Before wrestling audiences had ever heard of Billy Gunn, he found some success as a professional bull rider under his real name, Monty Kip Sopp. In his early 20s, he decided it was not the career path he wanted to take and turned to tangling with professional wrestlers instead of bulls.

After a few attempts, WWE hired Billy Gunn and Bart Gunn in 1993. On Road Dogg's podcast, Billy admitted he had no idea what the contract terms were, asking, "Well, I have a job. Do I do this on the weekend?" Vince McMahon assured Billy he would be alright without that other job.

Although they were hired together, Billy and his kayfabe brother, Bart Gunn, weren't siblings. They just clicked while working and traveling well together, and the chemistry they shared off-camera translated to what fans saw when they appeared as the tag team, "The Smoking Gunns."

After "The Smoking Gunns" broke up in 1997, Gunn was repackaged as "Rockabilly" — a puzzling solo gimmick, considering he was a talented star from 1993 to 1997 in the tag team division. Gunn believes that WWE was trying to get him to quit so they didn't have to fire him.

In 1998, Gunn teamed with Jesse James as The New Age Outlaws at WrestleMania 14, taking on Cactus Jack and Chainsaw Charlie in the first-ever "Dumpster Match." While the Outlaws lost, they regained their WWE Tag Team Championship the next night, and their interactive fun with the crowd won over the fans.