For the Red Ants Pants Music Festival, lining up artists is an artform

Steve Earle, with his three Grammy Awards and Americana standards like “Guitar Town” and “Copperhead Road,” doesn’t just show up to perform in a cow pasture in tiny White Sulphur Springs.

There’s an art to getting him there.

Festivals like Red Ants Pants rely on big name headliners to both sell tickets and boost the festival’s reputation, and a lot must come together to land someone like Earle — timing, money, negotiation skills, patience and persistence.

Sarah Calhoun is the festival’s founder and its talent booker. And, just as the last notes from one festival are fading, she starts the tricky business of booking the next one.

There are typically 16 main stage artists to book and 14 on the side stage, and most of them have their own tangled system of agents, management, fees, preferences and tour schedules.

Months ago, Calhoun noticed Earle was putting together a summer tour that included the Calgary Folk Festival in mid-July. Since he was essentially in the neighborhood, as tour routes go, he may as well play Red Ants, too. Calhoun tracked down Earle’s agent, they spent several days negotiating, and now there he is at the top of bill.

“Sometimes the process can be long and nerve-wracking, and sometimes it feels like they fall into your lap,” said Calhoun.

This year’s co-headliners Gillian Welch and David Rawlings did not fall into her lap. She’s been chasing them for years.

“I've been talking with their agent forever, and it's like, nope, not touring, nope, not touring,” she said. “And then this year it was, yes they’re touring. So, I had to increase my budget to swing this one, but it’s going to be so worth it, they’re so legendary.”

Assembling each year’s lineup is something like assembling a jigsaw puzzle, except that the pieces are all flying around at different speeds, in different places, and are different sizes. You can’t place some pieces until other pieces you can’t yet reach are in place, and you don’t get to see the picture of what you’re assembling until you’re done.

“There are so many moving parts, so many middlemen, and talking to management who are managing other gigs and other routing along the tour,” she said. “And there’s the catch-22 of having an offer out for three months on an artist and then be waiting and waiting and you’re trying to form the rest of your lineup, so there’s a lot of sit and wait, and this answer hinges on that answer, and this back-up plan depends on that back-up plan.”

The degree of difficulty is compounded by the nonprofit festival’s mission to curate diverse lineups that include plenty of women, artists of color, and LGBTQ artists. And those artists must appeal to the festival’s regular fanbase, a super-chill mix of everyone from cowboys, to college kids, young parents with kids, and boomers in Birkenstocks.

Whatever the secret formula is it’s been working for Red Ants, which has survived longer than many festivals.

Dwight Yoakam and Emmylou Harris have headlined the festival, and so has Tanya Tucker, the Mavericks, Merle Haggard, Wynonna Judd and Lucinda Williams. In 2011, Jerry Jeff Walker, Guy Clark and Rodney Crowell all played on the same bill with headliner Lyle Lovett.

And some of the up-and-coming artists, who Red Ants has a knack for spotting, have done pretty well for themselves since playing the festival. In 2014, Jason Isbell and Brandi Carlile shared a bill with headliner Charley Pride, and since then have piled up a total of 17 Grammy Awards.

Turnpike Troubadours played an early slot in 2017 for a crowd that mostly hadn’t heard of them. Last summer, the band played for 75,000 people in a Texas stadium.

It helps that Calhoun has been assembling the puzzle for 15 years. She’s well connected with artist agents from across the U.S. and Canada, and she attends conferences where agents pitch artists and new artists perform. Calhoun has been so knocked about by some of those lesser known artists, like William Prince, Lindi Ortega and Kaitlin Butts, that she’s found a spot for them at Red Ants, helping to boost their careers.

And those are usually the artists Red Ants fans go home buzzing about. As a fan, it’s one thing to see someone as legendary as Gillian Welch. It’s another to spot the next Gillian Welch.

This year, the buzz is building for Stephen Wilson Jr., who plays the main stage at 8:30 p.m. Friday, July 25. The 45-year-old former boxer quit his corporate job to be a songwriter and earlier this year released his first full-length album, which already has 60 million plays on Spotify.

Wilson, who describes his style of music as “Death Cab for country,” is bound for glory and Calhoun spotted him before most of his fans did and had to have him for Red Ants.

“He’s one that as soon as he was on our radar we wanted to get him here,” she said. “He has exploded and is just so hot right now, and so good, and hasn’t really done much in Montana before. He’s right on the cusp, and we got him.”