The Wheel Keeps on Rollin' received positive reviews from the majority of critics, many of whom praised its mix of "classic" Western swing and more radio-friendly country music. Some commentators, however, criticised's Benson vocal performances on the record. The album did not chart in the US, but was the band's first to reach the top ten of the RPM Country Albums chart in Canada when it peaked at number 3 in 1996. It was the band's last studio album to feature pianist Tim Alexander.
