Bobby's hometown is Mountain Pine, Arkansas, but he currently lives in Austin, Texas, who for the record has came out gay in his August 16th appearance on the show. His hobbies include shopping, working, working out with his trainer, Ahmad, eating and playing Call of Duty 4 on his Playstation 3. His favorite TV shows are The Office, The Late Show with David Letterman (whom Bobby idolizes and envisions a future career as) and Entourage.

Bobby's first job in radio was at the age of 18 on the college radio station KSWH 91.1 The Switch at Henderson State University. With only a week of experience at The Switch, Bobby landed a job in Hot Springs, AR with KLAZ 105.9 as part-time air talent. During his four-year stint at KLAZ, Bobby was responsible for turning 10 college students into professional broadcasters (most of which worked at KLAZ with Bobby's recommendation). After graduating from Henderson State University in the summer of 2002, Bobby was hired by a Little Rock station, KQAR - Q100, to host "The Bobby Bones Night Show.." Bobby garnered tons of national attention on his show in Little Rock with a stunt where Bobby snuck into a competing station's building to take over their radio waves for over 15 minutes. The act generated buzz nation-wide and also landed Bobby in legal trouble. Even with legal issues on his resume, Bobby was promoted within the company and was offered syndication for "The Bobby Bones Night Show" in Austin, San Antonio, New Orleans, Meridian and Oklahoma City. This market gave Bobby a 3-million listener market nightly. In July of 2003, Bobby was offered to move his show to the west coast for an even larger radio market. Through contract negotiations, Bobby remained in Austin where he now hosts the Bobby Bones Show on 96.7 KISS FM, syndicated in Wichita, KS. On April 25, 2008, Bobby announced to MySpace fans via his blog that the show's contract had been extended by four years.