In 1986, Douglas wrestled Randy Savage at a WWF Superstars of Wrestling taping. He also wrestled "Mr. Wonderful" Paul Orndorff in the debut episode of WWF Wrestling Challenge.
In 1989, Douglas signed with World Championship Wrestling (WCW). He was put into a tag team of skateboarders known as The Dynamic Dudes with Johnny Ace. Jim Cornette, who was managing The Midnight Express (Bobby Eaton and Stan Lane) at the time, decided to manage the duo. When Eaton and Lane in storyline did not approve, they forced a match between the two teams with Cornette remaining neutral at ringside. He ended up turning on Douglas and Ace and the teams feuded for a couple of months.
The Dynamic Dudes broke up in 1990, and Douglas soon left WCW.
In 1990, Douglas signed a deal with the World Wrestling Federation and made his debut on the June 18 episode of Prime Time Wrestling, defeating Bob Bradley, in a match taped in Toronto, Ontario on May 27. Douglas remained undefeated in his first month, defeating Bob Bradley, Paul Diamond, and Steve Lombardi in a series of matches. He then moved up to begin a house show series in late June against Haku and suffered his first loss on June 28 in Denver, Colorado. He remained without a win in subsequent rematches. He made his televised debut on the promotion's flagship show WWF Superstars on the August 26 SummerSlam pre-show, teaming with Mark Thomas in a loss to The Orient Express.
In August 1991, he received his first break when he was tapped as the temporary replacement to an injured Shawn Michaels in The Rockers tag team. Douglas teamed with Marty Jannetty six times in matches against The Orient Express. On August 27 he made his pay-per-view debut, defeating Buddy Rose in a dark match at SummerSlam. On the September 17 episode of Prime Time Wrestling, Douglas wrestled Haku to a draw, and he was largely undefeated against low level competition throughout the fall. At Survivor Series, Douglas defeated Buddy Rose in another dark match, and on January 3, 1991, at a house show in Scranton, Pennsylvania, he scored the biggest victory of his nascent WWF career when he upset Dino Bravo. Four days later on the January 7, 1991 episode of Prime Time Wrestling, he would pin Haku, and was strongly positioned as a rising young star.
His most memorable WWF performance took place at the 1991 Royal Rumble, where he entered as the seventeenth entrant and lasted for 26 minutes and 23 seconds before being eliminated by Brian Knobbs. Shortly after, left the company.
Douglas however would return to make a few intermittent appearances afterwards in 1991, subbing for various wrestlers on house shows. He returned on May 8 in Youngstown, Ohio and lost to Ricky Steamboat. In June, he returned for a pair of house shows and was defeated by Colonel Mustafa. He made his final televised appearance on the June 15 episode of Prime Time Wrestling, losing to Dino Bravo in a match taped at Madison Square Garden. Douglas closed out his first WWF run with two victories - a win on July 29 in a dark match at a WWF Superstars taping against Bob Bradley, and a victory over The Orient Express on August 2 in Pittsburgh, Pennsylvania, when he teamed with Marty Jannetty.
Douglas returned to WCW on the September 12, 1992 episode of Saturday Night as a fan favorite, where he defeated Super Invader in his return match by using Magnum T.A.'s finishing move, belly to belly suplex, which was noted by Magnum, the following week on Saturday Night. On the October 17 episode of Saturday Night, Douglas had a match with Brian Pillman, which began a rivalry between the duo. He made his pay-per-view return at Halloween Havoc, where he teamed with Tom Zenk and Johnny Gunn to compete against Arn Anderson, Bobby Eaton and Michael Hayes in a winning effort.
While feuding with Pillman, Douglas formed a tag team with Ricky Steamboat to take on Pillman and Steve Austin in a tag team match on the October 24 episode of WorldWide. The following month, Steamboat and Douglas were booked to win the WCW World Tag Team Championships from Dustin Rhodes and Barry Windham on the November 18 Clash of the Champions XXI. Steamboat and Douglas made a successful title defense against Windham and Pillman at Starrcade.
Steamboat and Douglas began a lengthy rivalry with Pillman and his new tag team partner Steve Austin. Steamboat and Douglas successfully defended the tag titles against Austin and Pillman on the January 13, 1993 Clash of the Champions XXII, before dropping the titles to Austin and Pillman on the March 27, 1993 episode of WorldWide. Soon after losing the tag titles, Douglas began a rivalry with the World Television Champion Paul Orndorff, where he came up short against Orndorff in two respective matches in the Computer Contenders Challenge on the May 1 episode of WorldWide and the May 8 episode of Power Hour, before departing the company. Douglas had been scheduled to team with Steamboat in a steel cage match for a title shot at the WCW World Tag Team Championship at Slamboree, but was replaced by Tom Zenk in a mask.
