Loudon Wainwright has written biting songs about love ("It's Love and I Hate It"), the end of love ("Your Mother and I," "Whatever Happened to Us?"), family ("Your Father's Car," "White Winos") and kids ("Be Careful There's a Baby in the House," "Father/Daughter Dialogue"). His biggest hit was a 1972 novelty about road kill ("Dead Skunk").
In recent years, though, Wainwright, 64, has begun considering mortality -- and looking back. He offered up a renewed greatest-hits set in 2008's "Recovery," re-recordings of some of his favorite old songs. The following year, Wainwright resuscitated the catalog of a lost Carolina country legend in "High, Wide & Handsome: The Charlie Poole Project." Now he's back with his own legendary-status project, "40 Odd Years," a box set of Wainwright's 40-year career featuring four discs of his bittersweet, intensely personal folk songs (three from the albums, one of outtakes and rarities), plus a DVD of filmed performances. It's out May 3 from Shout! Factory.
"Well, you want to get the box out before you're in the box yourself," Wainwright said during a recent chat. "I've had interest in a box set on a couple of occasions, but my friend and patron Judd Apatow" -- Wainwright has worked on several of Apatow's projects, including scoring the film "Knocked Up" and acting in the TV series "Undeclared" -- "he's got a good relationship with the guys at Shout! Factory, and he kept nudging them, 'C'mon, guys, Loudon needs a box.' Without his help, it might not have happened.
His 40 years of making music has worked in conjunction with nearly 20 different record labels, so assembling a Wainwright box took some doing. He chatted with me from his Long Island home about boiling down his life's work, dredging up some rare tracks and looking ahead.
with Kim Richey
• 7 and 10 p.m. April 15
• Old Town School of Folk Music, 4544 N. Lincoln
• Tickets: $24-$28, (773) 728-6000, oldtownschool.org
Q. Did the process of evaluating your catalog for this box set begin when you reconsidered old songs for the "Recovery" album?
A. If you've been doing this and as you get older, you look back. Can't help it. In my songwriting, I seem to be doing a lot of that lately. It has to do with coming to the end of something, I guess. "Recovery" was a way of revisiting songs, some 40 years later, in the context of the band I work with out in L.A. This box set starts all the way back to the first track of the first record.
Q. Did you select the tracks?
A. Yes, I had to pick the tracks, which was very painful. A lot of things didn't make it. You only have 80 minutes on a CD. Hopefully it has some sweep for the listener, some interest for old fans and new fans alike.
Q. How did you make your choices?
A. Some people let others decide for them. I could have gone that route. I have friends who are familiar with my canon and whose judgment I trust. I checked in with those people and asked their opinion on what was essential. I requested the same of some fans that I've met at gigs over the years -- they always seem to be guys. At the end fo the day, it was difficult. In the liner notes I say it was like drowning kittens. I left off some of my favorites.
Q. Like what?
A. Two songs: "Missing You" and "Man's World." Those are favorites of mine, but there was just no room for them.
Q. Yet you included a lot of extras on the bonus disc. Tell me what transpired to make you feel that "Laid," a song you say you always felt was too mean to put on a record, is OK to lay out there now?
A. It's a little rough, but I like it. The idea of bonus tracks is to put out stuff people wouldn't normally have heard, and "Laid" fit right into that pocket. "Laid" is a pretty bleak look at getting laid. It's not something I do anymore. It's just an interesting snapshot of where I was at the time.
Q. Were there discoveries for yourself when digging up some of the rarities?
A. Well, in terms of the bonus tracks, yeah. There's a song on the box called "McSorley's," which is a song I only performed about three times, in 1970. The oldest saloon in New York's East Village was this Irish bar called McSorley's, and until 1970 only men were allowed. Coinciding with the rise of the women's movement, there was a lot of pressure put on the place and that tradition was broken. They forced it to go co-ed. At the time, I was a twentysomething sexist pig and wrote this song as a kind of protest. This was a great tradition, women are turning into men, that sort of thing. It was very sarcastic. I think politically I've moved away from that stance [laughs], but I put it on the box as an interesting look at where I was in 1970 -- wistful about the idea that there are bars where only men can go.
Q. You talk about these songs as if they're photos in an album.
A. That word "snapshot" is very good here. These songs are three-minute pictures of something. There's a lot of stuff behind them -- the good songs, anyway.
Q. Do you enjoy going back and listening to the old stuff?
A. [A pause] I'm not a guy who sits around and listens to his own records. That's not my idea of a good time. When you make a record, you listen to it hundreds of times; you kind of wallow in it. Once it's out and you can't change anything, I don't want to hear it again. I'm not going to be listening to this box set.
Q. The Irish version of "The Hardy Boys at the Y" on the box was nice to hear. It makes much more sense in that arrangement. I never understood why the ends of the verses repeat until now.
A. I love that kind of music. The Boys of the Lough, the Bothy Band, Christy Moore -- we knew each other playing folk festivals. I can't recall why we didn't put that song out this way instead of the live version [on 1975's "Unrequited"].
Q. Tell me about writing "No Sure Way."
A. I once lived in Brooklyn Heights, a beautiful part of New York, and there's this thing called the Promenade Walk out there where you can see all of lower Manhattan. When 9/11 happened, I was out here in this Long Island house, and I went back a day or two later to the Promenade and looked at that ... smoking mound, I guess is what it was, of rubble and humanity. When you face something that huge, you think, "I'm not even going to think of writing a song about this. It's too ridiculous and too maudlin." I'm sure there are hundreds of songs written about 9/11 now. But later that week I found myself taking a subway ride that went directly underneath the mound, and I wrote and recorded this song three days later. Like the words I used in the song, it felt "obscene."
Q. In the liner notes, David Wild describes you as "fearless." Do you feel fearless?
A. In my part of the liner notes, I address that point that David and others have made. Take the song "Hitting You." It's about hauling off and hitting [daughter] Martha. That's an example, I suppose, of a fearless song. If you're at a performance in a dark room with lights on you and a microphone and people are sitting there listening, it sounds and looks fearless -- but it's a natural habitat for me. I feel pretty safe. I'm aware of the fact that I'm getting into areas that maybe people have strong feelings about, but for me it feels quite natural, not any act of courage. It's what I do. It's my shtick. I write about my personal life and the people in it. I haven't masked it too much. It's just what I do.
Q. That's what folk music is supposed to be all about.
A. It's about what's happening to you, and what's happened to me is in manyways what's happened to everybody. My life is not particularly unusual. There's identification. That's what art is about. People say, "I know what he's talking about."
Q. I read that [Wainwright's son] Rufus is assembling his own box set, true?
A. Yes, Rufus and I are recording a song next week to be on his bonus disc.
Q. What song?
A. "Down Where the Drunkards Roll" by Richard Thompson.
Q. And congratulations on becoming a granddad again. [Rufus Wainwright announced earlier this year he and his partner became parents to a child, Viva Katherine Wainwright Cohen, via Lorca Cohen, daughter of Canadian singer Leonard Cohen.]
A. Thanks. I was in L.A. when Viva arrived. I love being a grandparent. It's so much easier.
Q. What's next?
A. Writing new songs, and I suspect I'll think about making another record.
Q. Any acting gigs?
A. I have an audition tomorrow! Thank heaven I have folk music to fall back on.