me. I love being stupid and idiotic; it’s a pleasure for me to be silly,” he says.

He can be serious too. “The Picture” is a sweetly reminiscent song about the sibling politics of childhood, and the distanced adoration of an unwanted father to his child is expressed in “A Year.” His performances feature an unpredictable blend of gently autumnal and goofy, irreverent songs.

Folk Hero Wainwright III

Loudon’s been called anything from a folk hero to a derivative has-been to a cheeky wit. Asked how Loudon would describe Loudon, he laughs and says, “Depends on what day it is. I don’t know, I don’t think of myself in terms of labels. I don’t really care. I just leave descriptions and labels and pigeonholes to the fourth constituency.”

Loudon doesn’t plan on quitting anytime soon; he doesn’t see himself in any other position than making records. “Everything’s relative. Look at Merle Haggard and how prolific he was. I just feel fortunate that songs still emerge. I feel fortunate that people give me money to make albums.”

Loudon is known as well for his frequent bouts of audience inclusion, spontaneously calling out audience members to complete lines or including them in the jokes. In “Between,” he sings, “You’re in between your whole life long, what happens when you die? / …Anybody?”

Loudon is currently on tour. Hear him talk about his songwriting habits in an audio interview here.