Devon Gilfillian
Photo Credit: @CalQuinn
Devon Gilfillian
Watch the Live at 35 video of Devon Gilfillian
Lily Meola
Southwest: On The Rise to Luck Live
Southwest: On The Rise to Luck Live
The second-annual Southwest: On The Rise To Luck program upped the ante in 2019 with a three-date On The Rise to Luck Live Tour featuring live shows at all three of The Rustic’s locations–Dallas, San Antonio and Houston.
Luck Reunion, presented by Southwest Airlines, selected three artists, Katie Pruitt, Madison Cunningham, and Cha Wa, to participate in the tour through Texas as they vied for a spot to play on Luck’s World Headquarters Stage with help from fan voting on Southwest.fm.
Not familiar with the infamous Luck Reunion? You should be. It’s a rogue cultural collective headquartered at Willie Nelson’s storied private property, “Luck, TX.” The mission of this event is to continue the American Roots narrative by gathering artists and brands who are contributing to creative culture on their own terms. The Southwest: On The Rise To Luck program has shined the Luck spotlight on unparalleled emerging artists, like Devon Gilfillian and Thomas Csorba.
In addition to performing at The Rustic, one artist, Katie Pruitt, was granted a coveted slot and the once-in-a-lifetime opportunity to perform on the main World Headquarters Stage.
Madison Cunningham

Madison Cunningham
Madison Cunningham participated in Southwest: On The Rise to Luck Reunion 2019.
The close circles I run in are made up of people who participate in different sides of the industry - producers, engineers, drummers, bass players, guitar players, song writers, etc: so our home town means something a bit different to each of us. But the obvious thread that binds us together is the same love we share for music that’s alive and honest. I think we’re all constantly aware of the legacy that was born here in LA, and the chance we have to be a part of the legacy that’s currently being born. It can’t help but have an impact on how I write and play, and the way my friends/colleagues write and play. - Madison
Watch the video of Madison Cunningham at Luck Reunion
Cha Wa

Cha Wa
Cha Wa participated and rose to the top in Southwest: On The Rise to Luck Reunion 2019.
From the funk-laced beats and bass-heavy sousaphone blasts that kick off their new Grammy-nominated album Spyboy to the gritty warmth of singer J’Wan Boudreaux’s voice, New Orleans brass band-meets-Mardi Gras Indian outfit Cha Wa radiates the fiery energy of the best features of the city’s street culture. Spyboy was produced by Galactic’s Ben Ellman.
Dating back to the late 1800s, the Mardi Gras Indian tradition began when African-American men first marched in Native American dress through the streets of New Orleans on Mardi Gras day. The tradition, which includes a host of songs shared among the various tribes, has been kept alive for over a century and today is as vital as ever. Mardi Gras Indians have influenced the biggest names in New Orleans music. The most prominent Mardi Gras Indian today is Monk Boudreaux, the Big Chief of the Golden Eagles tribe, and his grandson J’Wan is stepping up with Cha Wa to propel their culture forward.
Watch the video of Cha Wa at Luck Reunion