On May 29, 2006, Gallows debuted on Raw as an imposter Kane. Wearing Kane's old mask and ring attire, he chokeslammed Kane during his match against Shelton Benjamin for the WWE Intercontinental Championship. Subsequently, the imposter Kane repeatedly attacked the real Kane during or after his matches. The pair finally faced off in a match at the Vengeance pay-per-view, with Gallows winning using one of Kane's trademark moves. One night later, however, the storyline was abruptly ended when the original Kane attacked the Imposter Kane, removed his mask, and threw him out of the building.
Gallows was then renamed Festus and was partnered up with fellow wrestler Jesse, and on the June 29, 2007, episode of SmackDown!, vignettes hyping Jesse and Festus began to air. For weeks, Jesse was presented as the mouth-piece of the tandem, who was in awe of his tag team partner. Festus, however, played a character that was mentally challenged and unresponsive. In spite of Festus' dimwitted nature, Jesse kept claiming that Festus was an emotionally driven and physically unstoppable giant. On the September 7, 2007, episode of SmackDown!, there was a segment featuring Jesse and Festus now actually in the arena rather than in a studio. On October 5, Festus won his debut match on SmackDown! with Jesse. When the opening bell rang, Festus' personality changed into a very focused and angry competitor as compared to the mentally challenged character he had portrayed. When the bell rang to signify the end of the match, Festus returned to his docile self. On the December 21 episode of SmackDown!, Festus defeated Deuce in a Santa Match, with both of them wearing Santa Claus outfits. On the January 25 episode of SmackDown!, Jesse explained the reason that they had not been on television was because Festus has been seeing doctors about his "problems".
In 2008, before the bell rang, Jesse explained that Festus had changed. However, Festus did not change and continued to make a determined and monstrous face after the bell had rung. On the March 21 episode of SmackDown, Jesse and Festus had a chance to face John Morrison and The Miz for the WWE Tag Team Championship, but Morrison and The Miz retained the title. Festus received his first loss when he wrestled against World Heavyweight Champion The Undertaker on the April 11 episode of SmackDown!, after passing out while in the Hell's Gate.
On April 15, 2009, Festus was drafted to the Raw brand as part of the 2009 Supplemental Draft and, as a result, was separated from his tag team partner Jesse, who remained on SmackDown.
After a three-month hiatus from television, Festus returned on the November 27, 2009, episode of SmackDown!, repackaged as a villain under the name Luke Gallows, sporting a new attire with a goatee and shaved head. After accompanying CM Punk to the ring for his match with Matt Hardy, Punk revealed that Gallows was actually Festus' true identity and claimed that Gallows' family and friends enabled his alcoholic inclination, which led to the mental state he was in as Festus, before stating that Gallows was cured due to Punk showing him the straight edge lifestyle. On the December 11 episode of SmackDown!, Gallows and Punk defeated Hardy and R-Truth, after Gallows pinned Hardy with his new finishing move, the "Twelfth Step". On the January 8, 2010, episode of SmackDown, Gallows defeated Hardy. The next week, Gallows and Punk defeated Matt Hardy and The Great Khali, The Hart Dynasty, and Cryme Tyme in a fatal four-way match to become the number one contenders for the Unified WWE Tag Team Championship.
On the February 10 episode of Raw, The Straight Edge Society was eliminated in a Triple Threat elimination tag team match between them, The Miz and Big Show and DX for the Unified Tag Team Championship. The Miz and The Big Show became the new Unified Tag Team Champions. At WrestleMania XXVI Luke Gallows competed in a dark 30-man battle royal, which was won by Yoshi Tatsu. On the April 13 episode of NXT, he challenged CM Punk's rookie Darren Young and the stipulation, if Young lost, he would have to surrender his hair to Punk and have it shaved bald. Gallows came close to getting the victory when Young came up with a roll-up and saved his hair, with Punk showing some favor to his rookie and Gallows seeming unhappy. At Extreme Rules, during Punk's Hair match against Rey Mysterio, Gallows and Serena helped Punk throughout the match until they were banned from ringside.
On the July 2 tapings of SmackDown, after a match between Luke Gallows and Kane, a security video was shown by Serena of her being caught drinking in a bar by Punk on the same day of The Undertaker's attack proving The Straight Edge Society's innocence in order to save Punk. Serena begged for forgiveness even after Punk warned her not to, but the Straight Edge Society simply left without her. The following week, however, Serena was forgiven by Punk for her actions, as they embraced, but Gallows did not approve. The following week Gallows was set to fight Big Show but gave the match to the SES Masked Man, who was unmasked as Joey Mercury during the match. On the September 3 episode of SmackDown, Gallows and Punk faced The Big Show in a two-on-one handicap match, which Gallows and Punk lost. After the match Punk delivered the GTS on Gallows.
On the September 16 episode of WWE Superstars, before a match with MVP, Gallows cut a promo announcing that he was no longer part of the Society by proclaiming he was his own man. Gallows went on to lose the match. On the September 21 taping of SmackDown, Gallows began a slow face turn when he confronted CM Punk in a backstage segment stating that after defeating him, he would have a beer, but lost a match to Punk later in the night.
Gallows, now officially established as a face, defeated Vance Archer on the November 4 airing of Superstars. His final TV appearance was during a backstage segment in which Kane was looking for his father, on the November 19, episode of SmackDown. Gallows was released from his WWE contract on the same day, along with several other superstars.
