Simmons joined the World Wrestling Federation (WWF) and made his debut on the July 22, 1996, episode of Raw. His first gimmick was that of Faarooq Asad, a gladiator who wore a black and blue gladiator outfit with a misshaped helmet and was managed by Sunny. Simmons started his first feud with Ahmed Johnson before shortening his ring name to Faarooq.
As Faarooq, Simmons dropped his gladiator gimmick and with his new manager, Clarence Mason, formed a stable known as the Nation of Domination. They mostly feuded with Ahmed Johnson, who Faarooq was combating before. Faarooq's ongoing "war" with Johnson included matches at the Royal Rumble in 1997, where Ahmed won by disqualification, and another at WrestleMania 13 where Ahmed recruited the Legion of Doom to take on the entire Nation in a Chicago Street Fight, which was won by Johnson and the Road Warriors. The group stayed together until Faarooq became angry with them for costing him the WWF Championship. After Simmons threw Crush and Savio Vega out of the Nation, Crush and Vega formed their own rival factions, known respectively as the Disciples of Apocalypse and Los Boricuas, and Faarooq recruited more African American members for the Nation. The three stables feuded with one another throughout 1997. In early 1998, Simmons's leadership of the Nation of Domination was usurped by The Rock, and he spent several months feuding with his former stablemates.
After being dumped from the Nation, Simmons teamed briefly with 2 Cold Scorpio. In late 1998, Simmons began teaming with Bradshaw as Hell's Henchmen. They were managed by The Jackyl until he left the WWF, at which point they were repackaged as members of The Undertaker's Ministry of Darkness and were renamed the "Acolytes", as they acted like acolytes to The Undertaker. The Acolytes recruited Phineas I. Godwinn and Mabel to the Ministry by kidnapping and brainwashing them (renaming them Mideon and Viscera, respectively), and feuded with The Undertaker's rivals, such as D-Generation X and The Brood, the latter of which later joined the Ministry of Darkness as well.
After The Undertaker suffered an injury in late 1999, the Ministry of Darkness disbanded. Simmons and Bradshaw continued to team with one another, and eventually adopted the gimmick of two brawlers who enjoyed drinking beer and smoking cigars, becoming faces in the process. After Bradshaw began hiring out the services of the Acolytes as mercenaries and bodyguards, the tag team was renamed the Acolytes Protection Agency (APA).
The APA teamed together until 2002, when Simmons was drafted to the SmackDown! brand. Around this time, Simmons changed his ring name to his real name. Simmons had a brief heel run when he teamed with Reverend D-Von until he left television in December 2002, but in June 2003 he returned to WWE with Bradshaw and the APA reunited.
In his last WWE storyline, he was fired by former SmackDown! General Manager Paul Heyman . It was assumed the APA would be fired, but it turned out to only be Faarooq. Simmons retired from his in-ring career, kayfabe accusing Bradshaw of not being a faithful friend.
Starting on October 23, 2006, he began making short cameos on Raw under his given name. On the November 20, 2006, edition of Raw, Simmons was chosen by Ric Flair to replace the injured Roddy Piper at the Survivor Series to take on the Spirit Squad. He was the first to be eliminated, via countout. He was seen in the ring with Chris Masters in the "Master Lock Challenge" on the January 15, 2007 edition of Raw, a confrontation which ended prematurely after interference from Super Crazy. Although Simmons technically broke the Master Lock, it was not officially recognized because of Crazy's interference. On the July 27, 2007, edition of SmackDown!, Simmons was named the best man for Theodore Long and Kristal's wedding.
Simmons also engaged in a feud against Santino Marella. On September 10, 2007, on Raw, Simmons was attacked by Marella. On the September 24, 2007, edition of Raw, Simmons made a return to the ring and defeated Santino Marella by countout after Marella left the ring and walked out.
Simmons occasionally competed on WWE Heat, taking on jobbers from the town in which the show is being taped. On December 3, 2007, Simmons and Bradshaw were hired by Hornswoggle to help him in a no disqualification handicap match against Jonathan Coachman and Carlito in which they helped him win. Simmons appeared on Raw's 800th episode on November 3, 2008. He also returned during the 2008 Slammy Awards with Mickie James to give The Great Khali the D@!n Moment of that year's Slammy Awards.
Simmons was released from WWE on January 13, 2009, due to budget cuts. Simmons showed up backstage on the November 15, 2010 episode of WWE Old School Raw. Simmons appeared once again on the May 2, 2011, episode of Raw in a backstage segment for The Rock's birthday celebration.
In 2012, it was announced that Simmons would be inducted into the WWE Hall of Fame. He was formally inducted on March 31 by his APA partner John "Bradshaw" Layfield.
Simmons and Layfield reunited as the Acolytes Protection Agency (APA) on the 1000th episode of Raw, providing their signature protection and back-up for Lita during her match with Heath Slater. Simmons appeared again during the Hell in a Cell Pay per view during the segment with Theodore Long, Eve, Zack Ryder and Santino Marella. Simmons appeared again on the Slammy awards on Monday Night Raw with Kane, Daniel Bryan and Ric Flair as they were saying "yes", "woo" and "no" respectively. Simmons showed up on the January 28th 2013 episode of RAW watching a dance off between Brodus Clay and Tensai. Simmons showed up again almost a year later on the January 6, 2014 Old School Raw in a backstage segment with DDP and Booker T.