A few years ago, Brent Stewart arrived at the conclusion reached by plenty of maturing songwriters beleaguered by low-paying gigs and little recognition: it just didn’t seem worth it.

Stewart, a journalist and writer, penned a vast catalog of Americana and rock songs throughout his youth in Murphysboro; in his teens, he founded and fronted the band The Sympathizers.

By the time he moved to Wisconsin after a seven-year stint as a reporter at The Southern, he’d grown disillusioned with the practice of playing original songs to empty rooms for next to no money.

“You get to a point where your passion for it may not equal the level of frustration that comes with it,” Stewart said.

But that passion wasn’t easily stamped out. Stewart drove all over the Midwest to record sessions with the original Sympathizers, a project that grew into a nine-track album called “The Restlessness.” Back in Madison, he crafted “Haze,” a stripped-down, introspective record with dreamscapes that mirror the desolation of Wisconsin in the winter.

Backed by an all-star cast of local players, Stewart will release those two albums at a show at The Varsity Center this Friday.

For Stewart, the release marks a return to his first love of songwriting after a lengthy hiatus.

“I just set it on the shelf because I just wasn’t playing anymore, I just didn’t have the heart to do it. But even when you don’t want to deal with all the frustration of setting up gigs and booking gigs and yadda yadda, it’s still in you and it’s still something that you want to do,” Stewart said.

That desire was made plain when Stewart booked a gig at Big Muddy Brewery last August. He invited Dan Tejada, a guitar player who will join Stewart onstage this weekend, to sit in. Even though they had never practiced, the sets went perfectly; the pair had undeniable musical chemistry.

“It was great, and it was so much fun, and we got paid, and everything just kind of clicked for me, and I thought, you know what? I can do this. I can do it again, and it’s a matter of having the medium between the joy and the frustration, and the joy overwhelming the frustration,” he said.

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Stewart now lives in St. Louis, where he works in marketing. His struggle with how to fit music into his life certainly seeped into his albums, he said.

“It’s kind of a weird bit of synchronicity, because the two albums are similar in a lot of ways, in that the songs that make up ‘The Restlessness’ are kind of about figuring out who you are and who you want to be, and then the songs on ‘Haze’ are more about dealing with who you are, and it’s kind of an interesting juxtaposition in the two,” he said.

On Friday, Stewart will share the stage with Tejada, Kyle Triplett of the Bankesters, Andrew Staff of the Swamp Tigers and Tobias Merriman of the Jenny Johnson Band. Singer-songwriter Tim Crosby will open the show.

Triplett said Stewart’s music evokes a more melancholy version of Darrell Scott or Tom Waits.

“His delivery makes the show interesting, because he's one of the only guys I've met that can smile and laugh while singing heartbreaking songs,” Triplett said. “Also, it's a real treat to get to perform and enjoy this music with such a great band. I've loved picking with Brent from years back, and each of the musicians he's chosen adds their own style and personal brand to the songs.”

“I salute anyone brave enough to write original songs and send them out in the world to be judged,” said Merriman. “It’s a skill I don’t possess, so I’m happy to support Brent in this endeavor, even though I only recently met him.”

Even with two albums freshly pressed, Stewart remains ambitious: he hopes to put out a double LP this fall.

“I figure with the next one, I’ll really get the closet totally cleaned out and be able to have a fresh slate,” he said.

Brent Stewart will perform with special guests at The Varsity Center on Friday from 7:30-9:30 p.m. Tickets are $10 and are available at the door or through Eventbrite.com. Copies of “Haze” and “The Restlessness” will be available for $10 each.

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