James returned to the WWF in 1996 as Jesse Jammes, "The Real Double J", and revealed himself to be the true singer of "With My Baby Tonight". He languished as a midcard singles wrestler until he formed a tag team with Billy Gunn, New Age Outlaws. A change in creative direction in the WWF in late 1997 led Billy Gunn, who had formerly been stuck in the unpopular gimmick of "Rockabilly," to bleach his hair blonde and assume the name "Badd Ass" Billy Gunn (also known as Mr. Ass), while James became "The Road Dogg" Jesse James. The appearance and mannerisms of the team became more and more controversial and anti-social. The team, known as the New Age Outlaws, feuded with the Road Warriors and the short-lived tag team of Cactus Jack and Chainsaw Charlie before joining D-Generation X the night after WrestleMania XIV.
The Outlaws amassed five World Tag Team Title reigns before Gunn was (legitimately) injured in early 2000 and thrown out of DX to explain his absence. James then teamed with fellow DX member X-Pac throughout the summer of 2000 but failed to regain his former popularity or title success. The team eventually split, and DX fell apart. James then formed a tag team with newcomer K-Kwik. He was suspended in December 2000, and the WWF announced his release on January 26, 2001.
His most prominent appearance in the independent circuit was with the short lived World Wrestling All-Stars (WWA) promotion.
James debuted for the upstart Total Nonstop Action Wrestling (TNA) promotion on September 18, 2002 wrestling as B.G. James (the popular Road Dogg gimmick was owned by WWE). He was initially a heel and one of the founding members of Vince Russo's S.E.X faction.
In July 2003, James formed the stable known as the 3Live Kru with Hispanic wrestler Konnan and the African American wrestler Ron Killings (alias his old WWF ally K-Kwik). James was presented as a white trash redneck. The group was popular from the outset and was notable because they sang their own entrance music as they approached the ring. The 3Live Kru turned out to be a successful gimmick as Killings held the NWA World Heavyweight Championship for a second time and all three members enjoyed Tag Title reigns.
Tension arose when James' former partner Billy Gunn joined TNA as "The New Age Outlaw" (later shortened to "The Outlaw") in February 2005. The Outlaw repeatedly courted James, seeking to split the Kru and recreate the New Age Outlaws. When The Outlaw began feuding with the Kru, James repeatedly found his loyalties divided, unwilling to fight either his former or current tag team partners. For a time, James stopped appearing with the Kru but did not align himself with The Outlaw, who had by then changed his name to "Kip James" as a "tribute" to James' father. However, at Sacrifice 2005, he reasserted his allegiance with 3LK as special guest referee in a match between the other members of 3LK and the team of Kip James and Monty Brown.
Kip James tried to warm up to 3LK again in the lead-up to Bound for Glory by saving B.G. several times from Team Canada. At Bound for Glory, he offered his protective services to them against Team Canada (to neutralize Scott D'Amore, as he said). When they lost, Kip James came down to the ring, appearing ready to hit Konnan with a steel chair since he originally vetoed Kip's offer. Kip instead saved Konnan from Team Canada, thus proving his original intentions.
On the November 26 episode of Impact!, B.G. brought Kip and the 3LK to the ring and asked The Truth and Konnan to give Kip James a yes/no vote to be accepted into the group. After B.G. got heated with Konnan, both gave Kip yes votes and the 4Live Kru was born. The 4Live Kru would be short lived as Konnan, still apparently upset at Kip James's induction into the Kru, bashed both B.G. and Kip over the head with a steel chair at Turning Point 2005. Konnan, still wanting Ron Killings to be his "family," tried talking with The Truth. Killings told Konnan that he was done with the Kru and wanted to leave it all behind him.
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