A Ride With Bob is the first-ever musical drama about the life and legacy of Bob Wills and his Texas Playboys starring nine-time Grammy winning Ray Benson and Asleep at the Wheel.

The play focuses on a conversation between Benson and Wills about the trials and tribulations of being a working musician. In 1973 after the release of the band's first album (which paid tribute to the music of Bob Wills), Benson was invited by his idol to Dallas for a meeting. Upon his arrival, he learned Wills was not feeling well and the meeting was postponed for the next morning. That same night Wills had a stroke and went into a life-ending coma.

In A Ride with Bob, he finally gets to have his conversation with the Spirit of Bob, who visits him on the Asleep at the Wheel bus late one night. The fascinating and sometimes outrageous stories of Wills' career, his contribution to American music, and his raucous personal life unfold. The drama includes performances of Wills' most famous songs, including "San Antonio Rose," "Faded Love," "Cherokee Maiden," "Take Me Back to Tulsa," and many more.