Loudon Wainwright III is an economic failure. Over the past 37 years, no less than a dozen record labels (some as large as Atlantic and Columbia, others as small as Hannibal or Red House) have invested in this singer/songwriter, trying to mold his talent into gold records to hang proudly from their walls. They failed. Besides the novelty chuckles of 1972's kiddie sing-along "Dead Skunk (in the Middle of the Road)," which somehow found its way into the Top 40, the man has never produced a hit. He's probably been responsible for more unemployed record label employees than the wrath of downloading. Originally signed as one of the many "new Bob Dylans" (alongside the forgettable Steve Forbert), the career of Wainwright III has been a bottomless financial hole, a walking/talking/singing tax write-off, where record labels dump their cash and never see a return: a complete and total fiscal failure.
But he's our failure. For all the finger waving we do as music fans toward the insatiable greed of record labels, they're hardly in the wrong here. Instead, we are. By last count, Wainwright III has released over 21 records, the heavy majority of which are fantastic, yet still fly under most folks' radar. His finest work in the past few decades has been recent, including Strange Weirdos: Music from and Inspired By the Film Knocked Up, the soundtrack to a surprise hit movie with a staggering box office haul that exceeds $150 million. Yet Wainwright III's songs, for the most part, remain completely unheard, slept on by music fans the world over.
If it wasn't for his champion DNA, which sired two of pop music's most respected singers (Rufus and Martha), or his brief forays in celluloid (As he dryly puts it, "I go on auditions. That's hell."), the man might fall off the earth entirely. Yet the strongest asset of Wainwright III is, and always will be, his bevy of songs, which walk a tightrope between the humorous and the absolutely tragic, and which have a powerful duality to them, featuring both ends of the emotional spectrum.
"When I started, I was almost taking myself too seriously. By my second record I discovered that I could make audiences laugh, and I was delighted by that." He continues, "Since then, I've always succumbed to the temptation to be a clown. But I also discovered that I could do both, and that can be effective."
Wainwright III is the pied piper of lovable losers. He was the original self-deprecating nerd, long before Devo, Elvis Costello, or Weezer polished the bespectacled shine of geek-chic. This is what drew filmmaker Judd Apatow to Wainwright III. He cast the sometime actor in his short-lived, but well-acclaimed, series, Undeclared, in addition to roles in both 40-Year-Old Virgin and Knocked Up. The soundtrack for the latter, Strange Weirdos, finds the eldest Wainwright waxing on the worries, delicacies, and tribulations of parenting, a familiar theme for a man whose personal life, no matter how unflinchingly honest, has always been fair game.
"I've always written about my life and the important people in it, this includes myself, my parents, my siblings, and my kids," he says. "While some people might be uncomfortable with these subjects, I'm not."
It's this openness and fearlessness that softly resonates in his music, as he is a writer unfamiliar with compromise—even if the results are brilliant, but underappreciated. With Wainwright III, failure has never sounded so good.