Dean's first taste of superstar exposure came between 1992 and 1994 when WWF Chairman Vince McMahon used talent from various promotions as jobbers to various up and coming superstars on WWF programming.
In 2004, he was called up to start competing in SmackDown! dark matches and on Velocity. In his debut for World Wrestling Entertainment (WWE), Dean portrayed the gimmick of a physical-fitness guru. Introductory promos showed him "selling" his "Simon System", a supposed program of diet, exercise, and supplementation. The promos parodied fitness infomercials, as Simon routinely insulted his supposed customers.
During this gimmick, he acted as the sponsor of Raw, occasionally wrestling after first insulting the fitness of the crowd and the area in which they were located. After making only a minor impact on Raw, he formed a tag team with Maven who supposedly was a user of the "Simon System". With still only a minor impact made, Dean was traded to the SmackDown brand on June 30, 2005.
During a WWE produced ECW pay-per-view, One Night Stand, Dean appeared as Hollywood Nova with Da Blue Guy and Big Stevie Cool as the bWo.
When Dean moved to SmackDown! as part of the draft lottery, he joined the other members of the bWo and appeared as "Hollywood" Nova for his first appearance on the show. His next appearance for the brand was wrestling on its sister show, Velocity, as Simon Dean. The general belief was that the bWo appearance was going to be a one off, meaning Dean would keep to his "health sponsor" gimmick. It was announced, however, that the bWo would participate in a 6-man tag match at The Great American Bash against The Mexicools (Juventud, Psicosis, and Super Crazy). The announcement of this match occurred on the same edition of SmackDown! that his Simon Dean character had a match with Booker T. At the Great American Bash, the bWo lost to the Mexicools in the six-man tag team match. The appearance of the bWo soon faded as The Blue Meanie wasn't staying with the company and Richards began returning to his previous heel gimmick while Dean continued with the Simon Dean persona.
In late August, the Simon Dean character began coming to the ring on the Dean Machine (a Segway type machine). He would also force feed "Simon System" products to jobbers who wouldn't accept his offer to try them after defeating them in squash matches. The Simon Dean character had his first major WWE pay-per-view appearance at No Mercy, in a loss against Bobby Lashley. After the match, Lashley forced Dean to eat 20 double cheeseburgers, causing him to vomit backstage. Dean had been noted on his later appearances as the "Head of SmackDown!'s welcoming committee", a position in which he was used as a jobber to debuting wrestlers.
During the January 6, 2006 episode of SmackDown!, Dean came to the ring and challenged any tag team. Paul London and Brian Kendrick answered the challenge, only to be brutally attacked by The Gymini (Jake and Jesse), two alleged users of The Simon System. Dean began managing the team, but the team soon faded off television after Jesse suffered an injury in May 2006 and Dean went back to jobbing to other superstars.
On Friday, August 31, 2007, Dean was released from WWE.