Jonathan Coulton is the Contributing Troubadour for Popular Science magazine and the musical director for John Hodgman’s Little Gray Book Lectures. His songs about vengeful nerds, ennui-afflicted clowns, self-loathing giant squids, and devotees of a certain Swedish prefab furniture store are insanely clever without ever being too clever for their own good. 

They repeatedly lure you into laughing before suddenly breaking your heart. And the sick part is, you keep coming back. Coulton's is the voice of every spooky elementary school kid who could never quite keep his shirt tucked in or shoes tied; every lovelorn mason and mad scientist; every one of us who has ever sat despairingly on the floor, surrounded by parts of an Ikea endtable, weeping over our allen wrenches.

For the past year he has been recording and publishing a new song every week as a free podcast called Thing a Week. This rate of output wouldn't be so astonishing if the songs weren't so constently well-written and produced. A few of these songs have become full-fledged internet smashes: his folky cover of Sir Mix-a-Lot's "Baby Got Back," a visual ode to Creative Commons called "Flickr," and of course "Code Monkey," the anthem of software designers everywhere. But it's the less obvious ones that sneak up on you and punch you right in the chest - the song about George Plimpton that makes you want to get out there and do something that really matters, or the song about an office crush that you're certain was written about you and that girl you keep meaning to ask out on a date.

A fully independent musician with the heart of a geek, Coulton has pioneering plan to make a living as a niche artist. He's passionate about Creative Commons, and releases all his music under a CC license that allows for file sharing and copying, as well as non-commercial derivative works. And his community of fans has rallied around him to generate airplay on hundreds of podcasts, create a library of music videos, and even set up gigs through Eventful.com.