Ride with Bob: A Tribute to Bob Wills and the Texas Playboys is the 15th studio album and second tribute album by American country band Asleep at the Wheel. Recorded between June 1998 and March 1999 at studios in Austin, Texas and Nashville, Tennessee, it was produced by the band's frontman Ray Benson and released on August 10, 1999 as the band's only album on DreamWorks Records. The album is another tribute to the music of Bob Wills and His Texas Playboys. Following the critical and commercial success of 1993's Tribute to the Music of Bob Wills and the Texas Playboys, Benson and Asleep at the Wheel decided to produce a second album composed of recordings made famous by Wills. As with the first album, Ride with Bob features a wide range of guest performers, including featured vocalists such as Don Walser, Reba McEntire and Willie Nelson. The album was Asleep at the Wheel's last to feature pianist and fiddler Chris Booher. Ride with Bob was a commercial and critical success. The album reached number 24 on the US Billboard Top Country Albums chart – the band's highest position since 1987's 10 – as well as giving the group its debut on the Top Heatseekers chart at number 15. It received mostly positive critical reviews and was nominated for seven Grammy Awards, three of which it won (for Best Recording Package, Best Country Instrumental Performance and Best Country Duo/Group Performance). Background Asleep at the Wheel decided to record a second Bob Wills tribute album for a number of reasons, including the induction of Wills and the Texas Playboys into the Rock and Roll Hall of Fame in 1999. According to the band's frontman Ray Benson, though, the album "is as much about giving the young guys a chance to record these songs as it is about keeping Bob Wills' music out there," referring to the featured artists who took part in the album's recording. Explaining that the original plan in 1993 was to release a four-album set, he noted that "The passage of six years' time has been really a blessing because we've got a wider variety of people, a whole other generation of country musicians, and a broader sampling of what Western swing was." Speaking about the featured artists, he added that "My idea on [Ride with Bob] was to draw attention to Asleep at the Wheel and Bob