Bobby was raised in Lessburg, FL.

After graduating high school he went to work with the Art Davis show out of Orlando.

In approximately 1958, Bobby joined the Army and was eventually stationed in Germany. He remained in the service for about a decade and was discharged in about 1968.

After leaving the Army, Bobby returned to Central Florida and worked for a time with Jack and Jerry Calhoun (The Calhoun Twins) out of Kissimmee. They played shows all over Florida, the Southeast and the Bahamas.

During the early seventies, Bobby took a job playing lead guitar for country music legend, Ferlin Husky. At the time he was living with Ferlin and became close friends and running buddy with another country legend, Lefty Frizzell.

As a songwriter, Bobby had several hits, including:
"Shoes" recorded by Ferlin Husky in 1973 and "Chattanooga City Limit Sign" recorded by Johnny Cash in 1981.

Bobby also received a BMI award for his song "Another Chance" recorded by Tammy Wynette.

Bobby got to play on the Grand Ole Opry, which was his childhood dream. Bobby also got to pick with some of his guitar heros such as Billy Byrd, Hank Garland, Phil Baugh & Jim Stafford.

Bobby Drawdy passed away on July 17, 1997, from complications associated with bypass surgery.