CAJUN GEMS: Ben Whitesides (left) and Darrell Bourque.

Ben Whitesides is thinking. Glancing down at my tape recorder, sipping from a small cappuccino, the 31-year-old singer/songwriter rolls up the sleeves of his green hoodie before composing his thoughts. “I’ve struggled with the whole idea of canning it all,” he says, exhaling a bit now that he’s said it. “Music is the thing I’ll love the most forever, but it’s kind of miserable to be in this place of terminal indecision. It’s basically just thinking too much about it—when you think too much about it, you get in trouble. You should just do it off the cuff.”

Whitesides is talking about Cajun Gems, his recently reformed outfit with friend and bassist/drummer Darrell Bourque that played their first proper show in two years this fall. We’ve been chatting for two hours at a booth in Southeast Portland’s Beulahland, and Whitesides has been incredibly candid about everything—growing up on the East Coast, his insecurities, the job market, the Joggers (his other, more widely known band) and why it’s so hard to finish a song. But suddenly Whitesides becomes careful with each word.

I was hesitant to call the Joggers my favorite Portland band until I heard the first and only Cajun Gems record. A handmade, well-worn disc Whitesides and Bourque made “purely for the fun of giving our friends CDRs” in 2001, it sealed the deal. Richard Byrd at Little America has the same charm as the early, pre-Matador Guided by Voices records. It’s a loose collection of wilted pop songs, recorded straight to crappy mics on a barely functioning, ancient Mac laptop in the basement and bathroom of Whitesides’ old Northeast Portland house. The record’s finest moments sound like Joggers songs in utero; perfectly minimal with only a guitar, simple drum line, cheap, buzzing keyboard and Whitesides’ nasal drawl/croon. Stripped of most of the Joggers’ intersecting, winding guitar leads, “Double Cowlicks” and “Homebody”—the latter of which utilizes a finger-picked guitar tuned to resemble a banjo, and a sighing, ascending slide lead—push his fragile voice and elliptical lyrics to the forefront.

“If I’m honest, it’s probably the thing I’m most proud of,” Whitesides says about Richard Byrd. “I was younger in years, and to be frank, less jaded about things. It’s obviously played by people who are amateur musicians but are also enthusiastic, and I hadn’t heard a lot of bands that were doing finger-picking and drums and I liked that.”

After burning 100 silkscreened copies of Richard Byrd, Whitesides decided to put most of his focus into his other band. The Joggers took a template—jittery, ornery indie rock not too dissimilar from the Walkmen or the French Kicks—and made it majestic. Adding occasional four-part harmonies (five years before Fleet Foxes made Glee Clubs cool again) to Whitesides’ unabashed love of math rock band Polvo and its weirdly dissonant guitar tunings, 2003’s Solid Guild and its followup, With a Cape and a Cane, are woefully underrated records. Their songs don’t build as much as they ascend from twisting, labyrinth riffs, steady basslines and dancey, quilt-pattern drums from Jake Morris. And despite its complexity, the band is far from arty—every dense layer and winding scale attacks in tandem with infectious hooks and profoundly catchy melodies. The appeal is endless, and the Joggers should have been Portland’s next big thing, only one thing got in the way: Whitesides’ second-guessing his own talent.

“I can’t put words into Ben’s mouth, but if I were to guess, experiencing the beginnings of success was so jarring that it eventually became a kind of pressure on all of them that just didn’t feel natural,” writes Chantelle Hylton via email. Hylton—now booking at New York’s Knitting Factory after years in Portland—helped the Joggers (then called Stateside) by continually booking them at her club, the Blackbird, in the early aughts. “I think they should have been the ‘next big thing’—but even that, the ‘next big thing’ language, is a part of that industry that I think kept them from wanting to go there.”

The Joggers’ reluctance to embrace the promotional cycle—Whitesides says the band was never excited about the touring life—combined with Whitesides’ lack of urgency, led to a shaky few years for the band. To compound the problem, the Joggers’ label, StarTime—originally run by Isaac Green, a friend of the band—was bought out by Vagrant Records (a subsidiary of Universal). The band and label were mutually unhappy until the Joggers left in 2006.

“One of the things that helped us be more productive when we were first starting out was that we had an outside force,” Whitesides says. “And those deadlines can be really useful if you’re a band that is prone to thinking too much and self-doubt and second guessing.”

After touring on StarTime’s With a Cape and a Cane, the band recorded “four or five songs” that no one was really stoked on. Instead of trying to make a push, Whitesides—hindered, in part, by the lack of a label or imposed deadlines—dithered for most of the year, and by the end of 2007 the petered-out Joggers were thinking about calling it a day. The only reason the band remained active this year was two irresistible offers: the chance to tour with Stephen Malkmus and the Jicks in the spring and a slot opening for Whitesides’ idol Polvo during its reunited MFNW gig.

The band’s recent material sounds destined for greatness, but Whitesides has since retreated to his old habit of endlessly revising Joggers songs. “He has a long process from inception to completion of a song,” offers Tim Putnam, singer for the Standard and founder of Partisan Records. “But it’s one of the reasons his body of work is so engagingly complex while sounding effortless.”

Amid false rumors of the Joggers’ breakup, Whitesides recently began focusing on the Cajun Gems for the first time in years. Armed with a huge batch of songs, built from “days’ worth of riffs and rifflettes” on his computer, Whitesides is now readying tracks for both the Joggers and the Cajun Gems. He confesses to never really liking the Gems’ live sound, but with a reconfigured four-piece lineup—Chris Pickolick of Book of Maps sits in on guitar/keyboards and Pan Tourismos’ Brandon Clemens is on bass—that might change. And after three years of dormancy, 2009 could be a breakthrough for Whitesides: Partisan Records plans to release a new Joggers split 7-inch with Pan Tourismos and a new Cajun Gems album.

“There’s this quote from Lou Barlow that I love,” Whitesides says. “He said, ‘My only talent is that I can finish songs.’ And I don’t think that’s true in his case, but that sentiment, I really believe that one of the hardest things, for me at least, is to sign off on [a song]. There’ll be things you like about it and things you don’t like about it—but if you can’t be at peace with it, you can’t move forward.” Even if one of his two bands never becomes the next big thing, you can’t fault a man for not trying.