The St. Augustine Amphitheatre is pleased to welcome Leon Brides and Charley Crockett for The Crooner & The Cowboy Tour on September 14, 2025, with special guest Reyna Tropical.

Today, Grammy Award-winning R&B artist Leon Bridges and Grammy-nominated Texas maverick Charley Crockett announce The Crooner & The Cowboy Tour—a series of once-in-a-lifetime shows that celebrate their shared roots, longtime friendship, and the rich musical heritage of Texas

Leon Bridges, known for his timeless storytelling and genre-bending sound, brings the spirit of his acclaimed fourth studio album, Leon, to the stage, alongside a career filled with platinum hits and sold-out headline shows around the globe. From busking on the streets to selling out Dickies Arena in his nagtive Forth Worth, his rise has been nothing short of extraordinary. With his signature smooth vocals and boundless creativity, Leon Bridges delivers a performance that’s as personal as it is powerful.

Charley Crockett, the street busker turned country cult hero turned rising country star, joins as a very special guest, embodying the independent spirit of country music’s great songwriters. A self-made troubadour, Crockett carved his own path, releasing 14 independent albums and headlining legendary venues like Red Rocks, the Greek Theatre in L.A., and the Ryman. His latest record, Lonesome Drifter, out now via Island Records and co-produced by Crockett and Shooter Jennings, channels the raw, unfiltered essence of a road-worn storyteller.

Together, the Texas pair bring their unique yet complementary styles to the stage, alongside their deep and beloved catalogs. This isn’t just a concert—it’s a collision of soul and grit, an evening of music that echoes across time, place, and genre.

TIME: 6:00pm (5:00pm doors)

TICKET PRICE: $56.00 - $153.00 

ON SALE: Friday, March 28 at 10am

TIP: Avoid ticket fees by purchasing tickets in person! The St. Augustine Amphitheatre Box Office is now open Monday - Sunday: 7:00 AM - 5:00 PM. The Box Office accepts credit and debit card payments only.