Everyone at the Texas Lone Star Heritage Fest in Austin came to see Okkervil River, according to a friendly woman in her late 20s. She had loved the band since college, when a crush gave her a copy of their breakout 2005 album Black Sheep Boy. But she wasn't smitten, the gesture failed. She used the CD to flirt with another guy.

On stage, New England-bred songwriter Will Sheff looks like a more confident version of that scorn collegiate suitor. Crisp tan slacks hug a tiny waistline, thrift store chambray hangs loosely, a muppet mop of hair brushes over his glasses. He moved to Austin in the late '90s to start Okkervil River, then left for Brooklyn in 2006. He's toured the world, but still seems at home on the outside stage at Stubb's, where his five-piece band delivers their signature self-aware style of sad bastard music. Half the songs appear on their forthcoming album Away, the rest are fan favorites rearranged to sound less noisy and more meditative.

"I looked inside my heart and realized that I didn't really care about rock and roll that much anymore," Sheff tells me the following night in Dallas. "What you're doing in music, if you really boil it down, it's a healing job. The kind of healing that rock offers is catharsis. You rage and scream and pump your fist and you get it out. But it comes back."

Okkervil River tearing through their set at Stubbs.

My task was to find out what's left after the rage runs dry. I'd ride with the band from Austin to Dallas, gain their trust, and unpack Sheff's leftover demons in an attempt to decontextualize his artistic intentions and embarrass him deeply.

Psych! This wasn't a gotcha mission, although at times it felt like one because Sheff acted so alarmingly candid. He's charming in a way that makes you uneasy to share quotes like "music is the air that I breath" or personal details about his 40th birthday plans to take a shit-ton—strike that—a regular amount of psychedelics.

These are the juicy details a caffeinated musician shares when you're riding shotgun in his spacious, Xbox-equipped rental van. Sheff doesn't usually drive, but for these four Texas shows he saves money by serving as Okkervil River's defacto tour manager. The band lounges across three bench seats, smartphones out, earbuds in.

In exchange for my navigational support, Sheff explains:

How to convert a bedroom into a practice space (flip your air mattress against a wall)
When he lost faith in the industry (after a failed four-year struggle to release an electronic album)
What the end of the hard-partying spectrum looks like (waking too hungover to write)
And why artists shouldn't move to New York ("It's like Trump University, you're paying a whole bunch of money and not getting an education")

Will and Ben making the most of their three-hour drive.

We drive pass weird IH-35 landmarks like the Monolithic Dome Institute with Sheff's old iPod providing the soundtrack. He refuses to upgrade the ancient piece of technology for fear of losing hundreds of themed playlists that he uses "medicinally." The current playlist, titled "Hanging in the Van With The Band" ranges from deep indie cuts like "I Could've Just Died" by The Rock*A*Teens (Sheff blogged 1500 words about it here) to "Super" by MF DOOM (who he calls "the Donald Barthelme of rap").

Halfway through the three-hour drive we pull into the Czech Stop, the most notable destination in a century-old ethnic enclave called the "Czech Belt." Once inside the adorable bakery-cum- convenience store, the band scatters and Sheff waits in line to order kolaches. I head to the restroom and drummer Cully Symington steps to the urinal beside me. "I fucking hate this place," he confesses. "Every band I've ever toured with has stopped here."

Ben and Sarah embracing the vibe at Czech Stop.

Despite his cynicism, Symington tears into a jalapeno sausage kolache. Everyone's more talkative after the snack. The iPod plays "Sara," an '80s mega-ballad by Starship, which excites keyboardist Sarah K Pedinotti. Sheff laments that there aren't any good songs with his name, but bass player Benjamin Lazar Davis reminds him of "Willy O' Winsbury," an English ballad about a noble lady impregnated by a commoner.

"Caucasian soul, that's my pleasure center," Sheff jokes, but the song fits with his lyrical style: confessional, analytical of society, a mix of highbrow and lowbrow.

We finally arrive at the hip Deep Ellum neighborhood and find the band's next tour stop, Dallas's Bomb Factory. It's like a high school gym painted jet black with two massive namesake torpedoes at the entrance. Backstage is a playground of amenities including Ted Nugent pinball, a popcorn machine, and a laundry room. A giant eight-foot mirror ball sits abandoned in the corner.

The band soundchecks, nailing haunting harmonies while a billboard-sized screen behind them shows Wimbledon tennis and Taco Bell commercials. Thankfully, we don't run for the border for dinner, instead walking in 95-degree heat to Pecan Lodge, which Texas Monthly named one of the state's four best barbecue joints in 2013.

