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Steven Richards made his WWF debut on the August 15, 1999 episode of Sunday Night Heat, helping out his old tag team partner, The Blue Meanie. The two briefly became a tag team before Richards took on the gimmick of an impersonator. Mocking various then-current characters, he appeared as an Acolyte, a Dudley Boy, and a member of the Brood until briefly settling on Mick Foley's old Dude Love persona. Once he was done with the Dude Love character, Richards would go on to portray Test, Chyna, and Chris Jericho before suffering an ankle injury. He returned to a stint on WWF's tertiary shows (Jakk'ed and Metal), in which he largely found himself on the losing end of several matches.

Richards returned to the main roster on the June 26, 2000 episode of RAW, with an entirely new look and gimmick, cutting his hair short and wearing a suit and tie. In the weeks following, he cut promos condemning the risque content of WWF's programming and preaching conservative values. He became a full fledged villain forming a stable known as the Right to Censor, and becoming a manager and partner for his recruits, including The Godfather (renamed the Goodfather), Bull Buchanan, Ivory, and Val Venis. When Chyna was featured in Playboy magazine, Richards demanded a match between Chyna's associate Eddie Guerrero and Val Venis. After Chyna had pantsed Richards leaving him in his white socks and blue briefs, costing Venis the match, Richards and his stable feuded against her.

After the Right to Censor stable broke up, Richards found himself off programming for a short time. Not long afterward, he cut a promo condemning The Undertaker for brutally attacking the Right to Censor, causing the group to disband. When Undertaker confronted Richards, KroniK attacked him. He quickly confirmed his alliance with the tag team, thus becoming a de facto member of The Alliance and managed them briefly before they were quickly released. Richards remained on the brand's "B" shows until Team Alliance lost at Survivor Series in 2001. Richards was fired along with the rest of the alliance roster by Vince McMahon until Ric Flair was able to save his job and get him drafted over to the Raw brand. There, Steven Richards began using the gimmick of a psychotic jobber and became a twenty-two-time Hardcore Champion trading it several times with Bubba Ray Dudley, Booker T, Crash Holly, Shawn Stasiak, Justin Credible, Bradshaw, Terri, and Tommy Dreamer. Richards would team with Justin Credible to lose to The Big Show in a 2 On 1 Handicap Match on the Heat before Backlash in 2002.

Richards eventually formed an alliance with Victoria in late 2002 as a psychotic couple helping each other win their matches. Richards also helped Victoria retain her WWE Women's Championship. It was also around this time that Richards would first proclaim himself the General Manager of Heat. During a match on Heat with Heidenreich in November 2003, Richards almost broke his neck when Heidenreich botched an Electric chair maneuver, but Richards was not seriously injured and continued to compete on Heat and occasionally on Raw in late 2003-early 2004. As Victoria started to make her latest face turn, the duo quietly separated. In August 2004, Richards began dressing in drag as "The Mystery Woman" and helping Victoria win matches. He was finally unmasked at Unforgiven when saving Victoria from Tyson Tomko and then heel Trish Stratus, but ended up being squashed in an impromptu match to Tomko. Richards would then go on a long losing streak on Heat in late 2004 into early 2005.

Richards's role as a jobber has been at times physically tasking and he was legitimately injured during the Raw debut match of Chris Masters in February 2005, after a botched Polish hammer. After returning from injury, Richards faced Masters in a rematch but lost to Masters for a second time.

Richards made an appearance at the ECW reunion event ECW One Night Stand in 2005, reuniting with his bWo comrades and proclaiming "We have only three words for you. We're – taking – over!" Richards then went on to drop The Sandman with a Stevie Kick. Richards was traded to SmackDown! on June 30, 2005 and reprised the bWo group with Nova and The Blue Meanie. At the Great American Bash, the bWo lost to The Mexicools (Juventud Guerrera, Psicosis, and Super Crazy) in a six-man tag team match. Richards went on to become the main eventer of WWE Velocity (much like his time on Heat) and began slowly dropping the bWo gimmick as he jobbed to the likes of Hardcore Holly, Vito, and Booker T. After a while, Richards would not be used on SmackDown! or even Velocity as he seemingly disappeared for over half a year. Richards made his return to the ring during an 18-Man pre-show Battle Royal before WrestleMania 22.

Shortly after the introduction of the ECW brand in 2006, Richards left the SmackDown! brand to join the ECW brand, starting with the WWE versus ECW Head to Head show on June 7, 2006. Richards went on to appear on ECW's weekly show under his old ring name of Stevie Richards. Richards soon returned to his heel persona, jobbing the other ECW Originals and siding with the newer stars. He picked up his first win on ECW's weekly show on September 5, 2006, against Balls Mahoney, after interference from Kevin Thorn, who was feuding with Mahoney at the time.

Richards was part of the new ECW brand's first pay-per-view, December to Dismember, defeating Rene Dupree in a pre-show dark match. Other than this contest Richards did not appear on ECW between September 2006 (when he joined up with the first version of ECW's New Breed - Test, Mike Knox and Hardcore Holly) and February 2007 (when he lost to CM Punk for a second time). Richards appeared as a Lumberjack in the pre-WrestleMania 23 Lumberjack Tag Team match. He would then go on to lose to CM Punk a further three times. In mid-2007, Richards turned face again due to fan reaction, and teamed with Tommy Dreamer against the New Breed on house shows, replacing The Sandman (who was drafted to Raw) in the ECW Originals.

Richards returned to SmackDown in November 2007. He only competed in two matches before being released again. On July 24, 2008 Richards defeated Thorn in an upset after reversing a crucifix bowerbomb into a backslide pin. This was Richards' first victory on WWE television since September 2006. A week later a re-match took place throughout which Richards was dominated, however he defeated Thorn once again via roll-up. On August 7, he was ambushed by Thorn while giving an interview backstage. He would once again defeat Thorn on August 14 by disqualification after the referee declared a disqualification when Thorn continued to massively "destroy" Richards after Thorn had already won. He would then get revenge by ambushing Thorn while giving an interview the next week. Their feud would continue with Richards teaming up with Dreamer and CM Punk on different occasions against Thorn and Elijah Burke with Richards losing and winning a match. Richards was eliminated from the Elimination Chase for the ECW Championship on the September 18 edition of ECW. He was then absent from WWE programming due to having throat surgery.

Almost five months later, Richards made his return on the February 12, 2008 edition of ECW, defeating a jobber with his signature Stevie-T. He would then go on to beat another jobber, followed by a victory over Mike Knox (this was Richards last victory on WWE Television). In the following months Richards would compete in the pre-WrestleMania 24-Man Battle Royal, lose to Shelton Benjamin and The Great Khali, team with Kelly Kelly to lose to Mike Knox and Layla, lose to Mike Knox in a singles match and appeared as one of the fourteen ECW Superstars who faced Triple H and Mr. Kennedy in a 14 On 2 Handicap Match on Raw. Richards would commentate on the Extreme Rules match between Mike Knox and Tommy Dreamer on the 100th episode of ECW. He would remain with ECW in the June 2008 Draft, however would wrestle his last three matches with the company on SmackDown!. He lost to Vladimir Kozlov twice in July 2008. He wrestled what turned out to be his last match in the company, as he lost to The Brian Kendrick and was released from his WWE contract shortly thereafter on August 15, 2008.

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