During the postwar period, KGO radio in San Francisco syndicated a Bob Wills & His Texas Playboys show recorded at the Fairmont Hotel. Many of these recordings survive today as the Tiffany Transcriptions, and are available on CD. They show off the band's strengths significantly, in part because the group was not confined to the three-minute limits of 78 rpm discs. They featured superb instrumental work from fiddlers Joe Holley and Jesse Ashlock, steel guitarists Noel Boggs and Herb Remington, guitarists Eldon Shamblin and Junior Barnard and electric mandolinist-fiddler Tiny Moore. The original recorded version of Wills's "Faded Love," appeared on the Tiffanys as a fairly swinging instrumental unlike the ballad it became when lyrics were added in 1950.
Still a binge drinker, Wills became increasingly unreliable in the late 1940s, causing a rift with Tommy Duncan (who bore the brunt of audience anger when Wills's binges prevented him from appearing). It ended when he fired Duncan in the fall of 1948. Having lived a lavish lifestyle in California, in 1949 Wills moved back to Oklahoma City, then went back on the road to maintain his payroll and Wills Point. An even more disastrous business decision came when he opened a second club, the Bob Wills Ranch House in Dallas, Texas. Turning the club over to what was later revealed as dishonest managers left Wills in desperate financial straits with heavy debts to the IRS for back taxes that caused him to sell many assets including, mistakenly, the rights to "New San Antonio Rose." It wrecked him financially.
Wills continued to tour and record through the 1950s into the early 1960s, despite the fact that Western Swing's popularity even in the Southwest, had greatly diminished. Even a 1958 return to KVOO where his younger brother Johnnie Lee Wills had maintained the family's presence. They became the flagship for a station that was hungry for the type of music they played at that time it was called Country Jazz but eventually became known as Western Swing. Wills was now so popular that he bought himself a flour mill and went into direct competition with his former boss.
He kept the band on the road into the 1960s at times the band numbered 40 members they were the first country band to use Drums and Electric instruments They also included jazz hooked up with fiddles and yodelling.
After two heart attacks, in 1965 he dissolved the Texas Playboys (who briefly continued as an independent unit) to perform solo with house bands. While he did well in Las Vegas and other areas, and made records for the Kapp label, he was largely a forgotten figure — even though inducted into the Country Music Hall of Fame in 1968. A 1969 stroke left his right side paralyzed, ending his active career.
He starred in 26 Western movies and was inducted into the Country music hall of fame in 1968. 1969 saw the state of texas give him a special citation.
Hits included San Antonio Rose, Lone Star Rag, Take me Back to Tulsa, Cotton Eyed Joe, Cherokee Maiden, Milk Cow Boogie Roly Poly,
Fortunately for us Wills's musical legacy, endured. His style influenced performers Buck Owens and Merle Haggard and helped to spawn a style of music now known as the Bakersfield Sound (Bakersfield, California was one of Wills's regular stops in his heyday). A 1970 tribute album by Haggard directed a wider audience to Wills's music, as did the appearance of younger "revival" bands like Asleep at the Wheel and the growing popularity of longtime Wills disciple and fan Willie Nelson. By 1971, Wills recovered sufficiently to travel occasionally and appear at tribute concerts. In 1973 he participated in a final reunion session with members of some the Texas Playboys from the 1930s to the 1960s. Merle Haggard was invited to take play at this reunion. The session, scheduled for two days, took place in December, 1973, with the album to be titled For the Last Time. Wills appeared on a couple tracks from the first day's session but suffered a stroke overnight. He had a more severe one a few days later. His musicians completed the album without him. Wills by then was comatose. He died on May 13, 1975.