From a childhood gig as Oliver’s “Artful Dodger,” to a sweep of the 2006 Tony Awards, singer/songwriter Duncan Sheik has left his mark on musical theater – however unintended it was.

Sheik – who struggled to break free of the Top 40 mold after his wildly popular debut album and single, “Barely Breathing” – has crossed over to stage with Spring Awakening, the Broadway smash that’s garnered rave reviews (and all that Tony hardware).

Sheik never set out to write musical theater, but, in the process, discovered a knack for storytelling and narrative music.

Sheik took a break from his current project to chat with us about the trials and tribulations of adolescence, the ups and downs of his recording career, and the eight-year journey that led to the stage phenomenon, Spring Awakening.

Gay & Lesbian Times: As a teenager in the early 1980s, what was adolescence like for you? And what themes did you see from your own adolescence in Spring Awakening?

DS: I grew up in South Carolina and when I was 12, I went to boarding school in New England. Spring Awakening covers a lot of ground in terms of different kids’ experiences in adolescence. Things happen to each of the kids [in Spring Awakening] that touches on something I remember from that time in my life; that enormous rollercoaster of deepest sadness and extreme joy and unrequited desire. It’s a time of real learning and the realization of who you are, and all of those experiences hit you so powerfully at that time. I think that is one reason people respond to the show, because it takes you back to that time in your life.

GLT: Boarding school must be a different dynamic, too. Was it an all-boys boarding school?

DS: In seventh, eighth and ninth grade I was in an all-boys boarding school and then I went to Andover, which was coed. Of course, not being around girls for three years and then having them in the school was … let’s just say it was big. It was a lot to take in. [Laughs.]

GLT: That certainly sounds like a theme we see in Spring Awakening; that sudden realization that there is an opposite sex.

DS: Yes, and you always knew there was an opposite sex, you just didn’t always know what to do with it.

GLT: Some of us still don’t know what to do with it.

DS: [Laughs] Well … [Laughs.] Yeah … that’s [Laughs]. Oh, enough … [Laughs.]

GLT: We’ll move on … You worked on the project with Steven Sater, who wrote the books and lyrics, for more than eight years, correct? During that time, how did the project evolve, and how did your investment in the project evolve?

DS: In 1999, we did our first workshop of the piece with [director] Michael Mayer and Steven and I at the La Jolla Playhouse in October that year; which is why it’s really cool the national tour is kicking off in San Diego, because it feels like it’s really come full circle.

It seemed, initially, during those first few years that within the first few years we’d be putting the show up in New York as early as 2002 or 2003. We work shopped in La Jolla, we did Sundance, we did two workshops at the Roundabout Theatre in New York, so it really seemed that we were set to be on stage five years ago. But, after Sept. 11, the Roundabout started to have budget problems and sort of kicked us to the curb. We had done all this work and at that point it was 2003 when they told us we weren’t going to be doing the show. After four years of work – and things were not going really all that well in my career as a recording artist at the time – it was a really tough pill to swallow. At that moment, it felt like I couldn’t win. Then Tom Hulce came along, and he had been a friend of Michael’s and a fan of Michael’s for years, and he organized a one-night-only concert version of the piece at Lincoln Center in 2005. That kind of resuscitated the piece and that helped us secure production at the Atlantic Theatre, and the rest is history.

GLT: How much time did you actually spend collaborating with Steven on the music?

DS: There would be these bursts of really intense work before and during each of workshops, and by the time the show made it to Broadway we had done seven workshops, so there was a huge amount of development. Every time we did the piece there were several new songs and several cut songs, so it was always evolving, changing, and quite dramatically each time. There were months of intense work before each workshop.

GLT: Working on a project for nearly a decade, when you saw the final staged production, did it have more or less emotional resonance for you?

DS: Much more. I remember very vividly when Steven and I walked into the Atlantic Theatre, and they had just installed all this crazy, intense new lighting in the room. The Atlantic Theatre is like this kind of 19th century church and we had all these neon lights and this really colorful, intense artistry happening. I guess it was during [the song] “The Bitch of Living,” and it was the first time there had been some choreography and they had been in costume and we watched a piece of the real production, and I kind of elbowed Steven and said, “Oh my god, this is really going to work.” It was so exciting to see it fully realized, and just really cool.

GLT: When you work on something for so long, are there points when you say, “I’m done. I’m finished working on this song, on this portion of the production, and I’d like to move forward”?

DS: Yeah, sure. It’s a much more collaborative form than just making records. When I make records, I go into the recording studio and mix an album, I listen to other peoples’ two cents, and I have smart people in the room with me – but at the end of the day, it’s kind of my record and it’s going to sound the way I want it to sound. But that’s not the case in musical theater, because, you know, there are creators, directors, producers and the actors’ interpretations of the material. So, certainly, you know, there were things that I would have done differently, and there was a lot of head butting and very many Waiting for Guffman moments, believe me, throughout the whole development. And there were certainly times I’d be listening to something and thinking “This is the worst thing I’ve ever worked on in my entire life.” But there were also the really amazing, beautiful, kind of profound moments, too, and that’s why we all stuck with it. And, I’m obviously glad I did.

GLT: Tell us a bit about your collaboration with Steven and what the dynamic is like between the two of you. This isn’t the first time you two collaborated. He also worked with you on your album Phantom Moon, correct?

DS: He wrote the lyrics for that record, which is kind of the score of a movie that’s never been filmed. It’s based on a play called Umbridge.

GLT: While you were collaborating on Phantom Moon, you were also working on Spring Awakening. What was that like?

