Jonathan's father is a lawyer. Jonathan's affinity for music, though, was apparent from the beginning, since he played the snare drum in his high school marching band.
Jonathan's interest in music bloomed at Yale, where he studied music in pursuit of his Bachelor of Arts degree. There, he also joined a capella music groups the Spizzwinks(?) (the parenthetical question mark is part of the name) and the Whiffenpoofs. Also while at Yale, Jonathan met John Hodgman, a friend who became integral to his development as a performing musician.
After graduation, Jonathan and John Hodgman moved to Manhattan. Jonathan worked for some time in the Artists and Repertoire (scouting) department of an adult contemporary record label. Next, he worked for some time at the William Morris Talent and Literary Agency.
Jonathan then found a job as an espresso slinger at Cooper's Coffee, where he later began to perform music. When Cooper's closed, Jonathan moved on to a software company called Cluen. He was employed there for the next eight years, where he wrote computer software.
During this period of relative stability in Jonathan's life, he undertook a few projects. The first was an album called Smoking Monkey, and was released in 2003. A modest number of copies were sold. Jonathan notes:
I didn't sell very much stuff as far as I remember, maybe a couple CD's a month, but at this point it really wasn't so much about making a living. Mostly it was a nice ego boost to have an actual CD, and to see my name come up in the iTunes store. 
Around that time, John Hodgman sought Jonathan's collaboration on the Little Gray Book lecture series, a project John described as a two-man-one-man-show. The lecture series was similar to Hodgman's later book tour. Other than banter between John and Jonathan, John would deliver a monologue and Jonathan would play accompaniment or perform works composed for the show.
During one of the Little Gray Book lectures, Jonathan was approached by the curator of the Pop!Tech conference, Andrew Zolli. Andrew, upon hearing Jonathan perform "The Future Soon", invited Jonathan to come play "The Future Soon" at Pop!Tech. On October 17, 2003, Jonathan did perform at Pop!Tech. Attending Pop!Tech turned out to be a large factor in Jonathan's current career. Here, Jonathan was introduced to Creative Commons, the license under which Jonathan releases his music to this day. Also, Jonathan began discussions for the idea of becoming Contributing Troubadour for Popular Science magazine (which was employing John Hodgman).
During the course of Little Gray Books, Jonathan completed his album Where Tradition Meets Tomorrow. He released the album on October 1, 2004.
In February 2005, Jonathan was officially placed on the masthead of Popular Science magazine with the title of Contributing Troubadour. As contributing troubadour, Jonathan wrote and recorded the EP Our Bodies, Ourselves, Our Cybernetic Arms as a downloadable supplement for the issue of Popular Science entitled, "The Future of the Body."
On September 2, 2005, Jonathan quit his computer programming job at Cluen. This marked the beginning of Jonathan's professional music career.
Soon after resigning, Jonathan began creating his first albums as a professional musician. Based on an idea proposed by a co-worker, Jonathan started on the Thing a Week project. During the year-long project, Jonathan created and released one new song each week for a year. The project started September 16, 2005 and ended on September 29, 2006. The project yielded the four Thing a Week albums comprising the Thing a Week box set.
Jonathan started the PopSci Podcast on May 12, 2006, producing some of the earlier episodes concurrently with the later songs in Thing a Week. He hosted the podcast until Episode 37 on May 21, 2007.
In a May 2011 interview on NPR's program Planet Money, Coulton revealed that online sales from his website had topped one million dollars.
- Bio on the Jonathan Coulton website
- "Don't Quit Your Day Job" on the Jonathan Coulton blog
- "Work vs. Play" on the Jonathan Coulton blog
- "How I Did It" on the Jonathan Coulton blog