Born on This Day in 1933, the Songwriter and Label Founder Who Penned One of Waylon Jennings’ Most Memorable Hits

On this day (December 22) in 1933, Ray Pennington was born in Clay County, Kentucky. He was a singer, songwriter, musician, and producer who worked with the likes of the Stanley Brothers and Hawshaw Hawkins. While he is best remembered for writing Waylon Jennings’ 1974 No. 1 single, “I’m a Ramblin’ Man,” he also penned hits for Kenny Price and others. Additionally, he founded Step One Records, which signed Roger Miller and other A-list acts.

Videos by American Songwriter

Pennington released his first single, “Three Hearts in a Tangle,” under the name Ray Starr in 1958, via King Records. However, he didn’t like how the record sounded. So, he asked that the single be pulled. Afterward, he began working as a producer and A&R person for the label. He produced albums for Hawkshaw Hawkins, the Stanley Brothers, and Reno and Smiley.

[RELATED: On This Day in 2020, Country Music Said Goodbye to the Songwriter Who Penned Hits for Waylon Jennings, Ricky Skaggs, and More]

Three years after he released his first single, Pennington found his first success as a songwriter. According to Music Row, Roy Drusky released “Three Hearts in a Tangle in 1961. It peaked at No. 2 on the country chart. Kenny Price made “Walking on New Grass” and “Happy Tracks” top 10 hits, furthering Pennington’s songwriting success.

Ray Pennington Finds Chart Success, Pens a Classic

In 1966, Ray Pennington signed with Columbia Records. The next year, he released the only top 40 country hit of his career, “I’m a Ramblin’ Man.” It peaked at No. 29 on the country chart. Years later, it would be a much bigger hit.

Waylon Jennings recorded “I’m a Ramblin’ Man” for his album The Ramblin’ Man in 1974. He released it as a single in July of that year, and it quickly became his second No. 1 single on the country charts.

The song only stayed at No. 1 for a week, but it had a lasting impact on Jennigns’ career. It became incredibly popular among fans. Furthermore, he added it to multiple albums. Aside from The Ramblin’ Man, the song appeared on Jennings 1976 live album and his 1979 greatest hits collection. More recently, it appeared on Never Say Die in 2000 and the posthumously released Ultimate Waylon in 2004.

By this time, Jennings had full creative control of his career. As a result, he was allowed to choose who produced his albums. He and Pennington shared production credits on The Ramblin’ Man, which was the most successful album at the time. It peaked at No. 3 on the chart, a feat no other release in his catalog had achieved.

Featured Image by Tom Hill/WireImage