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The band moved to Arista Records and released the album, Keepin ' Me Up Nights.
Soon after, the band saw turnover as old members left and new members entered.
In 1991, Ray Benson directed the music and co-starred in the movie Wild Texas Wind with Dolly Parton.
In honor of the 66th anniversary of Route 66, the band launched the Route 66 Tour.
In 1993, the band released the instant hit A Tribute to the Music of Bob Wills and the Texas Playboys to much critical acclaim with several guest musicians.
Two years later, the band celebrated their 25th anniversary by releasing The Wheel Keeps on Rollin.
In 1999, the band and Dreamworks released Ride with Bob, as their second tribute album to Bob Wills.
This album became an instant hit and garnered the band two Grammy wins, one for Best Country Instrumental, and the other for Best Package Design.

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