Loudon Wainwright III may be America's most weirdly humorous Renaissance man - he sings, writes songs, acts and hobnobs with Hollywood's elite, such as director Judd Apatow, who gave him key roles in "Knocked Up," "The 40-Year-Old Virgin" and Fox's "Undeclared." Wainwright, 64, began performing in the '60s, building a body of work hilarious (his only hit was 1972's "Dead Skunk") and poignant ("Hitting You"). He covered '20s country showman Charlie Poole on a superb 2009 album, and he continued with old-timey ballads on last year's "10 Songs for the Great Depression."
Wainwright, who grew up in Westchester, spoke by phone from his Shelter Island home in advance of his Saturday show at Port Washington's Landmark on Main.
In the liner notes to your box set, "40 Odd Years," due in May, Judd Apatow cites your humor as a major influence. When you worked together, did you connect on that level?
There are some similarities, and he's pointed them out. . . . In my show, I'll do funny material, then I'll swerve over into more serious zones. I think Judd liked that about my work, and I certainly like it about his work, too.
When did it occur to you that Great Depression ballads would be so relevant today?
I got a friend out here, Joe Lauro, who lives on the East End. . . . He archives music and films and he sent me an album [of Depression-era songs] called "The Panic Is On," and I thought, "Wow, this would be interesting." It's the same basic problem, but different characters involved, of course. It just seemed like a good idea at the time.
You're the son of a journalist who wrote about his family issues in detail. Your kids have a father who does the same thing. Do you and your kids comment on having that in common?
It seems to be some kind of a family trait, you know, chronicling our lives. My father - I thought his best columns [in Life magazine] were when he got personal, and I've certainly gotten personal, as have Rufus and Martha and Lucy [all singers].
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Any more acting planned in the future?
The trick about acting is to get an acting job. Once you get it, it's pretty easy, but getting it isn't easy. . . . Fortunately, I have folk music to fall back on.
WHEN | WHERE: 8 p.m. Saturday, Landmark on Main Street, 232 Main St., Port Washington
INFO: $40-$45, 516-767-6444, landmarkonmainstreet.org