Almost 40 years into his career, Grammy Award–winning folk singer, humorist, and actor Loudon Wainwright III makes his headlining debut at Carnegie Hall with a concert in Zankel Hall on January 26. Jay Ruttenberg recalls "an incredibly uncomfortable" moment he shared with the artist he describes as "a Judd Apatow character marooned in 1970s folk."
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. Overtime, 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).
Loudon Wainwright III performs "The Swimming Song."
Related: January 26, Loudon Wainwright III