From the Yale Whiffenpoofs to the Internet, Jonathan Coulton reflects on his career, including his breakout song about a sad software developer.

Question: How did you get into comedy songwriting? 

Jonathanrn Coulton: Well, I've always been interested in music. I played rninstruments when I was young and sang when I was young and was in the rnband and the chorus in school. And I think somewhere in high school I rnhad decided that I actually wanted to make a profession out of it and rnbecome a professional musician and then didn't do much about that for rnmany years. And, you know, like many people, went to college because rnthat's what you do. Then some point after college, found myself in New rnYork City, not really knowing exactly what I was doing there and had a rnfew short-lived jobs and put a band together kind of but never really rndid anything with it. Played out a few times for our friends and rnultimately found myself working in the software industry writing code rnfor a company in New York and did that for about nine years and kept rndoing music on the side, recording things and writing things, just for rnmy own amusement mostly. 

Question: How did a cappella rnaffect your songwriting? 

Jonathan Coulton: It is truern that I was in the Whiffenpoofs in college and before that the rnSpizzwinks. Those are two of the oldest all male a cappella collegiate rnsinging groups in the world. So, very proud to be a part of them and thern Whiffenpoofs really were kind of one of the reasons I wanted to go to rnYale. My dad went to college there and my grandfather went to college rnthere and so, when I was growing up, they both had old records, rnWhiffenpoofs LPs that they would play for me. So I was familiar with rncollegiate a cappella music in a way that many American kids were not. 

Irn was thinking recently some friends of mine from the a cappella rncommunity who I had been out of touch with for a while, recently came torn one of my shows in New York for the first time and as I was doing my rnstandard Jonathan Coulton show, I was thinking of them in the audience rnand I realized how much my shtick on stage really does owe to whatever rnit was that I learned when I was doing a cappella. Because, you're in rnthis group of people and for me it was a group of 14 guys all wearing rntuxedos and you're standing in a big circle and you're singing, you rnknow, ironic covers of popular songs, but also sort of jazz standards. rnAnd there's a mix of stuff that you're really quite serious about. rnYou're serious about the music but you're also wearing a tuxedo and rnwhite gloves and a white tie. It's ridiculous, you know. And you're rndoing a lot of funny stuff in between the serious stuff and it's very rnshtick-y and hammy. So I think I actually took a lot from that. I mean, rnthat's how I learned to be a person on stage. And so that still applies rnto what I do in my show even though I'm now a rock star. I don't wear a rntuxedo anymore. 

Question: One of your first breakout rnsongs was “Code Monkey.” How much did that come out of your life at thatrn time? 

Jonathan Coulton: "Code Monkey" is a rnsong about a sad software developer. It’s loosely autobiographical. It rnis true that while I was working there I felt some frustration about notrn having allowed myself to pursue what I believed was my true calling. I rnwas there for nine years and it wasn't a terrible job. I actually liked rnit quite a bit. I learned a lot. I had fun and good people there. But rnthere was that vague dissatisfaction. So I used that when I wrote the rnsong, but it is loosely autobiographical. The guy in the song really, rnreally hates, really, really hates his job, and in particular, his boss.rn I did not hate my boss. I loved all of my bosses and they were never asrn boring as I described them in the song. I'll say that for them.