On the April 11, 2016, episode of Raw, Gallows made his return to WWE alongside fellow wrestler Karl Anderson, attacking The Usos after their victory over The Social Outcasts, before being removed by several referees. On the April 18 episode of Raw, Gallows and Anderson attacked WWE World Heavyweight Champion Roman Reigns, following Reigns' promo with AJ Styles. The following week on Raw, Gallows and Anderson made their in-ring debuts, defeating The Usos. During this time, Gallows and Anderson helped Styles in his feud with Reigns, with Styles at first reluctant for their help. On the May 2 episode of Raw, Gallows and Anderson teamed with Styles, where they began being known as The Club, defeating Reigns and Usos. On the May 9 episode of Raw, The Club faced Reigns and Usos in a Six-man Elimination match, where, following the elimination of both Gallows and Anderson, Reigns and Usos won by disqualification after Gallows and Anderson attacked Reigns with a steel chair. At Extreme Rules, Gallows and Anderson interfered in Extreme Rules match for WWE World Heavyweight Championship. They attacked Reigns until The Usos, who lost their Tornado Tag Team match to Anderson and Gallows earlier in the night, brawled with the two until Reigns would retain. The following night on Raw, Styles requested to leave The Club. Gallows and Anderson left Styles shortly after Styles lost to Kevin Owens in a Money in the Bank qualifying match. On the May 30 episode of Raw, Styles would confront a returning John Cena who said the "new era" would have to go through him, before offering Styles his hand. Styles shook his hand, shortly before Gallows and Anderson interrupted. As Styles and Cena appeared ready to fight Gallows and Anderson, Styles instead beat down Cena repeatedly, reuniting The Club.
On July 19, as part of WWE draft, both Gallows and Karl Anderson were drafted to Raw, while AJ Styles was drafted to SmackDown, splitting up The Club. Gallows and Anderson resumed feuding with The New Day, and took out Big E with a groin injury after a sneak attack. Following this assault, Gallows and Anderson made fun of the situation by appearing in segments dressed as doctors and claiming to be in need of a cure for "Ringpostitis", leading up to a SummerSlam match for the WWE Tag Team Championship, which they won by disqualification because of show guest Jon Stewart and a returning Big E getting involved. At Clash of Champions, Gallows and Anderson failed to win the titles. On the November 7 episode of Raw, Gallows and Anderson were announced as part of Team Raw for the 10–on–10 Survivor Series Tag Team Elimination match at Survivor Series. The same night, while being at odds with the rest of Team Raw, they defeated The New Day in a non-title bout.
On the January 18, 2017 episode of Raw, Gallows and Anderson appeared to defeat Cesaro and Sheamus by pinfall for the Raw Tag Team Championship; however, due to Sheamus having hit the referee, the decision was reversed to a disqualification, leading to them winning the match but not the title. On the Royal Rumble pre-show, Gallows and Anderson defeated Cesaro and Sheamus to win the Raw Tag Team Championship for the first time. They lost the title to returning The Hardy Boyz at WrestleMania 33 in a fatal four-way tag team ladder match.
On the January 1, 2018 Raw, the duo turned face by appearing as Finn Bálor's surprise tag team partners. After a brief feud, they lost to The Revival at the Royal Rumble pre-show. On April 17, Gallows and Anderson were both drafted to SmackDown as part of Superstar Shake-up. On the May 22 episode of SmackDown, Gallows and Anderson defeated The Usos to become number one contenders for the SmackDown Tag Team Championship but they failed to win the title from The Bludgeon Brothers on the Money in the Bank pre-show and also lost a rematch on the June 19 episode of SmackDown.
On the April 29 episode of Raw, Gallows and Anderson returned to the Raw brand, losing to The Usos. On the July 1 episode of Raw, Gallows and Anderson encouraged AJ Styles to develop more of an edge. After Styles lost a United States Championship match to Ricochet; Gallows and Anderson helped Styles to beat up Ricochet, and reuniting The Club as heels. On the July 22 episode of Raw, The Club was renamed The O.C., as in the "Original Club". On the 30th July edition of Raw, Gallows and Anderson became two-time Raw Tag Team Champions by defeating The Revival and The Usos in a triple threat tag team match. On the August 19 Raw, they dropped the titles to Seth Rollins and Braun Strowman. At Crown Jewel, Anderson and Gallows won the WWE Tag Team World Cup, by defeating eight other teams, thus becoming the "Best Tag Team in the World." Gallows participated in the Royal Rumble match at the namesake pay-per-view and entered at #24 but was eliminated by Edge. At WrestleMania 36, Gallows and Anderson were part of the Boneyard match between AJ Styles and The Undertaker, with Gallows being thrown off of a building by Undertaker. On April 15, 2020, Gallows and Anderson were released from their WWE contracts, along with multiple other superstars.
On the October 10, 2022 episode of Raw, Gallows and Anderson made their unannounced return to WWE, saving AJ Styles from an attack by The Judgment Day after Styles fooled Finn Bálor into thinking he had joined them by embracing in a hug. The O.C. then challenged the Judgment Day to a match at Crown Jewel on November 5. where they lost due to interference from Rhea Ripley. Due to the interference, Mia Yim would join The O.C. to help fend off Ripley. As part of the 2023 WWE Draft, Gallows was drafted to the SmackDown brand alongside Anderson, Yim, and Styles. On the February 20, 2024 episode of NXT, Anderson and Gallows attacked Axiom and Nathan Frazer, and Chase University (Andre Chase and Duke Hudson) after the two teams faced each other. Gallows and Anderson wrestled their return NXT match on the March 25 episode of NXT, defeating Edris Enofe and Malik Blade.