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Road Dogg
After defeating Barry Hardy in a dark match on the August 16, 1994 episode of WWF Wrestling Challenge, James signed with the World Wrestling Federation towards the end of 1994. He was billed as The Roadie, an assistant to "Double J" Jeff Jarrett, a would-be country singer. He wrestled on several pay-per-views and television shows, but most of his first WWF tenure was spent accompanying Jarrett and interfering in his matches. In early 1995, Jarrett released the song "With My Baby Tonight", which Jarrett claimed he had sung himself. The planned angle was to reveal that it was The Roadie, not Jarrett, who had really performed the vocals on this song, sparking a feud between the two wrestlers. Before this revelation could take place, James and Jarrett suddenly left the WWF following the second In Your House pay-per-view on July 23, 1995.

James, without Jarrett, returned to the WWF in 1996 under the ring name Jesse James, where he revealed himself as "The Real Double J" and the true singer of "With My Baby Tonight". He languished as a mid-card singles wrestler until beginning a feud with The Honky Tonk Man. After denying Honky Tonk Man's offer at becoming his manager by attacking him with his own guitar, James also began feuding with Honky Tonk Man's protégé Rockabilly. After trading wins against each other on television and pay-per-view, James, now referring to himself as "The Road Dogg" Jesse James (or simply Road Dogg) suggested to Rockabilly that that they form a tag team in order to end their unsuccessful runs as a singles competitors. A change in creative direction in the WWF in late 1997 led Rockabilly to accept James' offer after subsequently attacking Honky Tonk Man with his own guitar to cement their alliance. Soon after, Rockabilly reverted to his Billy Gunn ring name, dyed his hair back to its original blond color, and adopted the nickname "Badd Ass", while Road Dogg began to grow out and braid his hair. In addition to these aesthetic changes, their mannerisms became consistently more controversial and antisocial, with the team ultimately becoming known as the New Age Outlaws following their victory over the Road Warriors for their first Tag Team Championship. The Outlaws would continue to feud with the Road Warriors and later 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 Tag Team Championship reigns and managed to become singles champions while still together, with Road Dogg and Gunn each winning the Hardcore Championship once in 1998 and 1999, respectively, while Road Dogg would also go on to win the Intercontinental Championship in March 1999. The team came to an end when Gunn was legitimately injured in early 2000 and, to explain the absence needed for his recovery, Gunn was expelled from DX due to losing his temper. James then teamed with fellow DX member X-Pac throughout the summer of 2000, but failed to regain any championship success. The team eventually split, with Road Dogg and X-Pac subsequently feuding with each other before the entirety of DX fell apart. Road Dogg then formed a tag team with newcomer K-Kwik before being released from the company in January 2001 due to drug and personal problems.

On April 2, 2011, James returned to WWE for the first time in over a decade to induct his father "Bullet" Bob Armstrong into the company's Hall of Fame class of 2011.

On October 10, 2011, James announced on his Facebook account that he re-signed with WWE as an agent and producer and would return to the company in his new roles on October 23 at the Vengeance pay-per-view. After a ten-year long absence, James returned to WWE television on the December 12 episode of Raw under his Road Dogg ring name to present CM Punk with the Slammy Award for "Pipe Bomb" of the Year. On January 29, 2012, Road Dogg entered the Royal Rumble match as the twenty-third entrant and lasted nearly five minutes before being eliminated by Wade Barrett. Following this, James began hosting the WWE.com and YouTube web series Are You Serious? alongside Josh Mathews. On July 23, Road Dogg reunited with Billy Gunn, X-Pac, Triple H, and Shawn Michaels to reform D-Generation X for one night only on the 1000th episode of Raw.

On the December 17 episode of Raw, Road Dogg and Billy Gunn reformed the New Age Outlaws for one night only as they presented the Slammy Award for Comeback of the Year to Jerry Lawler. On the March 4 2013 episode of Raw, Road Dogg and Billy Gunn made their in in-ring return as the New Age Outlaws with a victory over Primo and Epico. On March 11, 2013, they accepted a challenge from Team Rhodes Scholars and faced them in a match, which was interrupted by Brock Lesnar, who hit both Outlaws with an F5. On the December 9 episode of Raw, the New Age Outlaws appeared to present the Slammy Award for LOL Moment of the Year.

On the January 6, 2014 episode of Raw, the New Age Outlaws saved CM Punk from an assault by The Shield and later stood in Punk's corner during his match against Roman Reigns. Later that week on SmackDown, they teamed alongside Punk to face The Shield in a six-man tag team match, although they were defeated after Gunn was pinned by Reigns. On the January 13 episode of Raw, the New Age Outlaws and Punk faced The Shield in a rematch before abandoning Punk as he was about to tag them, turning both Outlaws heel in the process for the first time in over a decade. Later that week on SmackDown, the New Age Outlaws defeated the Tag Team Champions Cody Rhodes and Goldust  in a non-title match. On January 26 at the Royal Rumble kickoff show, the New Age Outlaws defeated Rhodes and Goldust to win their first Tag Team Championship and sixth tag team title in WWE overall. They successfully defended the titles at Elimination Chamber against The Usos, but lost them to the twins on the March 3 Raw, ending their reign at 36 days. At Wrestlemania XXX the Outlaws and The Director of Operations Kane were quickly defeated by The Shield. The New Age Outlaws were then written off TV after receiving a Triple Powerbomb from The Shield after the match. On the January 19, 2015, episode of RAW, Road Dogg and Billy Gunn reunited to confront The Ascension. The Ascension had been disrespecting tag teams from the past when the New Age Outlaws music hit and they entered the ring wearing Dallas Cowboys shirts. The Outlaws, along with Bradshaw and Farooq of APA, cleared the ring of The Ascension. It was later announced that the New Age Outlaws will face The Ascension at the 2015 Royal Rumble.

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