Guitarist, singer, and songwriter Billy Ray Reynolds of Mount Olive arrived in Nashville in the 1970s, just as the “outlaw” movement in country music was beginning. He made his mark as bandleader for Waylon Jennings and later by playing with Jennings’s group The Highwaymen alongside Johnny Cash, Willie Nelson, and Kris Kristofferson. He enjoyed a long solo career as well, and his songs have been recorded by artists such as Jennings, Cash, Tanya Tucker, Conway Twitty, and Toby Keith.

Born on October 6, 1940, and raised in the Saratoga community near Mount Olive, Mississippi, Billy Ray Reynolds discovered his passion for country music at nine years old during the Jackson stop of a Grand Ole Opry touring show featuring Hank Williams. This early inspiration laid the foundation for a remarkable career as a central figure in the outlaw country movement, a group of artists who defied Nashville’s polished sound and image. After releasing a handful of solo singles on the Epic label, in 1970 he brought his guitar playing and songwriting skills to Waylon Jennings’s backing band, the Waylors, and played an integral role in establishing the group’s driving sound. Reynolds recorded with the Waylors on several of Jennings’s landmark albums and wrote the songs “Sandy Sends Her Best” from Lonesome, On’ry and Mean, “High Time (You Quit Your Lowdown Ways)” on Dreaming My Dreams, and “Cloudy Days” and “It’ll Be Her” on The Ramblin’ Man.

In 1976, Reynolds left the group to focus on songwriting, a decision that led to a prolific career spanning more than three decades. His compositions have been recorded by a wide range of country artists, including Johnny Cash, Toby Keith, Tom Jones, Conway Twitty, Bobby Bare, and Alison Krauss. One of his most notable songwriting successes came in 1975, when Tanya Tucker turned his song “Don’t Believe My Heart Can Stand Another You” into a top-five hit on country radio. Three years later, Cash included “It’ll Be Her” on his album Gone Girl, further cementing the song’s legacy. The song became one of Reynolds’s most-recorded works, with additional renditions by Tompall Glaser and Debbie Boone, among others.

Reynolds’s songwriting credits extended to Southern rock, as well. Dickey Betts of The Allman Brothers Band popularized “Atlanta’s Burning Down” and “Dealin’ With the Devil” during his years fronting Dickey Betts & Great Southern. Other artists, including Barbara Fairchild and Gary Stewart, also recorded his songs, and David Frizzell charted with “Country Music Love Affair” in 1985. “Billy Ray always showed you his real voice,” Nashville journalist and Country Music Hall of Fame and Museum executive Peter Cooper once told a documentarian. “He sang like he talked, and he wrote like he thought … what he came up with was exactly Billy Ray Reynolds.”

In addition to his musical achievements, Reynolds acted in television series like In the Heat of the Night and I’ll Fly Away, and landed small roles in feature films such as John Grishman’s The Rainmaker and the 2013 adaptation of William Faulkner’s As I Lay Dying. Often cast as a villain, Reynolds brought a rugged authenticity to his roles, further underscoring his connection to the outlaw image. After decades as a sideman, Reynolds finally released his debut solo album, Whole Lot of Memories, in 2003, featuring duets with Merle Haggard and Bonnie Bramlett. Six years later, he returned to Mount Olive but continued to create and perform music until his death in 2019.