In late 1993, Dean made several appearances in the World Wrestling Federation, wrestling in tag team matches against the Steiner Brothers and the Headshrinkers on Monday Night Raw.
In 1995, Dean debuted in Extreme Championship Wrestling (ECW) as Nova, utilizing a superhero character. He was paired with Raven, Stevie Richards, and The Blue Meanie as part of the Raven's Nest faction.
Nova, along with Richards and Blue Meanie, formed The Blue World Order (bWo), a parody of WCW's New World Order (nWo) faction. Nova parodied Hollywood Hogan as Hollywood Nova, Richards became "Big Stevie Cool" (a takeoff on Kevin Nash's nickname of "Big Daddy Cool"), and Meanie was "Da Blue Guy", a takeoff on Scott Hall, "The Bad Guy". Many other members were added and removed between 1996 and 1998 before the team split in the latter. Richards left the bWo to return to Raven's Nest, and Nova and Meanie continued to team together. They started a feud with the much larger stable Full Blooded Italians. They also briefly feuded with Danny Doring and Roadkill, defeating them at November to Remember 1998.
After Meanie left the company, Nova changed his gimmick, becoming Super Nova, and adopting a more serious personality. He formed a tag team with Chris Chetti, as well as a briefer one with Kid Kash. In late 2000 through early 2001, Nova and Chetti broke up as a team and started a heated rivalry, with Nova beating his former partner in a match where the loser was fired at November to Remember.
Nova's last televised appearance in ECW was at their last pay-per view, Guilty as Charged. At the second to last ECW event in Poplar Bluff, Missouri, he was named as Danny Doring's substitute tag team partner (filling in for Amish Roadkill) to help defend the ECW World Tag Team Championship against Hot Commodity; Doring and Nova successfully defended the titles.
In August 2004, a series of introductory promos about the "Simon System" (a program of diet, exercise, and supplements) were aired on WWE television. The promos parodied fitness infomercials, with Nova, now known as Simon Dean, routinely insulting 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 the Raw brand, 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 the WWE produced ECW pay-per-view, One Night Stand, Dean returned 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 six-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 Dean 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 Nova 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. On the September 1 episode, he faced Batista, whom he claimed to be a user of his products. 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 twenty double cheeseburgers, causing him to vomit backstage.
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 Gymini (Jake and Jesse), two alleged users of The Simon System. Dean was the third entrant in the 2006 Royal Rumble, but was eliminated quickly by Triple H and Rey Mysterio. Dean began managing Gymini, 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 August 31, 2007, Dean parted ways with WWE.