Douglas debuted for Extreme Championship Wrestling (ECW) on the August 24, 1993 episode of Extreme Championship Wrestling and solidified his status as a villain by joining Hotstuff International. In his first match, Douglas defeated Don E. Allen and Herve Renesto in a handicap match. Douglas quickly rose to the top of the roster, winning the ECW Heavyweight Championship on the September 14 episode of Extreme Championship Wrestling, after champion Tito Santana forfeited the title. Douglas successfully defended the title against The Sandman at the UltraClash event. At Bloodfest: Part 2, Douglas retained the title against J.T. Smith before dropping the title to Sabu later that night.
On the December 14 episode of Extreme Championship Wrestling, Douglas substituted for an injured Johnny Gunn to defend the ECW Tag Team Championship alongside Gunn's partner Tommy Dreamer against Kevin Sullivan and The Tazmaniac, during which Douglas turned on Dreamer by attacking him with a steel chain. The following week, Douglas defeated Dreamer via disqualification by hitting Dreamer with a steel chain and handing over the chain to Dreamer, which fooled the referee to believe that Dreamer had hit him with the chain. Douglas defeated Dreamer at Holiday Hell to end the feud.
Douglas developed a gimmick of a foul-mouthed, incredibly arrogant villain, and gave himself the nickname "The Franchise", while Sherri Martel became his valet. Douglas gained notoriety when he wrestled Terry Funk and Sabu to a one-hour draw in the company's first-ever three-way dance for the ECW Heavyweight Championship at The Night The Line was Crossed. Douglas dethroned Funk in an Ultimate Jeopardy steel cage match to win his second ECW Heavyweight Championship at Ultimate Jeopardy. Douglas closed 1994 with successful title defenses of the ECW World Heavyweight Championship against Ron Simmons.
In early 1995, Douglas formed the Triple Threat faction, aligning himself with Chris Benoit and Dean Malenko. He started the year with successful title defenses of the ECW World Heavyweight Championship against Tully Blanchard and Marty Jannetty. He then entered a feud with The Sandman during a match at Three Way Dance, where Sandman's valet, Woman, seemed to have aligned herself with Douglas by helping him in retaining the title against Sandman by handing him Sandman's Singapore cane to attack him and get the win. However, it turned out to be a ruse when she aided Sandman in defeating Douglas for the title at Hostile City Showdown. Douglas' lengthy reign ended at 385 days, which is the second longest reign in the title history.
After failing to regain the title, Douglas began a rivalry with Cactus Jack, as each man wanted to capture the title from Sandman and saw the other as competition. During this time, Douglas went on a tirade about the lawlessness of ECW and brought in Bill Alfonso as a troubleshooting referee to restore order. After teasing a departure for the WWF, Douglas finally left ECW for WWF, making his last appearance during a world title match between Sandman and Cactus Jack at Heat Wave, during which he attacked both men and left.
In 1995, Douglas returned to the WWF with a college dean character under the ring name Dean Douglas, making his first appearance on the July 29 episode of Superstars. To establish himself, he filmed several vignettes with a chalkboard, lecturing wrestlers and fans. He would also be shown taking notes of his opponents at ringside during some matches, and frequently carried a paddle (dubbed the "Board of Education") with him to the ring. He would usually present a "Report Card" in which he would degrade the performances of face wrestlers after their matches.
Douglas began a rivalry with Razor Ramon after grading him "MF" for miserable failure after Razor's loss to Shawn Michaels at SummerSlam. Douglas made his in-ring return to WWF on the September 9 episode of Superstars, where he defeated 1-2-3 Kid by disqualification after Razor attacked Douglas. This resulted in a match between Douglas and Razor at In Your House 3, which Douglas won after interference by the Kid.
He was set to wrestle Shawn Michaels for the Intercontinental Championship at In Your House 4, but Michaels forfeited the title due to injuries. Douglas, however, immediately had to defend the title against rival Razor Ramon. Ramon would go on to defeat Douglas, ending his reign at only twenty minutes. Douglas was randomly paired with Razor, Owen Hart and Yokozuna against Shawn Michaels, Ahmed Johnson, British Bulldog and Sycho Sid in a Wildcard Survivor Series match at Survivor Series. Douglas was eliminated by Michaels after Razor attacked him. His team went on to lose the match.
Douglas failed to recapture the Intercontinental Championship from Razor Ramon on the December 4 episode of Monday Night Raw. His last televised match was on the December 9 episode of Superstars, where he defeated enhancement talent Tony Williams. His last appearance on WWF television was at In Your House 5, when he was booked to wrestle Ahmed Johnson. According to the storyline, his back was not in wrestling condition, so he introduced Buddy Landel as his substitute, who was subsequently defeated by Johnson in just forty-two seconds.
