A disciple of Dylan connects with a new generation

Even after 40 years, the name Loudon Wainwright III doesn't exactly roll off the tongue the way Johnny Cash, Joni Mitchell, or Bob Dylan does. But it should.

The singer-songwriter's enduring career proves that sometimes survival alone earns you the right to do whatever you damn well please. Case in point: Wainwright's 2009 album High Wide & Handsome: The Charlie Poole Project. Wearing a sturdy musicologist hat, he channeled his inner T Bone Burnett for a two-disc pet project devoted entirely to the obscure, Depression-era songwriter's life and music.

It scored Wainwright a Grammy for Best Traditional Folk Album earlier this year, paving the way for the recent 10 Songs for the New Depression — a stripped-back read on old songs from the Depression and new originals that summon the spirit of Woody Guthrie.

"It really was an interesting and fun album to do," says Wainwright. "My thought was to track the way things were going for the year and write about it. I like to write topical songs. This time, I thought I would concentrate on very simple songs — stripped back to guitar and ukulele — which was fairly painless and enjoyable, to boot."

Throughout Depression, Wainwright updates songs like W. Lee O'Daniel's 1933 tune "On to Victory, Mr. Roosevelt" and mixes them with originals like "The Krugman Blues," which posits Nobel Prize-winning economist and New York Times columnist Paul Krugman as a source of 21st century blues.

Wainwright says he has no idea if Krugman is even aware of the song. "I hope he heard it," he says. "I've run into him before on a train up to Boston from Washington, D.C. and said something encouraging to him about his work. It must be said that he does have a lovely smile. You don't see it a lot, but he does. I think that's because he believes there's not much to smile [about] in the country right now."

Wainwright somewhat shares that sentiment. He has no clue whether or not there's another Depression in store for this country. "That's not my job, thankfully," he says. "It seems there was a lot of hope in the beginning of the Obama administration that has evaporated.

"But a lot of the guys on the other side don't fill me with anything but anxiety either, which I suppose does a lot to tip my hat about my own political leanings. I'm not a political scientist, but from where I'm sitting, things feel pretty bleak. I'm not feeling pain that others in the country are right now. I have a house that I can't sell, but I still have my job. Hopefully things will improve, but not before I have a chance to cash in on them."

Wainwright could have cashed in on his father's name back in the day. The son of a famous Life magazine writer, the witty and tuneful Wainwright veered off in a different (though equally picturesque) career direction. Inspired after seeing Bob Dylan perform at the 1963 Newport Folk Festival, Wainwright was one of the many folkies who were tagged as New Dylans in the late '60s and early '70s.

It was a label that Wainwright — father of singer-songwriters Rufus and Martha, and ex-husband of late folk icon Kate McGarrigle — never quite lived up to. "Dead Skunk" was his biggest, and only, hit, reaching No. 16 in 1973.

And unlike many of the other New Dylans through the ages, Wainwright's career has also spun off as an actor: He's popped up in several of Judd Apatow's projects, like Knocked Up (Wainwright played a doctor and provided the film's soundtrack) and Undeclared, and he has a recurring role on the TV show Parks and Recreation.

If movie and TV work has changed Wainwright's life or songwriting in any way, it's news to him. "Being an actor is very different from the singer-songwriter world," he says. "I'll sell my CDs after a show and tend to get some younger folks in the lines that are familiar with my acting. [The Apatow connection] has given my career nice little lifts and generational shifts in that regard.

"Working with other actors, writers, and directors ultimately shapes an artistic direction," he says, "whereas my songwriting is much more singular and solitary."

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