Off all the fabled "new Dylans" of the early '70s, none has been as transparent, prolific, and open as Loudon Wainwright III. 40 Odd Years, a box set released this year and produced by Knocked Up and Funny People auteur Judd Apatow, covers 1969 through 2010, from Wainwright's first songs, like "School Days," to "Grey in L.A."
"When we did the box set, I kind of had to go back and listen to everything I'd ever done, which was a harrowing experience, but an interesting one, too." Wainwright explains via cell phone, not sure if he's violating any laws by speaking while driving (a Google search reveals he isn't). "I mean, [there's] a bunch of good songs in there, but it also struck me that despite the fact that more than 40 years have gone by — in terms of my recording career, and my voice certainly has changed a great deal — the things that I write about and the way that I write about them, I don't think has changed that much. So, that surprised me a little bit, although I don't think people change that much. Except, you know, obviously physically. Anyway, that was the kind of observation I came to."
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Over the course of his recording career, Wainwright has balanced personal observations with topical songs, as he does on his latest, Songs for the New Depression. For Wainwright, the occasional shift from intimate to the national is necessary. "It's a good thing," he says. "It's not difficult. It's kind of a release, to get off the topic of me. It was great to, you know, jump into some social commentary, write some topical songs, which I've done from time to time. And, I still bring the same toolkit [to topical songs], to use that horrible expression [laughs]. But the focus is off me for a change. That's kind of a relief, probably for me and the listening public."
Wainwright's work has stretched across disciplines, with the singer/songwriter occasionally popping up in television and movies. He's appeared on shows like M*A*S*H and Parks and Recreation, and in movies like Big Fish, Knocked Up, and For Your Consideration, comedies that share his dark humor. "I thought I was going to be an actor. I went to drama school in the late '60s. When I get an acting job, it's great, and the health insurance is a factor, too. But I'm always waiting for that phone to ring."
Loudon Wainwright III is scheduled to perform Saturday, November 19, at The Orpheum Theatre.
Wainwright earned a Grammy for his 2009 album, High Wide & Handsome: The Charlie Poole Project, which found him appearing alongside his children Rufus and Martha. He's teamed with High Wide producer Dick Connette for his forthcoming record, which finds him once again exploring a persistent topic: himself, and it couldn't boast a more Wainwrightian title.
"I'm pretty sure it's going to be called Older Than My Old Man Now," he says. "That refers to the fact that when I turned 64, I beat my old man. He died at 63." — Jason P. Woodbury