DS: The two things happened simultaneously, and, you know, Steven and I have a very unique collaboration in that we’re almost never in the same room. He just kind of sends me lyrics and I will kind of record a song and I’ll send him back an MP3 and we’ll say, “Hooray, we’re done.” It’s not like we’re sitting around at the piano together and trying this or trying that. He has his process and I have mine and we both really respect that, and that’s what makes it work so well. Once you take the song into the theater and you’ve got the other elements there, then there might be certain changes that happen, but in terms of Steven and I working together, it goes extremely smoothly.

GLT: We’ve heard you tend to work on your own, or shut yourself away while you work on a project. Why is that?

DS: I guess I’m kind of a self-conscious person, for better or worse, and it’s much easier for me to go out on a limb if there is no one else in the room. It’s easier for me to concentrate and not be worried about what other people are thinking. It’s a much more comfortable place for me to be.

GLT: Tell us which song, or songs, in Spring Awakening resonate most with you and why.

DS: One of the most powerful moments in the show for me was always the song “Left Behind,” where Melchior sings about the things that Moritz never got to experience, you know, because he kills himself. And as the song happens, Mortiz’s overly-strict and heartless father stands over Moritz’s grave and realizes what he contributed to his own son’s death, and he’s completely impacted until the very end of the song when he just crumbles. I almost can’t separate the song from the moment in the show. It’s so powerful to me. Other things I’m happy about: “The Mirror – Blue Night” which is a song toward the end of the first act, where Melchior … you really see him transform from a boy to a man in the span of about two minutes, and that’s always felt really successful to me. I think “Touch Me,” too, is like, probably, as a song, my favorite song in the show. Again you see the beginning of awareness of desire – sexual desire – in a young person and there’s this great kind of beauty to that.

GLT: Going back a bit, you mentioned Phantom Moon is the score to a film that’s never been made. Do you like to tell complete stories using an album?

DS: I guess what I realized, almost by accident, is that I really like music to have a narrative aspect to it. I think it enriches what’s going on in the song, to have a really great story underneath it. In my new record that is coming out in the beginning of ’09, it’s called Whisper House, it’s also music for a play, but we’re kind of doing things backward. The music is coming out first and the stage production will happen later. I’ve realized it’s all about telling stories through songs and having this larger narrative and structure to hang the songs on is really appealing to me, and I really enjoy that; that concept of telling story through song.

GLT: Tell us a bit more about Whisper House.

DS: I actually worked on it with a friend of mine, Kyle Jarrow, who is a young writer who graduated from Yale recently, and he’s a really great writer. It’s a ghost story set in World War II. He kind of came up with a story and we went away on a writing retreat to South Carolina last January and wrote the bulk of the songs, and it was a lot of fun. Because it’s a ghost story, I loved being able to write from another persona, of these whimsically malevolent ghosts.

GLT: It seems like you’re really exploring musical theater now, as opposed to focusing only on your recording career and touring. Did you ever expect to fall into musical theater?

DS: Initially, I thought I was going to be somebody who was going to make records and tour and do the normal singer/songwriter thing, and in some ways I was kind of dragged into working in musical theater [laughs]. And, you know, like I said there were things that were very difficult for me to adjust to. Now, after having done it for almost 10 years, I have great respect for the form. My tastes have broadened in terms of things I like by going to the theater all the time and seeing all these classic pieces of theater. Before, it’s not something I would have gravitated towards. When you sit in the audience, you see the incredible richness of it.

GLT: So, before Spring Awakening, were you not a big musical theater fan?

DS: There was a long period of time that I didn’t go to the theater, but as a kid, as a young kid, I did musical theater. I was the “Artful Dodger” in Oliver!. I did a lot of that kind of stuff. But, I guess once you turn 14, 15, playing guitar seems a lot cooler than the musical dance numbers. I think that’s just a natural evolution, but I’ve come back around to it.

GLT: You were working on studio albums while working on Spring Awakening. How did that impact your writing?

DS: I think collaborating with Steven has changed my writing as a lyricist enormously. He’s somebody who has devoted his life to words and he really sees that artistry in his work. He’s made me think much more deeply about how you use words and the sonic beauty that a word can bring to a piece, above and beyond just its meaning. I definitely have a greater appreciation for what it means to write a great lyric.

GLT: Is it fair to say in terms of your recording career you’ve taken risks and chances, that you aren’t predictable and you try new things each time around?

DS: Sure. The problem was in 1996 my first record came out and my first single [“Barely Breathing”] was, you know, a pretty big hit on the radio so all of a sudden … I was, you know, a person who had always listened to import records from England and obscure artsy artists my entire adolescence – and all of a sudden I was put in this top 40 category and it had nothing to do with what I was about, so I spent a long time trying to escape that moniker. With that came a need to make music that wasn’t always commercial. That was very much my intention. I was kind of stiff-arming the whole thing of being a singer on the radio.

GLT: I think that’s evident in the variation among your first three albums. How does a record label respond to that?

DS: Not great [laughs]. There were definitely a lot of strained conversations between myself and the people at Atlantic Records, but I knew I had to follow my path and do work that was meaningful to me, and it was never going to be interesting to me to dumb down my material to be palatable to the late-90s radio listener – that was completely uninteresting to me. It was a tough battle to fight, and certainly, in some ways I lost the battle, and it was working on Spring Awakening that resuscitated my life as an artist, really.

GLT: You seemed to have quite a bit of success, with your fourth album, Daylight, though.

DS: Yeah. Daylight was sort of the last gasp of that kind of normal music business marketing that seemed to infiltrate the culture a little bit. Really, still, I’m really proud of that record. Eighty percent of that record I love and I play it all the time at shows. But I think I hadn’t really hit my stride or found my real thing yet. I think that that came when I started to work with story and with narrative. That’s when I really found the real excitement of writing songs again.