What: They Might Be Giants, featuring Jonathan Coulton.
When: 8 p.m. Sunday.
Where: Track 29, 1400 Market St.
Admission: $20 in advance, $22 at the door (ages 14 and up)
Venue website: www.track29.co.
From a giant squid that accidentally destroys the ships it loves to an evil genius who starts a robot war to win over his high school crush, Jonathan Coulton is a champion of creating sympathy for the unlovable.
"That's a very compelling kind of character to me: A monster who is pathetic," the Brooklyn-based singer/songwriter said during a phone interview.
"I struggle, in my own life, to not be a small person, in the sense of pettiness and that sort of thing," he added. "Characters who are that way and who don't really recognize that they are that way or who are that way and are gloriously unapologetic about being that way, I find to be fascinating characters."
In 2005, Coulton left his job as a software programmer and committed to Thing-A-Week, a madcap plan to write and record a new song every week for a year.
In the course of creating witty, story-driven material that put an unexpected spin on science-fiction villains and pop-culture icons, Coulton became an Internet sensation.
Coulton said he traces his success to his fifth entry, a slow, acoustic cover of Sir Mix-A-Lot's "Baby Got Back." The song went viral and drew massive amounts of attention to his work, but he admitted the better part of his eventual success was due to luck.
"The next day, all that traffic was gone," Coulton said, laughing, "but it was definitely a sign to me that what I was doing had some potential.
"I was very fortunate to get that kind of positive response early on. That kept me going in the weeks when I had a somewhat darker take on how things were going."
Coulton's catchy pop songs have wormed their way into high-profile locations and attracted the attention of geek-rock aficionados. "Code Monkey" became the theme song for an animated show by the same name on the G4TV network. "Still Alive," a triumphant anthem by a passive-aggressive, homicidal artificial intelligence, was featured in the hit 2007 video game "Portal."
In 2010, his success landed him several dates serving as an opener for his idols, They Might Be Giants, with whom he will be appearing Sunday at Track 29.
Coulton normally tours as a solo acoustic artist but is accompanied on this tour by a drummer and bassist. Given his perennial feelings of inadequacy compared to "serious" musicians, Coulton said he was initially nervous about fronting a band, but the experience has breathed new life into his back catalog.
"A lot of the old songs were conceived as band songs and recorded as band songs, only with me playing all the stuff," he said. "They spent a few years just living in my acoustic guitar in front of audiences, and now to have them move into this much bigger house of the band and relax and spread out feels really nice."