Interview: Jack Dolgen on comedy, quitting music and his new album, Wandering Times

Part-time comedian Jack Dolgen goes for the heart on his sophomore album, Wandering Times. © Chanel Raisin

Jack Dolgen is a hard one to figure out. On his new album, Wandering Times, as did on his 2010 debut, Maricopa, he limns the fragilities of the human heart with an exacting detail facilitated by graceful melodies, subtle nuances and engrossing lyrical insights.

At the same time, the singer-songerwriter and guitarist (and onetime bassist for the NYC band, Sam Champion), spends half his time co-writing and producing such gloriously filthy, NSFW Rachel Bloom ditties as Fuck Me, Ray Bradbury and Pictures Of Your Dick.

Clearly, Dolgen is no one-trick pony, which makes it doubly surprising to learn that, after issuing the rapturously received Maricopa, he packed up his instruments and nearly walked away from music entirely. We sat down with Dolgen to talk about why he almost ditched making music and how he balances comedy with poignancy.

Between comedy songs and your straight-ahead singer-songwriter career, do you worry that you're spreading yourself too thin?

"No, I don't, and I feel really lucky about that. I've committed myself to not restricting myself. It's out of necessity, really, so that I don't go nuts. I've been making music for a long time now, in bands and as a solo artist. But I've been able to do a lot of other things in music, too, in terms of producing stuff for TV and films, commercials, and doing the comedy songs. It's cool to stay real busy."

Did you enjoy your experience in the band Sam Champion? Or were you silently cursing having to share the stage with other guys?

"Oh, no, it was great. I loved being in that band. Sam Champion was our thing in college, and we went from playing gigs on the Lower East Side - all these illegal drinker shows and you name it - to kind of falling into a record deal. Things went from there. We did a lot of touring - it was cool.

"Those guys were like brothers to me, and still are. Creatively, there's a lot to be said about working in a group like that, but there's a lot that's great when you can call all the shots on your own. It's been a big change for me to be able to make my own records. It's something I knew I had in me and was a long time coming."

The comedy songs you do with Rachel Bloom are a blast. Did she spark the inner jokester in you, or were you always writing funny songs?

"It started for me a long time ago. The first songs I ever wrote when I was a little kid were parody songs. I remember calling into my local radio station in Tucson, Arizona, on Thanksgiving Day and singing my parody of Michael Jackson's Black Or White, which, in my case, was Dark Or White, referring to the meat of the turkey. Stuff like that.

"I went into doing regular music for a really long time. I had met Rachel, and one day she came to me and said she wanted to do this song and make a video, and she asked me to help her. We sat down and wrote the song, I produced the track, and it just blew up. This was Fuck Me, Ray Bradbury.

"The thing hit, like, a million views on YouTube within five days. It kicked off a new wave in Rachel's career, and we've been adding to it since. Pictures Of Your Dick, You Can Touch My Bobbies - those are some other ones we've done. It's a different side of my music, for sure."

So how does the guy who co-writes Pictures Of Your Dick come up with such a vulnerable song as Baby I'm Afraid Tonight?

"I think, all too often, artists are kind of reduced to a singular identity. The public wants something that's easy to digest, and all too often, artists give them what they want and wind up being one thing: the sad, melancholy, songwriter or the upbeat, party-anthem pop singer. That's an unnatural and false framework that gets applied to artists, and I've tried really hard not to fall into that.

"For me, it's all about honoring the different sides of myself, and to be aware of not ignoring anything and everything that I can do - if at all possible."

You quit the music business for a time after Maricopa came out. What was the story there?

"It was a weird time. I was so thrilled to make the record, and then I hit a kind of postpartum depression. One of the hardest things to do is finish a project, and because that album was such a big part of my life for so long, after I was done I just couldn't handle riding that train anymore. Keep going, promote, all the stuff you have to do with a record - I kind of freaked on the whole thing. I moved to LA, put all my instruments in the garage of my house and said, 'That's it. I'm done.' Making music that I truly cared about... it was too intense."

Meanwhile, songs from Maricopa started popping up in films and TV shows.

"Yeah. A few friends had the record, it got passed around and landed on the desk of a music supervisor at MTV. It went from that person to another music supervisor, who passed it along to a licensing agent, and he came to me and said, 'I'd like to represent your songs for film and TV.' I said, 'Sure, all right.' For me, the album felt like something from the past, so I was like, 'Whatever.' But then things started happening, the songs got placed, and things just escalated."

Did all of the film and TV syncs restore your enthusiasm to give music another try?

"Yeah, it really changed my perspective. I was getting asked to submit original songs for shows, and I figured I'd do that because it was still music, but it wasn't that personal. That worked out pretty decently. After a while, I realized that my desire to ditch music wasn't working - the gods were pulling me back. So I said, 'OK, I'll record a few songs and see how it goes.' Then I kept recording more and more until I found myself totally into it again."

Baby I'm Afraid Tonight - lyrically, where did that come from?

"For me, it was about vulnerability and how important that is in a relationship. But also just in general: So often we represent to each other the best in ourselves or what we want to be... or what we think we should be. We hide the things that we're ashamed of or what we perceive to be our faults. In a relationship, the things that bring people close together are all of it - everything, you know? - especially the more challenging aspects of ourselves. The song is about reaching out. It's a song to a girl, but it's also to myself."

Warning: Above video NSFW!

Why did you decide to release an acoustic version of the song?

"It's fun to strip a song down to the moment where it started. In the studio, I like dealing with production, but it's great to go back home, and you can do that with an acoustic. I'm sort of obsessed with the sound of acoustic guitars."

What are your favorite acoustics to play?

"I have a Gibson J-45. That's the one in the video - it's sort of my main guitar. I have a late '70s Gretsch 12-string that made its way onto some of the songs. I forget what it's called. It doesn't get as much attention as it should; I pretty much use it as a recording tool. Then I have a midrange Martin that I break out from time to time.

"I'm actually better on the bass. I use different basses for different applications, but my mainstay is my '79 Music Man Saber. It's sort of a weird one, but it's cool. It's from before the time that Ernie Ball bought Music Man."

Are you and Rachel working on anything new?

"We're putting the finishing touches on her full-length record. It'll include some of the songs that are out on video already, with new tracks and a few sketches."

You two seem to have a pretty no-holds-barred policy. Has there ever been a subject you thought was just to idiotic to explore?

[laughs] "Yeah, there's always ideas that just won't go. Rachel has a brilliant comedic mind, and she's a great singer, too. Usually, she starts something off, gives me the idea, and we go from there. There's been a few times that we've come up with total duds. We joke about doing parody songs. What's that Gotye song - Somebody I Used To Know? We thought about 'You're just a sweater I used to sew.' That one fell to the floor pretty quickly."