Bob Childers' Gypsy Cafe festival to celebrate Oklahoma musicians, honor Jake Flint

STILLWATER — John Cooper had no idea how his life was going to change 12 years ago when he helped organize a gathering of his fellow Oklahoma musicians at The Farm, the Stillwater homestead recognized as the birthplace of Red Dirt music.

What started out as a 2011 musical reunion for the filming of a Red Bull mini-documentary has spun off the nonprofit Red Dirt Relief Fund, which has helped more than 800 Oklahoma music professionals in need over the past decade, as well as the Bob Childers' Gypsy Cafe, the Stillwater music festival that has become the organization's largest annual fundraiser.

"We wanted to come up with a way to be able to help our people in times of need," said Cooper, a member of the Oklahoma Music Hall of Fame band the Red Dirt Rangers.

"I just think this was supposed to happen — and it did. And then it just exploded into this thing that it's become, and it's really cool."

Billed as Oklahoma’s largest homegrown songwriter festival, the 12th annual Bob Childers' Gypsy Cafe is set for May 7 and will feature about 75 Sooner State songsmiths performing acoustic song swaps at five Stillwater venues.

"In some ways, it feels like we just started this yesterday, and in some ways, it feels like a lifetime ago. But it's exciting to see that we have been able to grow this," said Red Dirt Relief Fund Executive Director Katie Dale, who helped organize the first Gypsy Cafe back in 2011.

"We have more stages, new partners ... and we're gonna keep doing it."

More: Red Bull Gypsy Cafe to chronicle red dirt history on The Farm

What's new at the 2023 Bob Childers' Gypsy Cafe?

The acoustic music showcase is named for the late Bob Childers, the Oklahoma songwriter known as the “godfather of Red Dirt music,” and the fanciful nickname for a shed on the grounds of The Farm.

Several changes are planned for this year's festival, including shifting it from a midweek event to a Sunday soiree.

"Sunday opens it up a little bit to more: It's a day off, people are already hanging out. Wednesdays, if you're in the working world and you've got a job, it can be hard to get away to get up there (to Stillwater)," said Cooper, who is on the Red Dirt Relief Fund advisory council after serving for several years on the organization's board of directors.

"Last year was the first year post-COVID that we were able to actually get people together — we went two years doing it virtually — and it was our best year ever by far."

This year's Gypsy Cafe will start at 11 a.m. with a new event: the White Buffalo Brunch at Stonecloud Brewing. An add-on to the festival, the Sunday brunch will include a buffet from local restaurant Good Little Eater, two drink tickets from Stonecloud Brewing and a Red Dirt Rangers set of Childers tunes featuring Randy Crouch, Cody Canada, Carter Sampson, Mike McClure and other guests from the festival lineup.

Tickets are limited and include general admission to all the other festival venues.

What venues are hosting this year's Bob Childers' Gyspy Cafe?

The festival will kick off in earnest at 1 p.m. May 7, with sets of three or four songwriters performing at four venues: Eskimo Joe’s, George’s Stables, the Grand Casino Stage at Outlaws and the Coors Light Stage at The Salty Bronc. Adding the latter two stages puts the Gypsy Cafe back on Stillwater's legendary The Strip.

"The Salty Bronc is a venue that pays tribute to Oklahoma music legends. It's a really beautiful space ... that's fairly new," Dale said. "It's exciting to see that there are these new venues in Stillwater that are prioritizing live music. So, it's kind of having a renaissance."

A free shuttle will run in a loop to the four general admission venues from 1 to 8 p.m. May 7 so ticketholders can catch as many sets as they please.

Who is playing this year's Bob Childers' Gypsy Cafe?

Along with Gypsy Cafe staples like Canada, Sampson, McClure, Monica Taylor, John Fullbright, Tequila Kim Reynolds, Mike Hosty, Bo Phillips and Bryon White, the event will include 10 songwriters making their festival debut.

