Bayless was born as John Edward Bayless II in Oklahoma City, Oklahoma. His father, John Sr., immediately began calling him Skip – his father also had called his mother Skip, as in skipper of the ship. The name stuck, and Bayless was never called John by his parents. He eventually had his name legally changed to Skip. His parents owned and operated the Hickory House restaurant in Oklahoma City, which specialized in barbecue. Bayless worked in the restaurant in his youth, but never considered it as a career path.