In 1969, Ray Benson and Lucky Oceans (Reuben Gosfield) co-founded Asleep at the Wheel in Paw Paw, West Virginia, and soon after they found themselves opening for Alice Cooper and Hot Tuna in Washington, DC. A year later, they moved to East Oakland, California at the invitation of Commander Cody and His Lost Planet Airmen. After being mentioned in Rolling Stone magazine by Van Morrison, they landed a record deal. Their debut album, Comin' Right At Ya was released by United Artists. Soon after, at the request of Willie Nelson, they left Oakland for Austin.

Asleep at The Wheel has recorded with greats Merle Haggard, Willie Nelson and Lyle Lovett. and some of country's young lions like the Dixie Chicks, Tim McGraw and Lee Ann Womack, some pop stars", including Shawn Colvin, the Squirrel Nut Zippers and fellow country preservationists such as Dwight Yoakam.

In February 2009, Ray Benson collaborated with Willie Nelson to release Willie and the Wheel. The long-overdue concept album, originally suggested by producer Jerry Wexler, teamed Nelson and Asleep at the Wheel on several well-known Western Swing selections. Paul Shaffer and Vince Gill also perform on the album. Willie and the Wheel was nominated for a 2010 Grammy Award for Best Americana Album.