Kip James was born Monty Sopp in 1963 in Orlando, Florida. He began in the WWE in 1993 as Billy Gunn as one part of the tag team The Smoking Gunns with his on-screen brother Bart. In early 1995, they won their first Tag Team titles after defeating Bob Holly and the 1-2-3 Kid. They held the titles until Wrestlemania 11 when they lost to Yokozuna and Owen Hart btu regaind the titles in September of that year. They had to give up the titles due to Billy needing neck surgery but upon his return, the Gunns won their third tag team title in May 1996 after defeating the The Godwinns. Losing the belts to Owen Hart and the British Bulldog proved to the end of the Smoking Gunns as Billy walked out on the team after their new manager Sunny walked out on them.

He began his singles by renaming himself Rockabilly, a protege of the Honky Tonk Man. He had a short feud with Jesse James but after realizing that their careers were going nowhere, he suggested they start to tag together and Billy agreed by hitting the Honky Tonk Man ove the head with his guitar. The New Age Outlaws, as they were renamed, immediately became a heel team and defeated the Legion of Doom for their first WWE Tag Team Championship. During this time, they began to align themselves to with D-Generation X which became permanment after Wrestlemania 14 when they regained their Tag titles after Mick Foley and Cactus Foley beat them for the titles at Mania. They defended their titles sucessful for months until losing to Mankind and Kane but their won the titles for the 3rd time after winning a handicap match against Mankind after Kane no-showed the match. Their thirdn reign came to an end when they were beat by the Big Boss Man and Ken Shamrock.

The Outlaws started to focus on singles wrestling and Gunn his first singles title after defeating Hardcore Holly for the Hardcore Championship under his name Mr. Ass. At Wrestlemania 15, he lost in a triple threat match to Holly to lose the Hardcore title. He went onto win the King of the Ring and feud with his former partner Road Dogg and The Rock among others. In 1999, the New Age Outlaws reunited and won the title from the Rock N' Sock Connection in September and reunited with the rest of DX. After losing the titles, they won them for the 5th and final time after beating Mankind and Al Snow. They lost the belts to The Dudley Boyz and Gunn went away to recover from an elbow injury.

Gunn returned to the WWE in October 2000 to feud with the Right to Censor, who wanted to censor his "Mr. Ass" name. Gunn and Chyna lost a match to Right to Censor and he had to stop using the Mr. Ass name and changed it to "The One" Blly Gunn. He feuded with the group The Radicalz and beat Eddie Guerrero for the Intercontinental Championship but lost it to Chris Benoit two weeks later. He also won the Hardore title during this time and formed a team with the Big Show called Show Gunns but none of these lasted for long.

In 2001, Gunn began to team with Chuck Palumbo and Billy and Chuck rose to the top of the tag team ranks. They started has a face team but turned heel and began to become increasingly affectionate  toward each other showing evidence of a storyline homosexual relationship. In February 2002, they won their first Tag Team championship They feuded with many tag teams on Smackdown until lising to their personal stylist Rico and Rikishi (a team that was put together by Mr. McMahon). They won the titles right back two weeks later and held them for a month before losing to the team of Edge and Hulk Hogan. Billy and Chuck were set to be storyline married but at the ceremony, they revealed that this was a storyline. This was the apex of the Billy and Chuck angle as they disbanded after Gunn took time off for a shoulder injury. Upon returning in 2003, he tagged with Jamie Noble and was only used on WWE Velocity for the rest of his time on the WWE until his release in November 2004.

In February 2005, he debuted in TNA Wrestling as The Outlaw to help Jeff Jarrett retain his NWA Heavyweight Championship. It took months but the newly named Kip James and B.G. James rejoined forces in TNA as The James Gang. After feuding with Konnan and his LAX group, they realy did notn have much to do and showed their displeasure toward TNA. After a hiatus, they returned renamed the Voodoo Kin Mafia (or VKM which is the initials of Vince McMahon). The team lasted until James turned on both B.G. and his father Bob Armstrong. James was repackaged at "The Mega-Star" Kip James but nothing came of it and later was put with The Beauftiful People stable. He stayed in TNA until his release in December 2009.