Sarah has a moment with the Bomb Factory's disco ball.

Everyone digs into fatty brisket and the conversation turns to '90s swing bands. There's consensus about Brian Setzer's guitar chops, and a debate over which Daddies wrote "Zoot Suit Riot" (it's Cherry Poppin', not Big Bad Voodoo). Will Graefe, a jazz guitarist who goes by the name "College Bill," mentions the Royal Crown Revue. Pedinotti remembers that Andrew Bird played in Squirrel Nut Zippers, who Sheff appreciates for their reverence of '30s jazz. I scribble in my notebook a working subtitle: "In Defense of Squirrel Nut Zippers".

With stomachs full of barbecue, Sheff and I head back to the cramped green room for chat. He sits on the couch next to a cheap lamp with the yellowest tungsten bulb and I ask if he wants to lay down like it's a therapy session.

At times the interview feels like one. He talks about his grandfather's passing and how touring affects his girlfriend of nine years, but mostly he explains his music, and how a directionless collection of personal songs became an Okkervil River album.

"It's really important to me to remember that I didn't start making art to get approval from people or make money. I started making music as a compact between me and the creative spirit or whatever, and I need to keep that in mind, always. Getting to do art projects periodically that have nothing to do with furthering my career is a sacrifice you make."

That meant he could barely justify buying a 12-string guitar for $300, let alone renting a recording studio for a month to record what became the band's seventh album Away, which comes out this September. Instead, he recruited a dream team of jazz and avant garde players who could nail the songs in two days. He loved playing with them so much that he decided it was the next incarnation of the band. The new Okkervil River lineup debuted in Austin, playing unheard songs from Away and mellower versions of hits like "For Real" and "Unless It's Kicks."

A pensive backstage chat with Will Sheff.

"I know some people want to hear songs the way they remembered them. It's tough because as a performer, you're an asshole if you're not giving the audience what they paid for. But you're also a phony if you're not feeling it. It's like faking an orgasm," says Sheff.

He believes the audience is the most important part of the show and keeps a journal of every tour date, noting details ranging from the crowd's energy to the venue's layout. He doesn't return to clubs that aren't a good fit. In the future, he might avoid the Bomb Factory.

I was excited to see the band for the second night in a row, partly because Sheff gushed so much about their musicianship.

"These guys are so fucking good. I sit there on stage and it sounds like I put on a record that I've never heard before, but I instantly know is going to be one of my favorites. These guys are just making art, pulling it out of thin air," he says.

Ben and his bass loading in at the Bomb Factory.

But not everyone at the Lone Star Heritage Fest in Dallas came to see Okkervil River, according to an older man wearing Tommy Bahama. The crowd skewed preppier, older, more stereotypically Texan than the 30-something hipsters and young emo revivalists at Stubb's the night before. The main draw on the four-band bill is Shovels & Rope, a duo that sounds like early White Stripes with a Carolina twang.

The band huddles in a circle at the side of the stage, then they put their hands together and Sheff jokingly says, "It's time to bomb at The Bomb Factory!"

And bomb they do! The soundcheck didn't catch a severe buzz that ruins the soft textures of opener "Okkervil River R.I.P." Sheff's acoustic guitar feeds back when he leans too close to the mic. The band expertly mixes Springsteen Americana and Fleetwood Mac grooves in an indie rock blender, but "it's just not what I want right now," says a man holding a $5 Lone Star tallboy—the same beer that price checked for $4 in Austin. Even as Sheff leaps onto the drum riser, people turn their back to the stage, chat loudly, check their phones.

Okkervil River onstage in Dallas.

The band closes with "Black Sheep Boy" to scattered applause. I high five everyone backstage, but it's clear that the show went poorly. No one is upset, it's more like a troubleshooting situation. I'd like to have listened to their conversation, but chicken out and head to the alley to bum a cigarette (sorry mom!).

The band members follow, decompressing behind the club, when a young couple with X'd hands approach to ask for signatures. No one has a Sharpie. Sheff heads back inside the venue while the rest of the band makes awkward small talk with the underaged pair.

Okkervil's music brought them together, they say, and they listened to it constantly for the first year of their relationship. These kids seem to have the type of love that only exists before you're legally allowed to drink, a harsh contrast to the jaded woman I met in Austin who'd regifted Black Sheep Boy.

A minute later Sheff is back, holding a black marker.