On the April 11, 2016 episode of Raw, Anderson made his debut alongside Luke Gallows as heels, 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 on 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, 2019 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 show 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." Anderson participated in the Royal Rumble match at the namesake pay-per-view and entered at #20, but was eliminated by Randy Orton. At WrestleMania 36, Gallows and Anderson were involved in the Boneyard match between AJ Styles and The Undertaker, where Anderson was given a Tombstone Piledriver on the roof of a dilapidated building. On April 15, 2020, Anderson, along with Gallows and many other superstars, was released from his WWE contract.
On the October 10, 2022 episode of Raw, Gallows and Anderson made their unannounced return to WWE, aiding AJ Styles in attacking The Judgment Day. As part of the 2023 WWE Draft, Anderson was drafted to the SmackDown brand alongside Gallows 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.