How David Letterman Built a Late-Night Haven for Country Music

If Jason Isbell ever goes broke, the last few bucks he spends will be a hundred dollars from David Letterman, given to him in cash straight out of the late-night host’s cargo-shorts pockets.

“He told us it was for beer and gas money,” Isbell tells Rolling Stone Country with a laugh, recalling the time Letterman asked him and his band to come to his ranch in Montana to play the small-town Forth of July barbeque. “Though he told me I couldn’t have any beer, since I’d recently quit drinking. The whole time his wife is going, ‘Don’t do that, Dave! You’re embarrassing us!'” Letterman was being a fanboy, basically; of both a musician he loved and a genre — Americana, by proxy, but really the craft of songwriting — he’d come to champion.

This wasn’t the first time Letterman had asked Isbell to play outside of his Late Show stage — though Isbell made his debut as an instrumentalist in Justin Townes Earle’s band, it was his performance of “Codeine,” off 2011’s Here We Rest, that really perked the host’s ears. Letterman asked Isbell to come down to Birmingham, Alabama, where he was overseeing a Habitat for Humanity build. “That night, they wanted to have a party for everyone that worked on the house,” Isbell recalls. “Dave came in, and Paul [Shaffer] sat with us, and we played a bunch of old Muscle Shoals numbers that Dave wanted to hear, and some Elvis.”

Letterman has never been shy with his special requests. Back in 2008, he was riding around on the ranch, listening to country radio, when he came upon the song “Anything Goes” by Randy Houser. He liked the midtempo, pedal-steel-twanged track so much that he had his bookers invite the then-relatively unknown singer on the show — with one slight caveat.

“He loved the second verse of the song so much he wanted to hear it twice,” Houser tells Rolling Stone Country. “The arrangement was literally in Dave’s request. ‘Anything Goes’ was the first single I ever put out, maybe in the fifties on the chart at the time. It doesn’t have to be a big hit — if Dave dig its, he pushes it.” Houser worked on the new arrangement with Shaffer and Letterman was thrilled. “Yeah, that’s exactly what I’m talking about,” he said after the performance, shaking the singer’s hand.

Letterman has always been a repressed musical director, especially when it comes to his beloved artists. In 2013, he asked Isbell to play a cover of Townes Van Zandt’s “Tecumseh Valley” with another favorite, Elizabeth Cook, and, just a few weeks ago, a version of Warren Zevon’s “Mutineer” with wife Amanda Shires. “Once you start talking to [Dave] about Townes and Warren Zevon, you don’t tend to divert from that for a while,” says Isbell. Many hosts could keep preferences this left of the mainstream to themselves, but not Letterman. This was his show and his stage, and the Late Show became a haven for quality acts who didn’t ever need to count a Number One hit as a booking prerequisite.

But really, at Letterman’s core, the genre — folk, Americana, country — is less important than the story. His knack for digging out the unusual tale from his couch-bound guests marks the same exact curiosity that propels his love of songs. Letterman’s a comedian, for sure, but at the center of every good joke, and every good late-night interview, is a story.