Loudon Wainwright III is the son of a journalist: the late
Loudon Wainwright Jr., whose columns for
LIFE magazine were potent enough so that, to this
day, elderly strangers still approach the musician with inquiries
about his namesake's work. And from the beginning of his career, a
strong journalistic streak has run through Wainwright's songs. He
sings with wit and easy mordancy, his work covering similar turf to
that of an old-fashioned newspaper columnist: family, politics,
golf, McSorley's Old Ale House.
Yet in the grand scheme, Loudon Wainwright III is not a son, but a
father. In decades past, many of his best songs were written about
his young children. Over time, various Wainwright progeny—Rufus,
Martha, Lucy—have grown into their own music careers, where many of
their best songs involve Loudon. Still other artists have
adopted the singer as a kind of surrogate dad. Most prominent is
Judd Apatow, who habitually turns to Wainwright's work for its
paternal air; he even cast the musician as his protagonist's nudnik
father in the sitcom Undeclared.
In 2011, the filmmaker co-produced 40 Odd
Years, Wainwright's career-spanning box set. To listen to
the collection is to witness an artist ahead of his time—not in
terms of musical style, but rather in disposition. Wainwright, it
turns out, was never a fabled New Dylan or novelty songsmith, but a
Judd Apatow character marooned in 1970s folk. His four-decade
repertoire reveals a mildly neurotic figure who is quick with a
joke, baldly sensitive, and in possession of a mean streak.
Frequently, he is involved with women who appear to be out of his
league and, thus, he seems to be forever stuck in some sort of
romantic muddle. And in classic Apatow form, the singer falls into
a chasm between social casts: preppy and hippie, nerdy and cool,
privileged WASP and perennial outsider.
Wainwright is one of those singer-songwriters whose work is said to
crawl under listeners' skin at odd junctures of their own lives.
Personally, I had never found this to be the case. But then, not
two years ago, it ensnared me at just such a time and in no
uncertain terms. As it happened, I was scheduled to interview
Wainwright at his home out on Shelter Island, an unusually charmed
sliver of Long Island reachable exclusively by boat. The day before
the interview, I came to the office toting my overnight bag. (In
order to catch the ferry, I would have to set out from Penn Station
that afternoon.) Arriving at work, the elevator doors opened onto
an ominous meeting. The magazine's entire staff was present,
alongside representatives of the kindly private equity group that
had just acquired it. A corporate bloodbath! After our decade
together, the magazine had decided to make its way in the world
without me.
All rules of logic dictated that I scratch the interview and slink
home, but fleeing Manhattan seemed like a smart idea. After all,
nobody wants to be around the recently laid-off. The city should
quarantine us like lepers, clutching our boxes of sad memories and
stolen staplers while mumbling to anyone within earshot how our
erstwhile offices will never function without us. And so, mere
hours after receiving my walking papers, with nary a single
farewell e-mail sent or weepy phone call placed, I found myself
drifting away from the mainland aboard the Shelter Island ferry. It
was the last day of May, and the world smelled like summer
camp.
The next morning, Wainwright pulled up to my hotel in a Volvo,
wearing glasses and a dad-hat. At his house, the singer spoke of
his life on Shelter Island, his early efforts to separate himself
from his peers (no bellbottoms!), his forays into acting, and his
habit of writing songs that glorify the mundane. "The big things in
the average person's life are the romances that they have, and then
the destruction and loss of them," he told me. "Parents, siblings,
children, the death of parents, family tension ... these are
monumental things. They struck me as being interesting to write
about. I didn't have a very exotic life, but all this stuff
happened to me."
There was a lull in the conversation. "I got laid off yesterday!" I
blurted out. I regretted my lapse of professionalism almost
immediately, but a dam had burst. Therapeutic clichés began to
spill from my mouth. It dawned on me that Wainwright was the first
person outside of my family to hear this news. I was turning to the
singer, a virtual stranger, in search of some sort of paternal
consolation that was not his to provide. We both seemed incredibly
uncomfortable.
Come evening, I returned to the city and my apartment. A disc from
the musician's box set had been left in the stereo. "This summer I
went swimming, this summer I might have drowned," Wainwright sang.
"But I held my breath and I kicked my feet and I moved my arms
around." And there—in these funny, lonely, angry songs—was all the
solace I had been seeking.
Jay Ruttenberg is editor of the comedy journal The Lowbrow
Reader and of the book The Lowbrow Reader
Reader (Drag City, 2012).