His first local band was a short-lived, bombastic rock group simply called Mason, featuring brother Matt and a hotshot session drummer. The band's management, which at the time was hard at work launching Kid Jonny Lang, apparently hoped to exploit the Jennings' prodigy appeal in a similar fashion. But Jennings grew dissatisfied with their contrivances and the band fell apart.
After the fallout, he spent another three years in obscurity, recording Mason Jennings--an eight-song concept CD based on his travels in California--and releasing it in 1998. The disc, on which he recorded all the parts, was ignored here for months and, according to Jennings, received "65 vicious rejection letters" from record labels large and minuscule. After months of revolving drummers (Jennings is something of a dictator when it comes to band politics), he settled on Skoro and Stock to carry out his musical ideal. Twenty-five shows later, Jennings is happy enough with his progress that he's no longer even seeking a record contract--at least not this millennium.
At 11 o'clock Jennings, Stock, and Skoro emerge from the 400 Bar's basement to stand before the packed room, and all past struggles are forgotten. Jennings is a relaxed yet animated performer, and the fans filling the first several rows of the audience seem to have some visceral connection to the stream of words coming out of his mouth. It soon becomes apparent that the songs on Mason Jennings are but a fraction of his best work. During the paranoid, apocalyptic "Godless" ("I'm not conquered/Even as the helicopters come for me") or the explosive "Ease Your Mind," Jennings lurches into a trademark maneuver: He turns to profile, raises a bony knee high off the floor, and projects a kick in Skoro's direction. Skoro plays off the bandleader, almost like a smaller version of Semisonic bassist John Munson.
A quick survey of the floor reveals appreciative--even glassy-eyed--female spectators as well as hearty, male-bonding types. During the sublime refrain of the Buddhism-inspired "Darkness Between the Fireflies"--"the past is beautiful like the darkness between the fireflies"--a distinctly female chorus emanates throughout the club, drowning out the lead singer. But the male voices, for the most part, hold out for "Joy." As the show closes, Matt Jennings, who quit music to work toward his doctorate in history at the University of Minnesota, joins his brother on vocals for one raucous number, "The Bike Song." Its complete, unabridged lyrics: "This is a song about ridin' bikes/Drunk as hell/Late at night." It's a brother thing, evidently.
Two days after the show, the band is already in the midst of preparing for its final pair of regular 400 Bar shows, and Jennings sits at a Kenwood deli reflecting upon a lifelong musical pursuit that's just beginning to reap dividends. The band is wisely quitting its 400 stint to avoid a rut and work on developing a regional following. It's a welcome step forward for a musician who often seems to tread the line between bemusement and existential confusion.
"It's really recent that I've been meeting people I like because of my music, and that's been exciting," he says. "But I'm definitely searching for something. I don't sleep, I've lost a ton of weight, don't eat very much. There are certain times that the music just cuts through, and I break through and see something. I don't know, I'm looking for some kind of truth, I guess. Trying to figure out why everybody's alive. I'm pretty obsessive, pretty kind of crazy."
And here, in this hunger for connection, lies the vague possibility that something could go horribly wrong: An industry suit gets his hands on Jennings. Contractual obligations force Jennings to shave his head and pretend to be a Hare Krishna. Jennings records a Dust Brothers-produced album complete with Beckian breakbeats and becomes a one-hit wonder sandwiched on the radio between Silverchair and Sugar Ray. Or maybe he doesn't. Maybe Mason Jennings would never let that happen.
"I get mail all the time now," he says, "and a lot of the questions people ask me are like, 'There's this one Mason, this folk Mason, and then there's this hardcore Mason on the posters. Which is the real Mason?' And it's cool that you don't know there isn't one. You can't package that."
The Mason Jennings Band plays its last weekly show at the 400 Bar Thursday with special guests; (612) 339-2903.