Derek Sheen was born a poor, funny child. His mother’s use of comedy as a retreat from the difficult periods in her life rubbed off on the young Sheen, who used jokes to combat school bullies and an abusive stepfather. “Comedy isn’t just a healing mechanism. It’s also a big, fat shield and a weapon when used correctly.” After a brief stint as a child comedian, Sheen shifted to music, only to return to comedy well into his 30’s. Now at 48, the Seattle-based comic has toured with Patton Oswalt, Janeane Garofalo, and Rory Scovel, performed at festivals all over the country, and released three albums, including the recent Disasterbation. I talked to Sheen about his childhood comedy days, his upcoming fourth album, and why he thinks dying in a skydiving accident would give his career a 2Pac-style posthumous boost.
Isaac Kozell: You’ve been on the road a lot recently.
Derek Sheen: Yeah, I’ve been out pretty regularly with Brian (Posehn) the last few weeks. I’m doing a little mini tour here pretty soon and then back with Brian in the middle of November. I’ve been out a lot. It’s been kind of crazy.
IK: You started standup at a really young age. I saw a couple pieces about you, one of which said you started at the age of 13 and another that said you started at 9.
DS: I started really young. We didn’t have music in the house. My mom played comedy albums. That’s what we did for entertainment. I started writing jokes because I liked making my mom laugh. When I was eight or nine she encouraged me to try to get this guy in town who was a musician to manage me. He took me out to a couple of state fairs. That sucked. I hated it. I wasn’t funny. It was a novelty act I did as a kid and kids aren’t fucking funny.
IK: How was it a novelty act?
DS: It was a novelty act in the sense that I did other people’s jokes. I mimicked and did impressions. No one came to see me because I was good. They came to see me because I was a little kid. At that age you just don’t know that there’s nothing you have to contribute to the dialogue. It really burned me out on doing comedy for a long time. I ended up getting into music and dabbled in stand-up here and there. I started going back to open mics when I was 17 or 18. I’d take a bus all the way downtown and go to The Underground. This guy Ron Reed, who was the manager at the time, let me up onstage, but I would have to sit in back because I was too young to be in the bar part of the club. Even then I really wanted to do it, but I didn’t know what the mechanics of it were. I kept dabbling, but ended up playing music for a long time because I had crippling stage fright. It was so bad at one point that I couldn’t even speak publicly, so I pushed myself into things like dramatic arts. I started drama class and playing music in the jazz band, anything where I could get onstage and make myself be out there and try to… what do they call it, aversion therapy? That helped me get back onstage. I played music professionally for about 15 years. At the point where I quit playing music I was literally onstage every night just talking to the audience. The band, we barely played. I would just tell jokes and talk to the audience. We decided one night, “Let’s just not do this anymore. Clearly your heart’s not in it.” I started going back to open mics and I felt really confident. I really didn’t start comedy again until I was 35.
IK: How old are you now?
IK: I started late too. I was raised in the church and was onstage from the time I was young, doing Bible readings and stuff. I eventually did the band thing too. I was comfortable being onstage, but I didn’t start standup until I was 31. Comedy came pretty late for me.
DS: Me too. I think I needed to go through all that stuff. I needed to have all the life experience and be in music. All of that really informed my personality. I wish I would have started stand-up seriously when I was young, but I think I would still be at the same place I am now. I don’t think I would have progressed any faster because I would have had the exact same circumstances. I just would have been doing stand-up. I had that period where I was motivated, hungry, and making art, but at the same time you’re damn near homeless, your relationships are falling apart. You have to go through all that stuff before you become a full person. I’m kind of glad I started when I did because all of that shit was out of the way. I could really just focus on the craft and not have to worry about, “Where am I going to live next month,” “I have eight roommates,” “Why do we have cockroaches,” “Should I date this girl,” “What are my feelings?” I was past that. At 35 I was smooth granite at that point. The whetstone had paired me down.
IK: And now your third album just came out.
DS: Yeah, and the fourth one…I’m going to try to pull off a trick this year where I actually release two albums. The third one took a year-and-a-half to get it out, so I’m already at a place where I’m going to record the new stuff. I’m going to try to get it out by September. But the third one I’m really happy with. It was all b-sides of stuff from when I did Tiny Idiot, my second album. I still had material that I wanted to use, but it wasn’t ready. I went out and worked that material for six months and then we recorded it.
IK: You recently posted on Facebook a list of goals you want to achieve in the next year. One of them was that you want to learn to play saxophone.
DS: I played guitar for a long time, bass and drums, a little bit of piano, woodwind, but it was bagpipes. I’ve always wanted to play saxophone. I just really love it, especially tenor sax. I bought some finger charts and a couple of lesson books. I already read music and played music for so long, so I feel like it’s just about learning how to use my armature, my lips, and learning how to breathe. Plus, you can take a saxophone anywhere. You don’t need an amp. You don’t need to plug it in. You just play saxophone. I feel like it will be another way to express myself musically because I still love to woodshed and doodle when no one else is around. I also want to learn how to speak Chinese because I think it’s going to be really important. And then what was the fourth one? Was it skydiving?
IK: Yeah, you said you wanted to confront your fear of heights.
DS: That shit is happening in December on my birthday. I bought the $250 first timer training thing where you take an hour lesson, pack your parachute, and do a tandem jump where you go with the trainer and they’re attached to you. I’m terrified. It’s so helpful when people say, “I lost a friend skydiving,” or, “I had a friend of mine who was a trainer and his parachute didn’t open.” It’s like, “Thanks for letting me know that.” But I’m going to do it anyway. Fuck it. If I die skydiving, how cool is that? “Oh my God, he wanted to skydive to conquer his fear of heights and died on the first jump.” That’s the most awesome ironic death and if it doesn’t help sell my back catalogue I’d be surprised.