Bob Childer's Gypsy Cafe

2023 Gypsy Cafe raises $50,597 for Oklahoma’s music safety net!

Temps weren’t the only thing soaring in Stillwater on May 7th! More than 800 attendees gathered across five venues to hear 75 Oklahoma songwriters perform song swap sets that blew us away! From an emotional presentation of the Restless Spirit Award to Jake Flint’s family to a packed house at the inaugural White Buffalo Brunch, the festival also raised more than $50,000 for Oklahoma music creators in need!

Thanks to our committee, sponsors, venues, artists, volunteers and everyone who came out to make #gypsycafe possible! 

Restless Spirit Award 2023: Jake Flint

At the Grand Casino Stage at Outlaws, the Restless Spirit Award honoring Jake Flint was presented to his widow, Brenda Flint, alongside his family. Later in the evening, the guitar painted above by artist, Nathan McCray, was sold in a live auction for $8,000 to support the Red Dirt Relief Fund. 

Flint was a red dirt songwriter who played regionally, recorded four albums throughout his career and was named “Breakout Artist of the Year” at the We Are Tulsa Music Awards in 2019. He was a longtime friend to many of the musicians on this year’s lineup and beyond, as well as a loyal supporter of the Red Dirt Relief Fund. Flint performed at Gypsy Café three times and produced livestreams of Red Dirt Relief Fund events and festivals during the pandemic when events could not be done in person. Flint tragically died in his sleep a few hours after his wedding to Brenda in November 2022.

The Restless Spirit Award is given by Red Dirt Relief Fund in recognition of a musician who has impacted the Oklahoma music community in a spirit akin to Bob Childers, a prolific songwriter and the so-called godfather of red dirt music. Previous honorees include Jimmy LaFave (2017), Brandon Jenkins (2018), Randy Crouch (2019), Steve Ripley (2020), Jim Paul Blair (2021) and Chad Sullins (2022).

A round of applause for our partners!

past Gypsy Cafe


Take a trip down memory lane and check out some of our past festivals and their highlights.

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