The music they produced in Tulsa is nothing short of extraordinary. To the standard string band rhythm section of fiddle, bass fiddle, acoustic guitar and banjo, he added a steel guitar, an instrument used by popular bands in Fort Worth. He also added a piano, which some of the Fort Worth bands were doing too. Then, he did what was previously unthinkable and added drums. Having broken the logical boundary line between him and other string bands, he went on and added a horn section. He may not have been the first to include horns, but he was the first to give them prominence in Western Swing.

As they perfected their sound in Tulsa, Bob’s band used one trumpet, one trombone, and one saxophone. Pretty soon he added a standard electric guitar and, later, he added more horns and gave the Texas Playboys a “big band” dimension during that era in U.S. musical history. Initially, the Tulsa-era band consisted of about a dozen pieces, which gave Bob an immense amount of flexibility and the thing he craved in music more than just about anything: freedom.

The early recordings from the Tulsa years were remarkable. The very first Texas Playboy record was made in September 1935 in a Dallas warehouse under the direction of legendary recording supervisor Art Satherley. The song was a maniacal fiddle tune called “Osage Stomp,” featuring a sassy fiddle lick followed by two loud thumps by the entire rhythm section. The exuberance and abandonment were unlike virtually anything being recorded at the time. Bob plays a long section of the melody—the listener can nearly always tell it’s Bob playing if he isn’t calling out to the other musicians—then he finishes and goes to his famous “holler,” introducing and encouraging the other players.

Bob would break meter in his playing, which led some “legitimate” musicians to think he didn’t know enough about music to adhere to the time signature of a piece. Breaking meter, holding notes longer than the ordinary number of beats in a measure or playing more notes before the ordinary end of a passage and what should have been the beginning of the next verse, were common to blues and other music played by people who nearly always learned songs by ear. Musicians with formal training and at least an elementary knowledge of music theory often thought such practices were evidence of ignorance. Bob and many other players who broke meter did it because it was expressive. Musicians who wanted to play with Bob had to know how to hang in there with him while he held passages.

For instance, listen to Bob’s vocals and stirring fiddle duet with Jesse Ashlock on “Sittin’ on Top of the World” from their September 1935 recordings. The fiddle duet is so relaxed it’s almost languid, but it keeps the beat and the mood of the song. It’s a great example of how the blues treats hard luck with the ironic mischief of somebody used to dealing with whatever life brings along. With all his troubles and the fact that his lover has left him, he can still say, “I don’t worry. I’m sittin’ on top of the world.”