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.