Wrestling as Scotty the Body, Raven made a one-off appearance on WWF Prime Time Wrestling in a losing effort against Koko B. Ware in October 1990.
In 1992, he joined World Championship Wrestling (WCW). He was given the ring name Scotty Flamingo and the gimmick of a surfer from Florida, even carrying a surfboard to the ring. He was originally managed by J.T. Southern. Flamingo competed in the WCW light heavyweight division, winning the WCW Light Heavyweight Championship from Brian Pillman on June 20, 1992 at Beach Blast. He held the title until July 5, 1992, when he was defeated by Brad Armstrong.
Flamingo went on to align himself with Diamond Dallas Page and Vinnie Vegas as a member of "The Diamond Mine". Flamingo would continue to feud with Pillman and Armstrong, before feuding with Johnny B. Badd. At Clash of the Champions XXI on November 18, 1992, Flamingo defeated Badd in a boxing match via knockout after Vegas surreptitiously weighted his boxing glove by soaking it in water. Flamingo left WCW in February 1993.
After leaving WCW, Flamingo joined the World Wrestling Federation (WWF) as manager Johnny Polo, a spoiled, rich preppy kid. He was initially placed with Adam Bomb, appearing for the first time on the May 24, 1993 episode of WWF Raw. He managed Bomb for four months until he was replaced by Harvey Wippleman. He then became the manager of The Quebecers in September, whom he led to three reigns as WWF Tag Team Champions. In addition to managing, Polo also occasionally appeared in tag-team and singles competition, facing Jim Powers, Virgil, Rick Steiner, Marty Jannetty, Doink the Clown, 1-2-3 Kid, Owen Hart, and Pierre Oullette. Polo also worked as a color commentator and co-host of Radio WWF. He left the company in October 1994, with his final match coming against Adam Bomb on October 2 in Auburn Hills, Michigan. His last appearance was at a house show in Montreal, Quebec on October 21, when he managed Pierre Oullette in a match against Jacques Rougeau.
After leaving the WWF, Polo began developing a new character, Raven. The Raven character was a depressed, sociopathic, stoical, nihilistic misanthrope who would deliver eloquent, philosophical promos peppered with literary allusions and ending with the catchphrase, "Quote the Raven 'Nevermore'". He dramatically altered his appearance, bulking-up to approximately 235 pounds, adding nose and eyebrow piercings and began wrestling in ragged jean shorts, a leather jacket, rock band or comic book t-shirts, combat boots and a flannel tied around his waist.
Raven was introduced to Extreme Championship Wrestling (ECW) by Stevie Richards. In late 1994, Richards had developed an "identity crisis", performing under the ring names "Stevie Flamingo", "Stevie the Body", and "Stevie Polo". After sustaining another loss to Tommy Dreamer, Richards became irate and claimed he would present "the real Johnny Polo". Raven made his first appearance on the January 10, 1995 episode of ECW Hardcore TV, with Richards revealing that he had a vendetta against Tommy Dreamer.
Raven formed a stable of lackeys known as "Raven's Nest", with Richards the first member. In February, Johnny Hotbody and Tony Stetson joined the stable, calling Raven the "voice of their generation". On the March 24, 1995 episode of ECW Hardcore TV, Dreamer lost to the four members of Raven's Nest in a gauntlet match.
On April 8, 1995 at Three Way Dance, Raven fired Hotbody and Stetson, replacing them with The Pitbulls. Later that evening, Raven expounded on his history with Dreamer, revealed that they had attended summer camp together as children, where Raven became the boyfriend of Beulah McGillicutty, an overweight girl with acne, after she was spurned by Dreamer. Richards then revealed that he had tracked down McGillicutty, who was now a Penthouse model, who also harbored a grudge against Dreamer. Later that night, Raven faced Dreamer in a singles match for the first time, defeating him following interference from both Richards and McGillicutty. McGillicutty went on to become Raven's valet and onscreen girlfriend, repeatedly interfering in his bouts with Dreamer and receiving numerous piledrivers as a result. The feud between Raven and Dreamer escalated on the June 20, 1995 episode of ECW Hardcore TV, with Raven's Nest beating down Dreamer's ally, Luna Vachon, before breaking several of Dreamer's fingers. On June 30, 1995, Raven and Richards defeated The Public Enemy to win the ECW World Tag Team Championship.
