Simmons joined the World Wrestling Federation and made his WWF debut on the July 22, 1996 episode of Raw. His first gimmick was that of 'Faarooq Asaad', a gladiator who wore a black and blue gladiator outfit with a misshaped helmet and was managed by Sunny. Simmons briefly feuded with Ahmed Johnson before changing his ring name to simply 'Faarooq'.

As Faarooq, Simmons dropped his gladiator gimmick and with his new manager, Clarence Mason, formed a stable known as the Nation of Domination. The Nation of Domination was loosely based on the Nation of Islam and the Black Panther Party, although the members of the stable were not exclusively African American. They mostly feuded with Ahmed Johnson, who Faarooq was combating with before. The group stayed together until Faarooq became angry with them for costing him the World title. So after Simmons threw the White American Crush and the Puerto Rican 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 then 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 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 (much like The Crusher and Dick the Bruiser before them) 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). Around this time, Simmons would start saying his trademark "DAMN!" catchphrase, though it wouldn't be emphasized as much as it would be later on.

The APA teamed together until 2002, when Simmons was drafted to the SmackDown! brand of World Wrestling Entertainment. Simmons had a brief heel run under his real name when he teamed with Reverend D-Von until he retired in December 2002, but in June 2003 he returned to WWE with Bradshaw and the APA reunited. One memorable moment during this short return was a joke shared by the two during which they claimed that the Basham Brothers' then-valet Shaniqua was actually Shelton Benjamin in drag.

In his last WWE storyline, he was fired by former SmackDown! General Manager Paul Heyman after he disrespected Heyman (due to the WrestleMania XX issue between Heyman and Stone Cold Steve Austin during that night). It was assumed the APA would be fired, but it turned out to only be Faarooq. Ron retired from his in-ring career, kayfabe accusing Bradshaw of not being a faithful friend. Simmons had decided to retire quietly in this manner due to injury and age. During that event, Heyman told Bradshaw that it was time for him to break out on his own again. Bradshaw went on to win the WWE Championship.

In 2006, during a rebroadcast of the 1981 Orange Bowl on Sun Sports, Ron stated that since that time he has retired from wrestling action, but would like to continue or even improve his role with World Wrestling Entertainment (WWE). Starting on October 23, 2006, he began making short cameos on Raw under his given name to say his catchphrase of "Damn!", often in awe of or shock at odd happenings. 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 Masterlock Challenge on the January 15, 2007 edition of Raw, a confrontation which ended prematurely after interference from Super Crazy. Although Simmons technically broke the masterlock, 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 kayfabe wedding.

Simmons also engaged in a feud against Santino Marella. On Monday, September 10, 2007 on Raw, Simmons was attacked by Marella. This was the first time that Simmons has been attacked by someone on screen for years. 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. A week later, Simmons said "Damn!" one more time after throwing Steve-O (of Jackass fame) out of a nearby door. After the showing of the event, a short segment was aired, promoting Steve-O's new show, which was premiering after Raw. The segment shown himself and Simmons once again, this time Simmons saying, "Then don't you have somewhere to be?" after Steve-O telling him about his show airing after Raw. This indicated the first time since his return to say a full sentence and not to say "Damn", and/or any word rhyming with it.

Ron Simmons occasionally competed on WWE Heat, taking on unknown wrestlers from the town in which the show is being taped. At the end of each match Ron Simmons holds onto a microphone, pulling it toward and away from his mouth while the crowd cheers then eventually will say "Damn!". On December 3, 2007 he 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 appearing on the entrance ramp and saying his signature phrase 'Damn!' while many superstars were dancing in the ring. He also returned during the Slammy Awards 2008 with Mickie James to give The Great Khali the DAMN Moment of the year Slammy Award.

Simmons was released from WWE on January 13, 2009 due to budget cuts.

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