"We're always looking at who's starting to make waves. Lance Roark is a great example: a young artist out of Tahlequah who just got picked up by ... a big agency and is probably going to take off out of Oklahoma. We're glad we got him before he hits the road off on his career path — and we had that same experience with Kaitlin Butts and Parker Millsap playing this festival," Dale said.

Although its roots are in Red Dirt, its organizers pride themselves on assembling an eclectic lineup of Oklahoma songwriters, which this year includes Beau Jennings, Ken Pomeroy, Jacob Tovar, Cassie Latshaw, Kierston White, Dylan Stewart, Paul Benjaman, Nellie Clay, Gabe Marshall, Joe Baxter, Adam Aguilar and Turnpike Troubadours Kyle Nix and RC Edwards.

"We have a really big umbrella, and everyone is included," Cooper said. "I love the fact that we do the Jimmy LaFave Songwriting Contest that really gives people a chance to shine that are unknown. It's important: You've got to have songwriting contests, you've got to have open mic nights. That's the only way people get in on the ground floor. ... No band ever just stepped on stage and said, 'Hey, here we are' in front of a packed house at Cain's Ballroom. That does not happen. You've got to start somewhere."

Named for an Oklahoma-Texas music icon, the Jimmy LaFave Songwriting Contest is open to unsigned and emerging Oklahoma songsmiths. At 4:40 p.m. May 7 at Outlaws, singer-songwriter and Glenpool Middle School teacher Brent Giddens will be awarded a $600 cash prize along with the titles of overall contest winner and People’s Choice victor for his song “Shades of Texas.” Giddens will perform his song, which was selected out of 68 entries, as part of his set with McClure, Bryon White and Buffalo Rogers.

Along with the performances, the Eskimo Joe’s Main Stage will feature regional vendors and a silent auction of music experiences and memorabilia. Before the family jam finale, the main stage will host at 7:05 p.m. a live auction of a Gypsy Cafe guitar signed by the entire lineup and a live painting by Bobby Moore, a member of the Tulsa-based band The Brothers Moore.

How is the Gypsy Cafe honoring the memory of Jake Flint?

The late Jake Flint has been named the winner of the festival's Restless Spirit Award, given annually by the Red Dirt Relief Fund to recognize a musician who has impacted the Oklahoma music community in a spirit akin to that of Childers.

Born and raised in Holdenville, Flint was an up-and-coming talent on the Red Dirt music scene, playing with his band and as a solo acoustic act at venues all over Oklahoma, Texas and surrounding states. The Tulsa-based Red Dirt singer-songwriter released four albums between 2016 and 2021, charted three singles on the Texas Regional Radio Report and was named Breakout Artist of the Year at the We Are Tulsa Music Awards in 2019. 

Flint, 37, died in his sleep a few hours after his wedding in November 2022, a tragedy that sent shockwaves through the Oklahoma music community.

The Restless Spirit Award in Flint's honor will be presented to his widow, Brenda Flint, alongside other members of his family, at 5:40 p.m. May 7 on the Grand Casino Stage at Outlaws.

"Jake was very important to this cause. He not only jumped in to help the Red Dirt Relief Fund in so many ways — every chance he could, he always offered his help — but he also did that for other fellow musicians, many of whom are on this lineup," Dale said. "So, it just felt like the right thing to do, to really take a moment to celebrate him, his legacy and the friendship and mentorship and kindness that he extended to so many in the music community in Oklahoma."

How do you get tickets to the Bob Childers' Gypsy Cafe?

The Bob Childers' Gypsy Cafe is the flagship fundraiser for the Red Dirt Relief Fund, which has provided aid to more than half the artists on the lineup and given grants in excess of $700,000 to music professionals statewide since 2012.

General admission tickets are $30 in advance or $35 the day of the event and $25 for students with ID. A limited number of tickets are available for the White Buffalo Brunch and for reserved seats at the Eskimo Joe’s Main Stage. Those tickets range from $80 to $150.

To purchase tickets, go to https://www.reddirtrelieffund.org/gypsycafe.

This article originally appeared on Oklahoman: Bob Childers' Gypsy Cafe continues to honor, help Oklahoma songwriters