After leaving the WWF, Douglas made his surprise return to ECW at the House Party event, where he reprised his Dean Douglas character, correcting Buh Buh Ray Dudley's grammar after a match, thus becoming a fan favorite. His televised return aired on the January 9, 1996 episode of Hardcore TV, where he confronted Stevie Richards and the Blue Meanie, denounced his Dean gimmick and declared "the Franchise is back!". During this time, he had a memorable feud with Cactus Jack as Cactus was getting ready to leave for the WWF and cutting promos encouraging Tommy Dreamer to side with him, deriding ECW's hardcore style and promoting clean wrestling. Douglas eventually pinned Jack in a match at CyberSlam after performing a drop toe-hold onto an opened steel chair after Jack's partner Mikey Whipwreck betrayed Jack. Upon his return, Douglas also targeted the World Heavyweight Champion Raven and received several title shots, but came up short due to heavy interference by members of Raven's Nest.
After failing in his attempts to regain the World Heavyweight Championship, Douglas won the World Television Championship from 2 Cold Scorpio at A Matter of Respect and eventually turned into a villain by showing disrespect to the title. After the match, 2 Cold Scorpio attacked him. A month later, Douglas was scheduled to defend the title against Scorpio at Fight the Power, but Scorpio was injured, which resulted in Douglas retaining the title against El Puerto Ricano, Don E. Allen, Devon Storm and Mikey Whipwreck in quick succession before losing it to Pitbull #2 after Douglas insulted The Pitbulls' manager, Francine, and gave her a belly-to-belly suplex. At Heat Wave, Douglas won his second World Television Championship by defeating champion Chris Jericho, 2 Cold Scorpio and Pitbull #2 in a four corners match, after Francine turned on them and aided Douglas in winning the match. With Francine by his side, Douglas continued to feud with Pitbull #2 and retained his title against the latter in subsequent rematches for the remainder of the year.
In the fall of 1996, Douglas reformed the Triple Threat with new members Chris Candido and Brian Lee. Douglas and Francine entered a feud with Tommy Dreamer and Beulah McGillicutty, which culminated in a series of matches between the two pairs throughout late 1996 and early 1997.
The Triple Threat feuded with Douglas' enemies Tommy Dreamer and The Pitbulls throughout the first half of 1997, while Douglas continued his successful title defenses of the World Television Championship against Pitbull #2. Douglas retained his title against Pitbull #1, as well, in an "I Quit" match at Hostile City Showdown. During this time, a mysterious man began stalking Francine and displayed mannerisms of Rick Rude. After Douglas retained his title against Pitbull #2 at ECW's first pay-per-view Barely Legal, Brian Lee revealed himself to be the mysterious stalker and delivered a chokeslam to Douglas. As a result, Lee was removed from the Triple Threat due to his betrayal and left ECW. The Triple Threat gained Bam Bam Bigelow in Lee's place, who joined the group as Douglas' partner in a tag team match against The Pitbulls at Chapter 2.
At Wrestlepalooza, Douglas retained his title against Chris Chetti. Later that night, Douglas interrupted Taz's promo after a match between Taz and Sabu. Douglas defended his title against Taz, with the stipulation that Taz would not be able to compete in ECW for sixty days. Douglas lost the title in under three minutes after Taz made him submit to the Tazmission. Douglas' reign ended at 329 days. He then turned his attention on capturing the World Heavyweight Championship from Terry Funk and challenged him for the title at Heat Wave, but lost by disqualification. Douglas received another shot on the August 14 episode of Hardcore TV, but lost. Shortly after, Sabu won the title but Douglas remained in the title picture. At Hardcore Heaven, Douglas defeated Sabu and Funk in a three-way dance to win the title for the third time. Douglas retained the title against Phil Lafon in a no disqualification match at As Good as it Gets.
Douglas lost his title to Bam Bam Bigelow on the October 24 episode of Hardcore TV after Rick Rude chose Bigelow as Douglas' challenger. As a result, Bigelow was kicked out of the Triple Threat and replaced by Lance Storm. After failing in a rematch at Ultimate Jeopardy, Douglas regained the title by defeating Bigelow at the November to Remember pay-per-view, beginning his fourth reign as champion. Douglas was injured in the match and was sidelined for nearly two months, making his return to action on January 30, 1998. At Hostile City Showdown, Bigelow rejoined the Triple Threat by turning on his partner Taz during a match against the Triple Threat. Bigelow's return lead to Lance Storm being kicked out of the group, which began a feud between Storm and the Triple Threat. At Living Dangerously, Douglas and Chris Candido faced Storm and his mystery partner, who was revealed to be Al Snow. Snow pinned Douglas following a Snow Plow. This earned Snow a title shot against Douglas for the ECW World Title at Wrestlepalooza, where Douglas retained the title.
Douglas suffered an injury which prevented him from competing for a couple of months but he continued to appear on television, during which the Triple Threat began feuding with Taz, Rob Van Dam and Sabu. The two teams squared off in a match at November to Remember, where the Triple Threat lost. After the match, Bigelow left ECW and Chris Candido abandoned Douglas, resulting in the Triple Threat being disbanded.
