Before he was a musician, singer-songwriter and Internet sensation, Jonathan Coulton wrote software — a career he quit to pursue his current professional full time in 2005. He's the musical director for Little Gray Books created and hosted by friend John Hodgman, and is the Contributing Troubadour for Popular Science Magazine.
Shortly after retiring from his day job, Coulton launched the "Thing a Week" project, producing a new song each week for a year that was released as a free. He reports having been unable to ensnare any girls while playing the snare drum in his high school marching band. This sad state of affairs led him to switch to guitar, and pen a number of bittersweet ballads steeped heavily in teenage angst. He says this didn't work, either.
Now, Coulton revels in his success as the house musician on NPR's Ask Me Another, where he wooed audiences with the following songs, played live during the show's inaugural season. Take a listen!