In July 1995 at Hardcore Heaven, after Raven and Richards successfully defended the ECW Tag Team Championship against Dreamer and Vachon, The Pitbulls left Raven's Nest, with The Dudley Brothers replacing them shortly thereafter. At Heat Wave on July 15, 1995, Dreamer and The Pitbulls defeated Raven and The Dudley Brothers. Later that evening, Dreamer handcuffed Raven and delivered a chair shot later dubbed "the chair shot heard 'round the world." At Wrestlepalooza on August 5, 1995, during an 8-man tag team match, Raven, Richards and the Dudley Brothers defeated Tommy Dreamer, Cactus Jack and the Pitbulls after Cactus Jack, Dreamer's long-time ally, turned on him, joining Raven's Nest. On September 16, 1995 at Gangstas Paradise, Raven and Richards lost the ECW World Tag Team Championship to The Pitbulls following interference from Dreamer. Raven and Richards regained the titles from The Pitbulls on October 7, 1995, only to lose them to The Public Enemy later that evening. At November to Remember on November 18, 1995, Dreamer and Terry Funk defeated Raven and Cactus Jack in the main event. At the same event, Raven's Nest received a new member, The Blue Meanie, who became a lackey to Stevie Richards.
At December to Dismember on December 9, 1995, Raven once more defeated Dreamer, although later that night Dreamer, The Pitbulls and The Public Enemy defeated Raven, Richards, The Eliminators and The Heavenly Bodies in a "Ultimate Jeopardy" cage match when Dreamer pinned Richards. At Holiday Hell on December 30, 1995, Raven defeated Dreamer to become number one contender for the ECW World Heavyweight Championship, unsuccessfully challenging incumbent champion The Sandman later that evening. At the same event, The Dudley Brothers left Raven's Nest following a confrontation with Richards. During the build-up to the match, Raven further expounded on his grudge against Dreamer, accusing Dreamer of not having been there for him during his parents' divorce, an accusation that Dreamer hotly denied. At House Party on January 5, 1996, Richards attempted to kiss McGillicutty, who refused, eventually announcing that she was pregnant. After Raven angrily confronted McGillicutty, she informed him that he was not the father, causing Raven to attack Richards. McGillicutty then revealed that Tommy Dreamer was the father, with Dreamer storming the ring and beating down Raven, Richards and The Blue Meanie before embracing Beulah.
On January 27, 1996, Raven introduced his new girlfriend, Kimona Wanalaya. Later that evening, Raven defeated The Sandman to win his first ECW World Heavyweight Championship following extensive interference from Raven's Nest. Over the following months, Raven successfully defended the ECW World Heavyweight Championship in bouts with opponents including Shane Douglas, Pitbull 2, Chris Jericho, Damián, 2 Cold Scorpio and Terry Gordy.
At Hardcore Heaven on June 22, 1996, Raven began playing mind games with The Sandman, brainwashing his ex-wife, Lori and his son, Tyler to join Raven's Nest. Lori and Tyler subsequently began accompanying Raven to ringside for his matches, with Raven using him to wage psychological warfare against The Sandman over the following months.
At the High Incident event on October 26, 1996, Richards was involved in one of ECW's most controversial angles, with Raven's Nest "crucifying" The Sandman by tying him to a cross and placing a crown made of barbed wire on his head. At the instruction of Paul Heyman, Raven came to the ring and offered a somewhat insincere apology for his actions.
The relationship between Raven and Richards began to deteriorate in late 1996. At Ultimate Jeopardy on October 5, 1996, Raven was scheduled to team with Brian Lee against Dreamer and The Sandman in a match with Raven's ECW World Heavyweight Championship on the line. After Raven was announced as being unable to compete, Richards substituted for him, with Raven losing his title after The Sandman pinned Richards. Upon his return, Raven blamed Richards for the loss. At Holiday Hell on December 7, 1996, Raven defeated The Sandman in a barbed wire match to regain the ECW World Heavyweight Championship. Despite this, the tension between Raven and Richards continued to build until, on December 28, 1996, Richards turned on Raven by superkicking him during a match with The Sandman. Richards, The Blue Meanie and Super Nova subsequently broke away from Raven.
At the Crossing the Line Again event on February 1, 1997, Raven successfully defended the ECW World Heavyweight Championship against "Dr. Death" Steve Williams after interference from Richards backfired. As part of an agreement between ECW and the World Wrestling Federation, Raven and several other ECW wrestlers appeared on the February 24, 1997 episode of Raw is War, with Raven confronting Richards.
Over the following months, Raven successfully defended the ECW World Heavyweight Championship against opponents including Dreamer, Richards, Rob Van Dam and Super Nova. His reign lasted until April 13, 1997, when he was defeated by Terry Funk in the main event of Barely Legal, ECW's first pay-per-view.
