The Outlaws first formed on the October 4, 1997 episode of WWF's Shotgun Saturday Night, when struggling superstars Billy Gunn and "Road Dogg" Jesse James, then known as Rockabilly and "The Real Double J" Jesse James respectively, ended their feud and teamed up.
On a later edition of Shotgun, Jesse James walked out to the ring following a loss by Rockabilly and asked him to turn on his manager The Honky Tonk Man and team with him. Rockabilly answered by smashing a guitar on Honky Tonk Man's head and telling James he was in. Rockabilly re-dubbed himself "Badd Ass" Billy Gunn and Jesse James rechristened himself the Road Dogg. The team made an immediate impact on the WWF tag team scene with blatant attacks against other tag teams and, initially not having an entrance theme, walking out to the ring with only Road Dogg making a rant against their opponents over the PA system. The team became known for pulling wins out of nowhere via cheating and use of weapons.
James and Gunn defeated the Legion of Doom for the WWF Tag Team Championship in November 1997. This marked Gunn's fourth Tag Team Title reign and Road Dogg's first. Not only did the team win the titles that night, but they also got their "Outlaws" nickname when they "stole" the win and then ran to a waiting car, prompting Raw announcer Jim Ross to liken them to outlaws leaving a robbery. The name stuck and the New Age Outlaws quickly became one of the most hated teams in the WWF. During their feud with LOD, the Outlaws joined Triple H and Shawn Michaels, collectively known as D-Generation X, in assaulting the team on an episode of Monday Night Raw, including shaving off one of Road Warrior Hawk's mohawks and throwing Road Warrior Animal through the announcers' table.
Shortly before the Royal Rumble in 1998, the New Age Outlaws began a feud with Mick Foley, first fighting him as Dude Love, then as Mankind and finally Cactus Jack. When it became apparent that he needed help dealing with the Outlaws, Foley brought in Terry Funk as Chainsaw Charlie. Following a disqualification against The Legion of Doom at the Royal Rumble, the team were confronted by DX, who told them they needed to start making waves by acting more controversially. In response to this, the Outlaws locked Cactus Jack and Chainsaw Charlie in a dumpster and threw it off the entrance ramp on to the concrete floor. The Outlaws initially looked concerned, but ultimately attacked their injured rivals in what Foley would describe as "one of the funnier examples of bad sportsmanship". At WrestleMania XIV, the New Age Outlaws lost the titles to Cactus Jack and Chainsaw Charlie in a dumpster match. The next night on Raw, however, with the aid of Triple H and X-Pac, the Outlaws regained the titles in a steel cage match and officially joined DX.
The growing popularity of the "new" DX quickly turned the group from heels to tweeners, eventually becoming faces, and they feuded with many different tag teams over the course of 1998. They lost the tag titles to Kane and Mankind in the summer of 1998, only to regain the titles from that same team at SummerSlam in a handicap match after Kane no-showed. In late 1998, Vince McMahon's Corporation tried to tempt the Outlaws away from DX and failed, which led to the Outlaws losing the titles to Corporation members Ken Shamrock and Big Boss Man.
As 1999 started, the Outlaws slowly began to drift apart, with each man striving for singles gold. Road Dogg held both the Hardcore Title and the Intercontinental Championship in the first few months of 1999 (including a successful Intercontinental Title defense at WrestleMania XV), and Gunn briefly held the Hardcore title as well. In March, the pair started to team once again, leading to a match with Jeff Jarrett and Owen Hart at Backlash in April. A week later, Gunn turned heel on Road Dogg, resulting in a feud and a match at Over the Edge. The following month, Gunn went on to win the King of the Ring tournament.
During the fall of 1999, the Outlaws reunited, first as faces, but then as heels when they rejoined the reformed and now-heel DX. No Way Out 2000 saw the final end of the Outlaws when Gunn received a serious arm injury during a match with the Dudley Boyz. Gunn was soon kicked out of DX after "losing his cool" and getting into a fight with all of the DX members. Road Dogg was released from his WWF contract in early 2001 while Gunn was released from his contract in 2004 after eleven years with the company.
On July 23, 2012, the New Age Outlaws returned to WWE on the 1000th episode of Raw to re-unite with X-Pac, Shawn Michaels and Triple H to reform D-Generation X for one night only. On December 17, Billy Gunn and Road Dogg appeared to present the Slammy Award to Jerry Lawler for Comeback of the Year. On December 26, the team reunited to face Team Rhodes Scholars in a house show loop.
On the March 4, 2013 episode of Old School Raw, the New Age Outlaws competed in their first televised tag team match in WWE since February 2000, where they defeated Primo and Epico. The following week on Raw, the New Age Outlaws answered a challenge to take on Rhodes Scholars, but during the match they were attacked by Brock Lesnar, who was in a feud with Triple H at the time.
On the January 6, 2014, episode of Old School Raw, the Outlaws were in the corner of CM Punk during his match against Roman Reigns. On the January 10 episode of SmackDown, the Outlaws teamed with CM Punk in a six-man tag match against The Shield in a losing effort. On the January 13 episode of Raw, the Outlaws again teamed with Punk in a rematch against The Shield, only to abandon Punk and lose the match, thus turning heel in the process for the first time since 1999. Four days later on SmackDown, they defeated WWE Tag Team Champions Cody Rhodes and Goldust in a non-title match. At the Royal Rumble, the Outlaws defeated Rhodes and Goldust to become WWE Tag Team Champions, their first reign with these particular title, their sixth overall tag team championship reign in WWE and first in over fourteen years, marking the longest time between reigns in WWE history. The following night on Raw, Rhodes and Goldust invoked their rematch clause, with the Outlaws retaining the title after losing by disqualification after Brock Lesnar interfered and attacked both Rhodes and Goldust. On the February 3 episode of Raw, Triple H granted Rhodes and Goldust a rematch for the titles in a steel cage match, in which the Outlaws would retain their titles. At Elimination Chamber, the Outlaws successfully defended their titles against The Usos, but lost the championships in a rematch to The Usos on the March 3 episode of Raw. The New Age Outlaws, now billed as "The Corporate Outlaws", teamed with Kane to take on The Shield in a losing effort at WrestleMania XXX. Billy Gunn got injured on the night by a Triple Power Bomb that The Shield delivered to him, causing The New Age Outlaws to not appear on Raw and the following night on SmackDown.
On January 19, 2015 on Raw, they, along with the APA and nWo, returned as faces and attacked The Ascension. This set up a match between the Outlaws and The Ascension at the Royal Rumble. They went on to lose to The Ascension after a Fall of Man on Gunn. At WrestleMania 31, The Outlaws, along with X-Pac and Shawn Michaels, assisted their DX partner Triple H in defeating Sting and also fought against the nWo, who had come to aid Sting.
On January 22, 2018 on the 25th anniversary of Raw, The New Age Outlaws appeared together with DX and Scott Hall. During the segment, the historic stable established an alliance for one night only, with the Bálor Club. Later that evening, the Bálor Club defeated the Revival, and after the match the legends of the past performed on the latter, their classic finishers and signature taunts, with a Shake, Rattle and Roll from Road Dogg and a Famouser from Billy Gunn against Scott Dawson.