15 Minutes With Loudon Wainwright III

He’s 65 years old now, but when he first started making albums he was called a “new Bob Dylan.” Loudon Wainwright III returns to the Cactus Cafe this weekend for shows on Saturday and Sunday nights.

Still one of the best singer-songwriters of his generation, he’s been very active of late. Last May saw the release of the 4-CD/1-DVD box set 40 Odd Years, a fab overview of his career chronicling his life – our lives – in song.

Wainwright also has a new album, Older Than My Old Man Now, a reflection on mortality with contributions from his entire family, including his father who wrote and later edited LIFE magazine as well as his children Rufus, Martha, and Lucy.

Geezerville: Tell me about the making of the box set. You made all the choices in what songs were included.

Loudon Wainwright: Yes, I termed myself “The Decider.”

G: Was it a long process?

LW: A couple of months. But I hadn’t listened to a lot of the stuff for years and years. That was the albums themselves and then I tried to root around and find some bonus tracks. There were lists made and then the painful decision of what went and what stayed.

G: There are things on the DVD that are amazing. I mean that they even exist.

LW: The DVD I worked less on. I saw everything, but [film director] Judd Apatow became very involved in working on the DVD. You can’t really underestimate his effect on the overall box set and in particular the DVD.

G: Was putting together the bonus disc of rare material a chore?

LW: I had old tapes, reel to reel, cassettes. Like any musician that’s been doing stuff for 40 years [he pauses to chuckle], you’re basement might be filled with stuff.

G: I'm curious whether you took care of that kind of stuff. I think a lot of older artists are wary of putting out a box. They view it as the last nail in the coffin. With the new album you talk about not having to write an autobiography, that you do it in song. I think the box set serves that purpose very well.

LW: That’s good to hear. Originally I was going to group songs together in some kind of category. You know, family songs, or novelty songs, but it became obvious that chronological was the way to go. So it does tell the story of what’s been going on in my life.

G: To me you talk for a generation. You write about things that are personal, but they're universal in ways that are funny and tragic. Things that we can all identify with as we grow older.

LW: The identification factor is why, to use a highfalutin word, art works. An audience, no matter where they are, they get pulled into what’s being presented to them. It affects their personal lives. So I’ve been writing about me, but the same things have been happening to everybody else and if it hasn’t it will.

G: Has there ever been a period when you weren’t writing songs or maybe a time that wasn’t as prolific as others?

LW: I’ve gone through dry spells. Months where I haven’t written songs. But I’m fortunate I haven’t gone through any major writer’s block. I’m not as prolific as I was, but there’s a lot of things that I don’t do as much as I used to.

G: In the past few years you’ve written songs for film and a play. Is that a different writing process?

LW: It is and it isn’t. If you get an assignment, once you starting writing the same muscles are working. In the Seventies when I was in the TV show M*A*S*H, I had to write very specific stuff about Douglas MacArthur and going to Tokyo. Stuff that I had no real experience with, but I found then that I could write to order and to deadline.

G: Your entire family is represented in one way or another on the new album.

LW: I obviously have a very musical family. I knew going in that this record was going to be about mortality, but it’s also about family. My father’s even in it. Besides the family guests, I have Ramblin’ Jack Elliot, Dame Edna Everage, and Chris Smither.

G: People always come away from your shows thinking about the moments of terrible sadness that were balanced by moments of straight up hilarity. Was that something that developed over time? I seem to remember you being very straight laced when you started.

LW: There was a song on my first record in 1969, “I Don’t Care,” that has a hint of comedy in it. I mean I took myself seriously as a young man, but very soon.... On my second record there was a song called “Nice Jewish Girls,” which was a novelty song. I’ve always liked writing novelty songs. In my shows I enjoy making people laugh when I can get away with it. It gives it some variety. I don’t want to be bumming people out for 75 minutes. I suppose there are people that like that, but I don’t. I have to be entertained too.