It’s not often that a Grammy-winning artist who’s played Carnegie Hall comes to play at the Old Whaling Church. But that’ll be the case on Thursday night, July 6, when Loudon Wainwright III takes the stage in Edgartown at 8 pm.
Wainwright is one of the most prolific singer-songwriters in American folk music, or in any genre for that matter. Since releasing his first album in 1970, he’s put out 26 albums, including the Grammy-winning 2010 album “High, Wide, and Handsome.”
His songs can be both sardonic and deeply soulful. He’s made a career out of taking on serious topics, including his own mortality, without taking himself too seriously, with albums like “Attempted Mustache,” “Therapy,” “Recovery,” So Damn Happy, “10 Songs for the New Depression,” “Fame and Wealth,” and “Haven’t Got the Blues (Yet).” He’s captured the spirit of the modern holidays with “Suddenly It’s Christmas”: “Dragging through the falling leaves, /In a one-horse open sleigh. /Suddenly it’s Christmas, /Seven weeks before the day.”
The 70-year-old Wainwright delves into the aging process with songs like “My Meds” and “I Remember Sex.”
He’s also written music for film and theater, and he has a book coming out in the fall, “On Parents & Children, Exes & Excess, Death & Decay, & a Few of My Other Favorite Things.”
He’s the son of the late Loudon Wainwright Jr., whose columns for Life magazine he sometimes recites in concert, verbatim. And he’s a father to some very talented progeny — Rufus, Martha, and Lucy have all established successful music careers.
Wainwright also has an impressive acting résumé, most notably playing a recurring role as Capt. Calvin Spalding, “the Singing Surgeon,” on “M*A*S*H.” Among many other roles, he appeared in “The 40-Year-Old Virgin” and “Knocked Up,” both directed by Judd Apatow. In a Rolling Stone interview, Apatow said, “In my head, Loudon Wainwright is Bono.”
“School Days,” a song you released on your first album, about your high school years at St. Andrew’s School in Delaware, remains a fan favorite. What kind of student were you in high school?
I was pretty average. I was a pretty good football player, high scorer in the conference my senior year. I was good in the school plays, and I had some folk trios. But I was kind of a crappy student. I almost flunked Spanish and didn’t graduate. It was a checkered career. It was the same boarding school that my father want to, so that added a layer of something.
You have hundreds of songs to choose from. How do you decide what you’re going to play. Do you have a set list?
I’ve been known to scribble down some songs. But once the set starts, it can meander and become tangential and go in different directions. People will occasionally yell out requests, which I’ll fulfill or ignore, depending on what they’ve yelled out or how I’m feeling.
What song of yours has been the most successful in terms of publishing royalties?
It has to be “Dead Skunk.” That was a kind of a hit. It got into the Billboard Top 20, and in certain parts of the country, they played the hell out of it.
If the Vineyard had an anthem, that would have to be a front-runner. Have you spent much time here?
No. I’ve only been a few times, and I haven’t been in years. I used to go when the Hot Tin Roof was in operation. I did a show once with Richie Havens there. I think the Roches and I played there once.
You played “Bicentennial” on the first season of “Saturday Night Live,” which was a subtle jab at American politics. Your song and video on Funny or Die, “I Had a Dream,” is anything but subtle in your take on Donald Trump. [“Just like he promised, he built him that wall, /He blew up Cuba and carpet-bombed Montreal.”] How did that come about?
Jill Sobule (“I Kissed a Girl”) and I met at a party in New York, and she started talking about the situation and how we have to write protest songs. I thought it was too obvious, he’s too ridiculous, why even go there? But she encouraged me, so I said, ‘OK, let’s write a protest song.’ As a kid I hitchhiked to the Newport Folk Festival and saw Pete Seeger and Phil Ochs and Dylan sing social-commentary songs. I absorbed that, and I’ve done that throughout my career. So I wrote “I Had a Dream” six months before the election and started playing it, and people thought it was funny. Then he was elected. Now it has a whole other reality.
How did the video with Judd Apatow come about?
Judd and I have a relationship; I did some acting on some of his shows. He was a fan when he was a teenager. So I asked him for some money. He has a bit of that, and he said “OK.” It was a lot of fun.
Is it true you sold your guitar for yoga lessons when you were living in San Francisco in the ’60s?
That is true. I dabbled in it. I probably don’t do as much as I should now. It’s a bit different than it was in 1967. You didn’t see people walking around with yoga mats and bottles of water on their person.
You’re touring the U.K. this summer. You’ve always had a strong following there. Do you think your dark sense of humor resonates more over there?
I don’t know why, but certainly, proportionately speaking, those folks have stuck with it and still show up. I did a tour in the U.K. last fall playing pretty big concert halls. In London I played the Palladium, which is a big venue.
What music are you listening to these days?
Last night we were driving back into New York, I was listening to Lee Wiley, she was a great jazz singer. I don’t listen to a lot of other singer-songwriters. I listen to jazz and classical music mostly.
You acted on one of the most popular TV shows of all time. How did the “M*A*S*H” gig come about?
Larry Gelbart, who created the show, saw me performing at the Troubadour in Los Angeles. He thought, ‘That guy’s kind of interesting, maybe we’ll have a doctor who writes songs.’ It was a lot of fun. I only did three episodes, but I’m sure it’s going to be one of the lead sentences in my obituary.
Since the beginning of your career, you’ve often been mentioned in the same sentence as Bob Dylan. If you win a Nobel Prize, will you go to the ceremony?
You’re damn right. I’ll be there.