Name: Asleep at the Wheel
Start: 2025-03-02T19:00:00-05:00
Location: 1051 Main St, The Villages, FL, United States, Florida 32159

For over fifty years, Asleep at the Wheel’s Ray Benson has been traversing the globe as an ambassador of Western swing music and introducing its irresistible sound to generation after generation. More than 100 musicians have passed through the Wheel, but Benson remains the front man and the keeper of the vision, in the process racking up more than 30 albums, ten Grammy awards and literally millions of miles on the road.
“I’m the reason it’s still together, but the reason it’s popular is because we’ve had the greatest singers and players,” Benson explains. “When someone joins the band, I say, ‘Learn everything that’s ever been done, then put your own stamp on it.’ I love to hear how they interpret what we do. I’m just a singer and a songwriter, and a pretty good guitar player, but my best talent is convincing people to jump on board and play this music.”
Asleep at the Wheel has collaborated on records with genre-spanning friends, including Willie Nelson on 2009’s Grammy Nominated Willie and the Wheel and other critically acclaimed artists, including Brad Paisley, Jamey Johnson, Merle Haggard, George Strait, the Avett Brothers, Amos Lee, Old Crow Medicine Show and Lyle Lovett on Still the King, their 2015 critically acclaimed and Grammy winning tribute to Bob Wills. On their latest release, Half A Hundred Years, Asleep At The Wheel continued their contributions to the American music landscape when three original members of Asleep at the Wheel—Chris O’Connell, Leroy Preston, and Lucky Oceans—returned after 40 years to lend their voices and musicianship to a number of tracks on the album along with Emmylou Harris, Lee Ann Womack, George Strait, Lyle Lovett and Willie Nelson.
Asleep at the Wheel represents an important cornerstone of American roots music, even though some of its members and audiences represent a new generation. That far-reaching appeal remains a testament to Benson’s initial vision.
“It took me 60 years, but I’m doing what I’m meant to do—singing and playing and writing better than I ever have. A bandleader is just someone who gathers people around them to play the best music they can play. I just try and make the best decisions possible and kick some ass every night onstage.”
Asleep at the Wheel has collaborated on records with genre-spanning friends, including Willie Nelson on 2009’s Grammy Nominated Willie and the Wheel and other critically acclaimed artists, including Brad Paisley, Jamey Johnson, Merle Haggard, George Strait, the Avett Brothers, Amos Lee, Old Crow Medicine Show and Lyle Lovett on Still the King, their 2015 critically acclaimed and Grammy winning tribute to Bob Wills. On their latest release, Half A Hundred Years, Asleep At The Wheel continued their contributions to the American music landscape when three original members of Asleep at the Wheel—Chris O’Connell, Leroy Preston, and Lucky Oceans—returned after 40 years to lend their voices and musicianship to a number of tracks on the album along with Emmylou Harris, Lee Ann Womack, George Strait, Lyle Lovett and Willie Nelson.