Catching Up With Loudon Wainwright III

Loudon Wainwright III released his first album in 1970—and despite the fact that his lone brush with the Top 40 occurred two years later, with the borderline novelty track “Dead Skunk,” he’s kept right on making records ever since. And at a pretty good clip, too: at last count, he’d amassed 21 studio sets and three live albums, all full of pointed observations on the human condition that blend laughter and sorrow with a kind of delirious, imperfect grace. Kind of like real life, you might say.

Wait—make that 21 studio sets, three live albums, and one box set. Today, Shout! Factory releases the aptly named 40 Odd Years, which distills Wainwright’s oeuvre into three chronologically sorted CDs of “hits,” a disc of demos and assorted rarities, and a bonus DVD packed with documentaries and live performances.

It’s the kind of treatment usually reserved for artists with household names—or, as Wainwright would be quick to joke, those who are already dead—but even if superstardom has eluded him, Loudon Wainwright III has amassed plenty of accolades (and classic songs) along the way, and 40 Odd Years serves as both a persuasive argument and a compelling introduction.

Wainwright is on the road, heading for a medium-sized venue near you, but he took a few minutes to check in with Paste and discuss the box, his career, and what comes next.

Paste: We see a lot of artists feigning indifference when this type of collection is released, so it was refreshing to read in the 40 Odd Years liner notes that having your work compiled this way was meaningful to you—and to see you take the opportunity to thank Judd Apatow for helping make it happen. It’s a nice contrast to the “don’t blame me, blame the label” approach.
Loudon Wainwright III: Well, I was on so many labels, I wouldn’t know where to begin. [Laughs] I had 15 different labels or something, which was difficult when it came time to license the songs. But no, I’m very happy to have a box set, particularly before I’m in a box myself.

I’m very appreciative of Judd’s efforts to make the box set happen. And it’s about damn time, I’d say. [Laughs] But I got very involved. I spent a lot of time listening to everything, trying to decide what went on and what didn’t. That was kind of painful, but I’m a masochist. I even got involved with the artwork, along with my designer, a guy named Adam Tuck.

So I was very involved, but I certainly needed Judd’s help. This wouldn’t have happened without his good graces.

Paste: With this arriving just a few years after the Recovery album, which found you re-recording songs from your earlier catalog, it’s hard not to conclude you’re in a somewhat reflective state of mind.
Wainwright: A looking-back state, as it were. Well, I’m 64 now, so there’s certainly less time left than has been spent. I don’t know if that’s grammatically correct, but I think we have a tendency to look back as we get into our ‘60s—not just in our own lives, but in the lives of our ancestors. We develop interests in family trees, the Civil War—I don’t know what it is. Well, I do know, actually: You’re getting ready to be an ancestor yourself.

Paste: Obviously, you had more room to fill with this project, but were there any other ways that the song selection process differed between Recovery and 40 Odd Years?
Wainwright: Well, in the case of Recovery, I worked with the fabulous Joe Henry, and Joe is very familiar with my material. He got into my music as a teenager, and he knows the songs, so we just spent time talking about what would work. And we had in mind this great band that Joe works with, so we matched them up that way—and we limited ourselves to my first four albums, too. We just talked about what would be fun with those guys. It was a fun record to make.

The process for the box set was agonizing. As I say in the liner notes, it was akin to drowning kittens. Some songs got left off for the simple reason that there are only 80 minutes on a CD and I had to cover 24 albums. I can’t do the math in my head, but if I’ve got 12 songs on an album, and 24 albums, well…that’s a lot of songs. We had to whittle it down to 62 songs or whatever it is. But there is a bonus CD, and then a two-hour DVD, so I think people will probably be sick of me by the time they’re done with it all.

Paste: Taken together, it all tells a pretty fascinating tale. I wondered if any of these songs still surprised you—for better or for worse. Did anything make you wince?
Wainwright: Yeah, I even forget about certain songs. There are a lot of them. It’s a lot of work I’ve done. Maybe it’s my tendency to loathe myself, but I tend to think of myself as sort of a lazy bum—but in fact, I’ve written a lot of music, and some of it is pretty good. So maybe I’m not so bad after all. [Laughs] Maybe I’ll tell that to my therapist.

And you know, a song can make you wince and still be a good song. For instance, there’s a track on the bonus CD called “Laid,” which I never had enough guts to put on a record. It’s a live track, and you can hear the audience cringing. I winced again, but I thought, “Yeah, I can put this out now.” Wincing is good.

Paste: You’re an artist who’s really helped develop the art of leading the audience into some dark places while delivering some unexpected laughs along the way—sometimes in the space of a single song.
Wainwright: I’m a traditional enough guy to believe that my first job during a 90-minute show, or an 80-minute album, is to deliver a satisfying experience. And one of the things I’ve done for years is try to leaven things with humor, because things are ridiculous anyway. Even if you’re writing about a divorce or a death or the end of the world, a joke can help. It makes the whole thing more enjoyable—not only for the audience, but for me.

I think what happens with any kind of writing—or painting, or architecture, or acting, for that matter—is that you develop a style. You don’t think about it too much. I don’t decide “I’m going to put a joke in here,” the songs just evolve naturally because I write them the way I write them.

Paste: Did assembling this reveal anything to you about your songwriting process? Did you notice a change?
Wainwright: I’m not really aware that it’s changed. I mean, sometimes I’m surprised when I look at myself in the mirror—I don’t feel any different, but then I see what I see and I think, “Holy shit.”

Maybe it’s changed, but I’m not really thinking about it. I’m too focused on trying to get the next one. I don’t understand how it works—it’s mysterious. I don’t want to fuck with it. When a good song comes to the surface, it’s a small miracle to me. I still feel that way.

Paste: You’ve released some of your best work in the last 10-15 years. Do you feel like you’re developing a firmer grasp on that mystery? Getting more confident in the process?
Wainwright: I’m not more confident, but I am more grateful when something happens, because I know there’s a time limit on anything. It’s a bit like sex, you know. It starts out happening all the time, and then it slows to a trickle, or a drip, or something—I don’t want to get too disgusting. But it’s a miracle no matter what.

Paste: What’s next for you? Have you started thinking about your next project?
Wainwright: I have—I’ve got a batch that I think are good songs and that are of a piece, in a sense. I just have to figure out how I want to produce it, who I want to work with, and who’s going to pay for it. [Laughs] I have to trick someone into giving me money again. That’s hopefully the next step.

Watch a video of “Dead Man,” the new song Wainwright recorded for 40 Odd Years.