Singer-Songwriter. Über Geek. Work Horse. Funny Man. Loving Father… all phrases that describe web phenom Jonathan Coulton. Don’t take our word for it, though, listen to any one of his eight full length albums, and you’ll agree: DUDE. IS. AWESOME.

Jonathan took a moment away from his grueling performance schedule to speak to us about his comedic and musical influences,  what it was like to ditch his Yale degree to pursue a musical comedy career, and what  it’s like to be best friends with a fellow nerdcore celebrity.

ROOFTOP:  Music is awesome. Comedy is awesome…but not always at the same time. Either the quality of the joke doesn’t always match up to the quality of the song, or it’s funny, but the song sucks. What’s special about your body of work is that the songs are actually good AND incredibly funny. The “Flickr” song is an perfect example of this. It’s so catchy, technically sound, heartfelt, AND hilarious. What’s your secret, hotshot?

JONATHAN COULTON: Comedy always works better when you take it seriously. And for me that means giving every song the best musical setting I can, whether it’s funny or sad or in between. I’m a sucker for songs that tell a story and make you want to sing them, so that’s what I’m always trying to write.

ROOFTOP: We heard you’re old college buddies with John Hodgman. How did you two meet? How have you influenced each other over the years? Are you still close?

JONATHAN COULTON: We met in college freshman year and have been friends ever since. I think we’ve always shared a comic sensibility, and a kind of friendly competitive spirit when we’re cracking jokes in a group of people. He raises the game of everyone he works with. He took the quit-your-day-job plunge long before I did, and it was certainly inspiring to watch him build an entertainment career around himself.

ROOFTOP: How did your family feel after you graduated from Yale, packed up your six string, and moved to New York City to become a singing and songwriting comedy star? Are they supportive of your work?

JONATHAN COULTON: Yes, they’ve always been very supportive. I don’t think anyone thought I was going to Yale in order to do anything in particular – that’s the nice thing about a liberal arts education, it’s ultimately kind of useless so there’s no pressure. So when I meandered through my 20s and finally ended up writing software that was fine, and when I left that to do something else that was fine too. I’m very lucky to have had people around me who believed I could make this thing work.

ROOFTOP: One of the biggest leaps in a budding comics career is ditching the day job and turning pro. What made you quit your job as computer programmer and officially “go for it”?

JONATHAN COULTON: It was a combination of things. I had been performing with John Hodgman on his book tour and also pushing my own stuff out there a little more, and I had gotten enough positive response to think there was a market for what I was doing. I also had just become a father for the first time, and that was a wake-up call – it truly felt like the last possible chance to do something crazy like this. It also felt important to set a good example for my daughter, to be the kind of person who wasn’t afraid to take a chance and do something rewarding.

ROOFTOP: What inspired you to write a song a week for a year?

JONATHAN COULTON: I had just left the job and found myself with a lot of time on my hands. I didn’t want to fritter it away. I also wanted to pretend it was my job to write music for a while to see how that felt, and the best way to do that seemed to be to promise something on the internet. Once I had a regular deadline, it was harder to flake out.

ROOFTOP: They Might Be Giants, Ben Folds, Tim and Eric, Beck, Weird Al, Stephen Lynch, Jonathan Coulton are all names that come to mind when you think of artists that have successfully merged music and comedy. Who are your biggest comedy influences? Your biggest musical influences? Biggest musical comedy influences?

JONATHAN COULTON: I’ve always been a huge Steve Martin fan – I’m particularly amazed at the breadth of his career, how he keeps moving from one thing to another. I think David Letterman is a genius, and I used to watch him when his show was on at 11 in the morning. I love the way he continually breaks the fourth wall, always calling attention to the stuff that goes wrong. Musically, Weird Al and TMBG for sure (it’s obvious, I steal from them all the time), but also Loudon Wainwright, who writes funny songs that are also sad enough to make you really uncomfortable.

ROOFTOP: What are you listening these days?

JONATHAN COULTON:There’s not a lot of new music in my life, I think that’s a function of my age. I spend a lot of time going back over Steely Dan and Pink Floyd and the Beatles. But most recently I fell in love with a band called Tally Hall, really well-produced encyclopedic pop that sounds like it was a lot of fun to write and record.

ROOFTOP: What’s next for JoCo?

JONATHAN COULTON: Who knows! Right now my concert DVD is out and being sold in various retail and online establishments. It’s called BEST. CONCERT. EVER. And it’s a show I did in San Francisco. It’s great to finally have a definitive live version of some of these songs, because the songs are often very different from the recording. I’m also pretty proud of the live show, it’s something I’ve been working on for the last couple of years, and it’s almways really fun.

Catch Jonathan Coulton LIVE:

September 26th. The Paradise. Boston, MA

October 8th. The Ark. Ann Arbor, MI.

October 10th. Park West. Chicago, IL.

October 23rd. Beachland Ballroom. Cleveland, OH.

October 26th. Guthrie Theater. Minneapolis, MN.

For more tour dates, downloads, and an overall good time, visit www.jonathancoulton.com

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