Waylon Jennings once described his second #1 country hit “I’m A Ramblin’ Man” as his “‘bubblegum”’ country song, pretty close to rock and roll in his view. Ray claims that when there wasn’t sufficient material on the radio, he’d just write something. For “I’m A Ramblin’ Man,” Pennington tried to put in a few big cities and some areas of the country that he especially liked.
Every time he would see his friend Waylon Jennings, Waylon would tell Ray how much he liked the song and what he had done with it on his record. In 1967, Pennington changed the arrangement, downplaying the blues element, and put out his own recording on Capitol Records, taking it to #29 on Billboard’s country singles chart. He even told Pennington that someday, he was going to record it himself. That promise went on for nearly seven years, but the time finally came for Jennings to make it come through.
A few months before, on Waylon’s previous album “This Time,” he got entangled in a controversy by recording the material at a different studio owned by Tompall Glaser, and RCA had refused the masters, saying it will inflict damages to the company’s relationship with the electrician’s union. Later on, the label came to an agreement and solved the issues. In addition, they accepted the masters for “This Time,” and even allowed him to record most of his follow-up album “Ramblin’ Man” at Glaser Sound Studio as well. Eventually, the title track was laid down at RCA.
“I’m A Ramblin’ Man,” buoyed by Dave Kirby’s snappy lead guitar, reached the #1 plateau on Billboard’s Hot Country Singles chart on September 28, 1974. The song also generated the first of several disagreements between Waylon and the Country Music Association. On October 14, 1974, Waylon was set to perform on the CMA Awards telecast, where he was nominated for “Male Vocalist of the Year.” The day of the show, producers told him he’d have to cut his performance of “I’m A Ramblin’ Man” down to two minutes. Concerned that an abbreviated version would “damage the song,” as he put it, Jennings walked off the set. Never mind that the tune had already peaked at #1 a couple of weeks earlier, so what damage could a shortened performance have done? He never offered an explanation, but Waylon was Waylon, and he could be quite difficult at times.