Road Dogg made an appearance in WCW under the ring name Brian Armstrong on the November 30, 1991 episode of Saturday Night in a losing effort to Steve Austin.
Beginning in 1994, Armstrong wrestled more frequently for WCW, including a championship match against the World Television Champion Lord Steven Regal, which he lost. On the March 5, 1994 edition of the WCW Power Hour, Armstrong lost to Terra Ryzing in the latter's debut match for the promotion. Brian wrestled primarily on television tapings, and began to team frequently with his brother Brad, albeit in losing efforts.
On the November 14, 1994 edition of WCW Pro, Armstrong again lost to Terra Ryzing, who by that time had been repackaged as Jean-Paul Lévesque. He wrestled his final match for WCW on the December 17 episode of WorldWide, as he and his brothers Brad and Scott lost a six-man tag team match to The Three Faces of Fear (Kevin Sullivan, The Butcher, and Avalanche).
After defeating Barry Hardy in a dark match on the August 16, 1994 episode of WWF Wrestling Challenge, he 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, Roadie and Jarrett suddenly left the WWF following the second In Your House pay-per-view on July 23, 1995.
Roadie, 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 an undercard singles wrestler until beginning a feud with The Honky Tonk Man. After denying Honky Tonk Man's offer at becoming his manager by destroying his 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, suggested to Rockabilly that they form a tag team in order to end their unsuccessful runs as 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 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 Legion of Doom for their first Tag Team Championship. The Outlaws would continue to feud with the Legion of Doom 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 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, and competed in his last televised match on December 23. He was then indefinitely suspended, and later released from his contract in January 2001.
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. Several months later, James announced on October 11 that he re-signed with WWE as a producer, and would return to the company in his new role 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 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, he 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, Shawn Michaels and Triple H to reform D-Generation X for one night only on the 1000th episode of Raw. On the December 17 episode of Raw, he and Billy Gunn appeared together as the New Age Outlaws and 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-ring return as the New Age Outlaws with a victory over Primo and Epico. A week later, the New Age Outlaws competed against Team Rhodes Scholars, but the match was rendered a no contest after Brock Lesnar interrupted and performed an F-5 to both Outlaws as part of his ongoing feud with Triple H. 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 WWE 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 WWE Tag Team Championship and sixth tag team title in WWE overall. They held the title until the March 3 episode of Raw, where they were defeated by The Usos. After losing the title, the Outlaws allied with Kane as part of The Authority to face The Shield at WrestleMania XXX, but they were defeated.
Following WrestleMania XXX, James resumed his role as a producer while Gunn resumed his role as a trainer in NXT. On the January 19, 2015 episode of Raw, the New Age Outlaws returned alongside The Acolytes Protection Agency and the New World Order to confront and ultimately drive off The Ascension after they had been disrespecting tag teams from the past. Six days later, the Outlaws challenged The Ascension at the Royal Rumble, but were defeated. At WrestleMania 31, Road Dogg and the rest of D-Generation X (X-Pac and Billy Gunn) did a run in during Triple H's match against Sting which resulted in a brawl with the NWO (Hulk Hogan, Scott Hall and Kevin Nash) at ringside.
In January 2018, James made a one night return to Raw 25 Years, as part of the D-Generation X reunion. Later on at the show, they celebrated with the Balor Club, after attacking The Revival. James would later appear at the 2018 WWE Hall of Fame ceremony to induct Jeff Jarrett. On the January 28, 2019 episode of Raw, Road Dogg made a surprise appearance, where he joined Jeff Jarrett in interrupting Elias, and the two sang "With My Baby Tonight" until they were both attacked by Elias, with both Road Dogg and Jarrett being smashed with a guitar. On the February 4, 2019 edition of Raw, he was in Jarrett's corner for his first match in WWE for 19 years against Elias. After Elias won the match, he attacked him from behind to set up a guitar shot from Jarrett. On April 7, 2019, Dogg was inducted in the WWE Hall of Fame as part of D-Generation X.