WITH APOLOGIES to the dime store tuxedo and top hat of Dr. Demento, there is little hope for novelty music. "Weird Al" Yankovic's career is a true anomaly, and for every parody he willed onto the pop charts, there are myriad contributions to the wacky music canon that time mercifully forgot ("Fish Heads" anyone?). Other rare exceptions—namely Loudon Wainwright III and They Might Be Giants—never settle for swapping punchlines for choruses, instead they balance humor with heartbreak, all while distancing themselves from the radio host that demands we all "stay demented."

Jonathan Coulton is far from demented. If anything, the former software writer turned reluctant musician is steeped in logic, hyperaware of his role as a onetime internet meme and singer on the comedic fringes of pop music. Much like his acronym-heavy peers LWIII or TMBG, Coulton walks a fine line as both a heartfelt troubadour and the finest voice of the everyone's-a-comedian YouTube movement.

Preceding such memorable online musical memes as "Chocolate Rain" and Keyboard Cat, Coulton's music first found an audience via forwarded emails and message board postings that sung the praises of a man who could soundtrack the prideful geekdom of the dotcom generation. Proof of this can be found in his tour schedule, which always seems to favor cities with open WiFi networks. "Generally a good gauge for how big the audience is going to be is what percentage of the commercial sector is involved in the tech industry," says Coulton. "Anywhere there's a bunch of nerds, there's going to be a big Jonathon Coulton audience."

Prolificacy is not an issue that ails the Brooklyn resident. In his vast catalog, Coulton's range extends from the wonders of inexpensive Swedish furniture (on "Ikea" he sings of a store that sells "furniture for college kids and divorced men"), to a cubicle-dwelling computer programmer in "Code Monkey" that nurses a dead-end job and an equally futile infatuation with the office receptionist (sort of like The Office from the perspective of the IT guy who never gets Pam Beesly).

"This is very cliché for an artist to do a bunch of things, get some recognition, and then resist the labels they've been courting all their professional lives," Coulton explains. "At the same time, it's true there's another side of what I'm interested in and the thing I love about They Might Be Giants, and Loudon Wainwright as well, is that there's this union of funny and sad. When it hits you in the right way, it's a really powerful thing, because you're listening to this music and it's funny, it's making you laugh, and then the third or fourth time you listen to it you realize it's actually incredibly sad. That turnaround moment is to me what it's all about."

This dichotomy is best experienced in moments from his live collection (Jonathan Coulton Unplugged) where he emotionally gushes about the parental pangs of a newborn changing his life ("You Ruined Everything") before seamlessly segueing into a song about a giant squid racked with guilt about its wanton destructive ways ("I Crush Everything"). Coulton's year-long "Thing a Week" project found the Yale graduate penning a new song weekly, eventually compiling all 52 in a four-volume box set. Coulton self-releases his albums and takes pride in existing off the crumbling music industry grid, even if that means having to do his own books.

"[In the music industry], you could be a crazy, creative person who liked to party, wrote fantastic songs, and trashed hotel rooms, and you were allowed to do that because there was this whole business engine behind you supporting that," explains Coulton. "But I can't afford to get drunk and trash hotel rooms. I have to update Quicken."