“I’m a Ramblin’ Man” is a song written by Ray Pennington. He recorded the song in 1967 for Capitol Records. It was later performed by American country music artist Waylon Jennings. The song was Jennings’ second number one on the country chart and stayed at number one for a single week. With a slightly more commercial sound than some of his recent records, The Ramblin’ Man remained true to Jennings’ outlaw country image and uncompromising musical vision. 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. Actually the tune started out more like “back-porch blues,” songwriter Ray Pennington’s description of a style patterned after R & B legend Jimmy Reed. Pennington, who was working for King Records in Cincinnati when he wrote the piece in the mid-1950s, built it specifically for a band he was moonlighting with. 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. Ray was enamored with West Virginia and he was living in Cincinnati. He also thought of Chicago as a swinging place and he got all of those geographical locations in there. In 1967, Pennington changed the arrangement, downplaying the blues element, and put out his own recording on Capitol Records. 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. He even told Pennington that someday he was going to record it himself. That went on for nearly seven years, but the time finally came for Jennings to make good on his promise. Waylon Jennings and Ray Pennington found themselves in RCA’s Studio A on February 8, 1974 preparing for a session. Pennington had brought along “I’m A Ramblin’ Man,“ which Waylon was planning to cut, but Ray had another tune with him that enamored Jennings even more called “Oklahoma Sunshine.” That was the one Jennings really wanted, so he made a deal with Pennington that if Ray would let him have “Oklahoma Sunshine,” he would also record “I’m A Ramblin’ Man” and have Pennington serve as producer. Ray agreed and Waylon cut both songs that day. A few months before, on Waylon’s previous album “This Time,” he had stirred up controversy (which he was pretty good at) by recording the material at a different studio owned by Tompall Glaser, and RCA had refused the masters, suggesting it would cause problems for the company with the electricians’ union. Eventually, the label solved the issues and accepted the masters for “This Time,” and even allowed Waylon to record most of his follow-up album “Ramblin’ Man” at Glaser Sound Studio as well, although 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