Prior to his musical career Holyfield was a wholesale appliance salesman and advertising account manager.
[3] In 1972, Holyfield left Arkansas and moved to Nashville, Tennessee, to pursue a songwriting career and his first song was recorded in 1973.
He received his first number one hit with "Rednecks, White Socks and Blue Ribbon Beer".
[4] In addition to his collaborations with Williams, Holyfield's songs have been recorded by numerous Nashville singers including George Strait, Reba McEntire, Barbara Mandrell, Kathy Mattea, Tammy Wynette, Conway Twitty, Charley Pride, Randy Travis, The Judds, Mark Chesnutt, John Anderson, Mel Street, Gary Allan, Johnny Rodriguez, The Nitty Gritty Dirt Band, The Oak Ridge Boys, Ernest Tubb, Anne Murray and Charly McClain.
He has been a member of the board of directors of the Nashville Songwriters Association International, (NSAI) for almost 25 years.