Each week, the latest honoree is revealed on CMT Hot 20 Countdown .
Wills formed his band, the Texas Playboys, in 1934 and set to work pioneering a sound that mixed the contemporary music of his day — big band, jazz and early country music. Performing on radio shows and at dance halls around the country, his popularity rose throughout the ’40s until the advent of rock ’n’ roll.
Wills’ hits include “New San Antonio Rose,” “New Spanish Two Step,” “Roly-Poly” and “Stay a Little Longer.” He is frequently credited as a catalyst for the Bakersfield Sound popularized by artists like Buck Owens, Merle Haggard and Wynn Stewart. He was also one of the first major artists to use electrified instruments and drums, helping to set the stage for country music’s expansion into the mainstream.
In 1968, Wills was inducted into the Country Music Hall of Fame, and in 1999, he and the Texas Playboys became members of the Rock and Roll Hall of Fame.
Wills passed away in 1975.
“Yeah, he kind of created western swing music,” Strait said of Wills. “When we were playing the honky-tonks and bars in Texas, we could do four hours of swing — nothing but Wills’ stuff — and did a lot of times.”
Strait said the western swing tradition lives on through bands like Asleep at the Wheel.
“We still have Asleep at the Wheel around, and I’m a big fan of theirs,” he admitted. “They’re keeping that music alive, for sure. Ray Benson’s is such a fun music, that if you never heard it but if you listen to it, you’re hooked.”
For Benson, Wills showed that boundaries in music are meant to be broken.
“Obviously, Asleep at the Wheel took off from Bob Wills,” he told CMT during the poll. “How can I explain that? This is one of the most charismatic, amazing performers that the world has ever seen. And this is not from me — because I never saw him play live. He was before my time. Got to meet him once, but never saw him perform. But I’ve talked to dozens of people and seen the films, and the guy was just charismatic — like you couldn’t take your eyes off of him.
“He was outrageous, and he pranced around,” Benson said. “And he was theatrical, and he hollered ’Ahhhh!’ and people we’re going ’Who is this guy?’ And he had the best musicians in the world. I mean, this was one of the great bands of all time.
“I don’t mean to drop names, but one time I was with Clint Eastwood and we were talking about Bob Wills. He said, ’Ray, I saw Bob Wills when I was 19 years old.’ … Clint Eastwood is a big jazz fan, loves jazz piano, and he said, ’I really didn’t want to see no cowboy band, but I heard they were having some pretty girls down there, so I went down there, and those guys could play.’
“That was the deal,” Benson continued. “They wore cowboy hats, they played string instruments instead of trombones, saxophones and trumpets, but they played swing music and blues and jazz right. I love Bob Wills. Country music would be very different had Bob Wills not shown up because he brought drums, he brought electric guitars … when most of the country acts were doing hillbilly acts basically. In fact, drums weren’t allowed on the Grand Ole Opry until the ’70s. So Bob Wills and his Texas Playboys are No. 1 on my list.”
Dunn agreed, praising Wills’ courage to be different.
“He was innovative in that he took a big band sound and put a western sound to it,” Dunn said. “They just dressed it up, put cowboy hats on and gave all the lyrics western flavor. It takes courage to step off, and I’m sure at first that they were kind of criticized. It takes a good bit of artistry to step off and follow something different and follow through with it and make it happen.”
Tune in to CMT Hot 20 Countdown each Saturday at 11 a.m. ET/PT to check out the next artist on CMT All-Time Top 40: Artists Choice .