Every night, dozens of musicians compete for the title of town troubadour in Chicago. Some strum guitars in dark and dingy bars, others on even dingier street corners. Train platforms, parks and porches all serve as stages, but the spotlight tends to be elusive.
"About a decade ago, I made one of my goals to play at Schuba's," he says. "I've played there three times now, and it's helped convince me that what I'm doing is worthwhile."
It's not the beer talking: The tavern has helped launch the careers of many musicians, from Modest Mouse to My Morning Jacket. Now Reeb is taking his act to watering holes across the Midwest, for a dizzying 15 shows in 23 days. He'll visit Madison for the first time on Tuesday, Jan. 8, when he plays the Frequency.
"I realized I'd rather be poor and playing music than stable with insurance but stuck in front of a computer," he says of his career change.
This epiphany didn't happen overnight. It's taken years for Reeb to believe that his songs deserve the limelight. Glowing reviews from the Chicago Tribune and AmericanaRoots.com helped, as did careful observation of other performers.
"For a lot of artists, it comes down to fear," he says. "It's not whether they write a good song; it's about whether they believe it's worth putting out there."
Battling other forms of darkness has also been essential. When writing songs, Reeb often thinks about a John Steinbeck novella called The Red Pony.
"It captures how life can be wonderful at one moment and terrifying the next. A lot of my songs have a dark side like that, or are about something beautiful that was lost. But they're also about realizing that this beauty was worth [experiencing], even if the story doesn't end happily."