Douglas continued his feud with Taz, which culminated in a match between the two at Guilty as Charged in 1999, where Douglas lost the ECW World Heavyweight Championship to Taz after Douglas was attacked by former teammate Chris Candido, allowing Taz to win with a Tazmission. Douglas' fourth ECW World Heavyweight Championship reign was the longest reign in the title's history, lasting 406 days. Douglas faced Taz in a rematch for the World Heavyweight Championship at House Party, where he lost. At Crossing the Line, Douglas allied with his long-time nemesis Tommy Dreamer to feud with the Impact Players after both men claimed to be the "New Franchise", but Douglas elected Dreamer as his successor, turning Douglas face for the first time in nearly three years. At Living Dangerously, Dreamer and Douglas defeated the Impact Players. Douglas continued to feud with the Impact Players until he left the company. Douglas wrestled his last match in ECW on April 15, 1999, where he defeated Justin Credible after a Pittsburgh Plunge.
After quitting ECW, Douglas made a surprise return to WCW on the July 26, 1999 episode of Nitro, where he joined with former Triple Threat members Chris Benoit and Dean Malenko and fellow ECW alumnus Perry Saturn to form The Revolution, and pledged to cut the "cancer" out of WCW. Asya was later added to the group in place of Benoit, who left the team. The group wrestled other groups including the West Texas Rednecks, the First Family, the Filthy Animals, and the Varsity Club during its run. The group was rarely featured prominently and never really challenged the dominant wrestlers of WCW. The lack of success would eventually lead to the demise of the group after Malenko and Saturn left WCW. Following the disbanding of the Revolution, Douglas managed The Wall at the Souled Out pay-per-view in 2000, before taking a hiatus from television.
Douglas returned to WCW television on the April 10, 2000 episode of Nitro, where he aligned himself with Vince Russo and joined The New Blood group run by Russo and Eric Bischoff, which feuded with the older established The Millionaire's Club, which included his on-screen nemesis Ric Flair. Douglas faced Flair for the first time on that same night in a match, which Douglas lost by disqualification. At Spring Stampede, Douglas was paired with Buff Bagwell in a four-team tournament for the vacated WCW World Tag Team Championship, where they defeated Harlem Heat 2000 in the semi-finals and the makeshift team of Ric Flair and Lex Luger in the finals, after Brian Adams and Bryan Clark delivered a High Times. Douglas resumed his feud with Flair, which culminated in a match between the two at Slamboree, which Douglas won, with the help of Flair's son David Flair in disguise of a masked man. On the May 15 episode of Nitro, Douglas defended the WCW Tag Titles alongside The Wall, who substituted for Buff Bagwell in a match against KroniK, which KroniK won.
Douglas received an opportunity for the WCW World Heavyweight Championship against Jeff Jarrett on the May 31 episode of Thunder, where he failed to win the title after the WCW Commissioner Ernest Miller delivered a Feliner to Douglas. Douglas competed against The Wall in a best-of-five tables match at The Great American Bash, which Douglas won by driving Wall through three tables.
At Bash at the Beach, Douglas defeated his former tag team partner Buff Bagwell, by debuting his new finishing move called Franchiser and with assistance by Torrie Wilson, who turned on Bagwell. With Wilson as his manager, Douglas began using his ECW nickname "The Franchise" and delivered a promo on the microphone. Douglas participated in a tournament for the vacated United States Heavyweight Championship on the July 18 episode of Monday Nitro, where he defeated Billy Kidman in the quarter-finals but lost to eventual winner Lance Storm in the semi-finals. Douglas would begin a rivalry with Kidman, which resulted in a loss for Douglas in a strap match at the New Blood Rising pay-per-view. However, Douglas and Torrie Wilson defeated Kidman and Madusa in a scaffold match at Fall Brawl.
In the fall of 2000, Douglas became allied with the Natural Born Thrillers, during which he helped their leader Mike Sanders win a kickboxing match against Ernest Miller at Halloween Havoc, which lead to Douglas facing Miller in a match at Mayhem, which Miller won. Douglas would then enter a rivalry with Misfits in Action leader General Rection over Rection's United States Heavyweight Championship. He faced Rection for the title at Starrcade, but lost by disqualification after Chavo Guerrero, Jr. informed the referee that Douglas was trying to use a chain to hit Rection. In 2001, Douglas defeated Rection in a first blood chain match to capture the title at the Sin pay-per-view. Douglas dropped the belt to Rick Steiner on the February 5 episode of Nitro. This was Douglas' last WCW match in the company and he sat out the rest of his WCW contract until it was purchased by the WWF on March 23, 2001. After WCW closed down, Douglas did not go to the WWF.