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

Jason Isbell, Elizabeth Cook, Randy Houser and more on how the 'Late Show' changed their lives

David Letterman has been a longtime champion of Jason Isbell's music. Credit: Jeffrey R. Staab/CBS via Getty Images

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.

"He loves songs, he loves story songs and he loves songwriters," says Isbell. In turn, the Late Show helped boost musicians within the Americana genre to degrees most artists can't measure: There's the fiscal bump, which often translates to a speedy jump in album sales, but it also represents a sign of approval that makes somewhat esoteric acts instantly more digestible and approachable by the public at large. "It's helped the genre find a home, because it put that kind of music in middle-American households for the first time," Isbell adds, "and had a lot to do with bringing Americana music to the forefront. I can't think of anybody else who has done that."

Well, except for maybe Isbell. It's no coincidence that the same could be said about the Southeastern singer himself, who has been a leader of the genre and one of few artists to develop a friendship with the prickly host. Letterman, historically, hasn't cared to bond or buddy up with many guests. He's known as a rather elusive figure, and most musicians who appear on the show make their first, and only, point of contact with Letterman at the handshake moment once their song is complete (as opposed to Jimmy Fallon, who is known to pop his head into dressing rooms and say hello).

But he found kindred spirits in Isbell and Cook, the latter of whom he first heard on SiriusXM's Outlaw Country station, during his regular drives into the city from his Connecticut home. While Fallon makes viral videos with Justin Timberlake, Letterman was asking Isbell and Cook for just one more Van Zandt song. More than championing roots, Americana and folk, what makes the Late Show stand out is that it's always been booked from a place of taste, not trends.

"I think his team is very in-tune with what he likes, more than just chart watching," says Carla Sacks, president/founder of PR firm Sacks & Co, which has been responsible for numerous genre-spanning Letterman bookings over the years, including Emmylou Harris, Sturgill Simpson and Chris Stapleton. The buzzed-about Stapleton was the last artist to debut on Letterman before his closing weeks. "Letterman has made a statement of bravery in their bookings and trusting their instincts," Sacks says.

Since the show's debut in 1993, Letterman has indeed made a point of choosing artists that didn't always play to a radio-friendly, Top of the Pops mentality: Steve Earle, Harris, Zevon, Willie Nelson and Tom Waits were all early favorites, with Ryan Adams and Dawes joining the ranks. Of course, there's Cook, who was virtually unknown to the pop masses when she made her debut on the show, and chatted with Letterman on the couch for nearly ten minutes. Beyond just being a fan of the genre, he and his bookers, Sheila Rodgers and Sheryl Zelikson, come more from a place of personal taste and instinct — rather than looking at the Top Five slots on the Billboard chart and saying, "Let's book those."

"Even before there was a designated Americana genre, Dave liked American guitar rock," says Cary Baker, president of Conqueroo, another publicity firm that has booked many appearances on the Late Show, including, most recently, Billy Joe Shaver. "He was the first to book R.E.M., who sang 'South Central Rain' from Reckoning in January 1984. He was also an early champion of Miracle Legion, Golden Smog and Syd Straw."

Letterman also has chosen, along with his trusted team, musical guests who had absolutely zero promotional tie. Take this past December, when he asked Dan Penn, the singer-songwriter, to play the show after he heard him on SiriusXM. "He booked him without a current album, without a tour, with nothing specific to promote other than it caught his interest," says Jeremy Tepper of the satellite radio network's Outlaw Country station. The same timeframe of the Penn appearance, Fallon hosted Nikki Minaj, Lady Gaga and Foo Fighters. Even back to the first few weeks of the Late Show in 1993, musical guests were Robert Plant, John Hiatt, Patti Smith, Johnny Cash and Billy Joel. Chart leaders at the time? UB40.

It's also important to note that Americana, and singer-songwriters, aren't always "happy" brands of music, and Letterman has never been scared to push sensitive performances and stripped-down moments that put the lyric at the forefront. "He's not afraid to have really sad songs on a show that is supposed to be pure entertainment," says Isbell. "He's able to have someone on there who is just heartbreaking after he's just talked to Jerry Seinfeld."

The final weeks of the Late Show have seen Letterman giving the stage to all of his favorites —  the Avett Brothers and Brandi Carlisle playing the Carter Family classic "Keep on the Sunny Side," in addition to Swedish sister-folk duo First Aid Kit, Dawes, Isbell, Waits and Adams. On May 2nd, Rodney Crowell, Harris, Steve Martin and Amos Lee played, on his request, "Will the Circle Be Unbroken," one of the pivotal songs that made a young Letterman fall in love with roots music.

"Here is a man with a huge stage, and he wants to bring his audience fresh considerations," says Cook, who describes the importance of her relationship with Letterman as "off the charts. "Everybody else is serving bananas. Dave is serving papaya á la Townes Van Zandt. Unheard of from places as high on the totem pole as the Late Show."

In an era where MTV is free of actual music, and YouTube is loaded a mile a minute with clips made both in the bedroom and the soundstage, late night has proven to be an important curatorial gauge when it comes to artist discovery. So the fact that the Late Show has taken such an aggressive point of view in showcasing Americana, country and roots artists has proven to be a crucial boost to a flooded market. Letterman, points out Americana Music Association executive director Jed Hilly, was likely the first person to even reference the actual term "Americana" on-air.

But Letterman isn't Americana and country's only foothold in the late night arena. Conan O'Brien, since making the move to TBS especially, has also been a champion. Conan's booker, Jim Pitt, is a former Nashvillian with a strong penchant for the genre. "[Conan] has worked Americana into its musical mosaic from day one," says Cary Baker. "Pitt is a huge fan of Americana and other forms of good music and deserves credit right alongside Letterman."

It's not yet clear what the Stephen Colbert blueprint will look like once he takes over the Late Show, but it is rumored that Zelikson might have some kind of role in the future booking team. On The Colbert Report, he did make an effort to weave music — from Cheap Trick to Wilco — into a program that, as a satire, didn't always lend itself to live performance. Whether or not Colbert's history as a staunch liberal will impact the role of country music on his show, Houser isn't too worried. "He's a smart guy," he says. "And he has fans to think about."

As for Letterman, the void will certainly be a palpable one — both in the stories he squeezed out of guests on his couch, and the stories he let songwriters share on the musical stage.

When it comes down to it, he's a diehard groupie in cargo shorts who ended up hosting a television show.

"I think Dave is just like many," says Cook. "A music fan that has been displaced."