At the end of World War II, Boots Randolph played saxophone, trombone, and vibraphone in the United States Army Band. After his service in the Army, he played with Dink Welch’s Kopy Kats in Decatur, Illinois, from 1948 to 1954. He briefly resided in Louisville, Kentucky, before returning to Decatur to start his own group. He left Decatur in 1957.

Randolph recorded for Monument Records in Nashville and played on Roy Orbison’s 1963 hit, “Mean Woman Blues.” He was also featured on “Little Queenie” by REO Speedwagon, “Java” by Al Hirt, “Turn On Your Love Light” by Jerry Lee Lewis, and “Rockin’ Around the Christmas Tree” by Brenda Lee. He was present on many recordings by guitarist Chet Atkins with whom he often performed. Early in his career, he often billed himself as Randy Randolph.

As a solo recording artist, Randolph placed four singles in the Top-100 between 1963 and 1967. The most successful of these was “Yakety Sax”, which reached #35 in 1963 and stayed on the charts for nine weeks. Randolph was also successful on Billboard Magazine’s album charts, having fourteen entries between 1963 and 1972. Boots With Strings from 1966 reached #36 and stayed on the chart for nearly two years.

In 1977, Randolph opened a successful club of his own in Nashville’s Printer’s Alley. He also frequently appeared on the television program Hee Haw, and was a member of the Million Dollar Band.

On July 3, 2007, Randolph died at Skyline Medical Center in Nashville, Tennessee, after suffering a brain hemorrhage. He had celebrated his 80th birthday just one month prior. He had a son, a daughter and four grandchildren.