On the May 1, 1997 episode of ECW Hardcore TV, a controversial angle took place in which a morose Raven, despondent at the loss of his title and other setbacks, confronted Richards, telling him he had one final "mission" for him. Raven then attacked Richards before begging him to "end my pain". At The Buffalo Invasion event on May 11, 1997, Raven and Richards reformed their tag team to face Dreamer and Funk, with Richards pinning Funk despite bickering with Raven throughout the match. In the main event, Raven, Richards, Funk and The Sandman faced one another in a four-way elimination match for Funk's ECW World Heavyweight Championship. During the match, Raven DDT'ed both Funk and The Sandman and then demanded that Richards pin them and then lay down for him. Richards refused, instead superkicking Raven and enabling Funk and The Sandman to pin him.
At Wrestlepalooza on June 6, 1997, Raven faced Dreamer in a "Loser Leaves ECW" match. During the bout, Raven abandoned his new valet, Chastity, and unsuccessfully begged Beulah to take him back. Dreamer ultimately won the match by pinning Raven for the first time, marking the end of their lengthy feud and the end of Raven's ECW career. Raven subsequently left ECW and rejoined World Championship Wrestling.
On June 30, 1997, Raven made his return to WCW. He was seen sitting in the front row at Monday Nitro, where the commentators acknowledged him as "a man who has been a champion with other organizations". On August 21, 1997, at Clash of the Champions XXXV, Raven defeated Stevie Richards in an "unsanctioned" match and then took a seat in the front row. The storyline continued that Raven would frequently appear in the front row for the next few months with his lackeys, slowly forming what would be known as The Flock. Raven was an "unsigned free agent", but eventually accepted a contract with WCW Commissioner James J. Dillon, which stipulated that he could wrestle only when he wanted and under his own rules. The Flock was a stable of misfits in the same vein as the Raven's Nest group in ECW. With The Flock, however, Raven was more openly abusive and controlling, which eventually led to dissension and rebellion. The group's matches were held under Raven's Rules, which meant no disqualifications — weapon usage, double teaming, and outside interference were rampant.
Raven made his in-ring Nitro debut on October 27, 1997, defeating Scotty Riggs. He would first offer Riggs to become a member of The Flock which Riggs would refuse. On November 23 at World War 3, Raven met Riggs again in a match, and later joined The Flock. With The Flock's help, Raven won the WCW United States Heavyweight Championship as well as the WCW World Tag Team Championship with Perry Saturn. The former reign lasted only a day as Raven defeated Diamond Dallas Page at Spring Stampede and lost the belt the following night to Bill Goldberg on Nitro. He blamed The Flock and Saturn in particular for his loss. This led to a series of matches, culminating in a match at Fall Brawl that if Raven lost, The Flock would be able to disband. Saturn won with the help of Kidman, who also wanted to leave Raven's abuses.
Without The Flock, Raven began a series of depressing interviews and walked out on several matches. In October at Halloween Havoc, Raven refused to wrestle Chris Jericho for the WCW Television Championship, but eventually was convinced to return to the ring. He lost the match and was not seen until 1999. Upon his return, a series of vignettes were shown in which a camera crew followed Raven to his supposed childhood home, where he had led a privileged upper class lifestyle. He was also reunited with his former valet Chastity, who WCW claimed was his sister.
He later joined with Vampiro and the Insane Clown Posse in a short-lived stable called The Dead Pool. In August 1999, Raven was released by WCW.
Raven made a surprise return on ECW's debut on TNN and won the ECW Tag Team Championships from the departing Dudley Boyz along with Tommy Dreamer on August 26, 1999. A reluctant tag team, Raven and Dreamer reigned as ECW World Tag Team Champions for several months. When they lost the belts, they feuded briefly. Raven and Mike Awesome won the Tag Team Titles from Masato Tanaka and Dreamer on March 4, 2000, only to lose them a week later to The Impact Players at Living Dangerously. CyberSlam 2000 was Raven's last ECW appearance with Francine, as she aligned with Justin Credible that evening. His last televised match was against Scotty Anton, which Raven lost. Shortly thereafter, he departed for the WWF.
Raven returned to the WWF in 2000, at Unforgiven, when he interfered in the strap match between Tazz and Jerry Lawler, by hitting Lawler with a DDT. His previous run in the WWF as Johnny Polo was ignored by the company. He then started teaming with Tazz before they went their separate ways. He then moved on to the Hardcore division, where he would often bring out a shopping cart full of trash cans and other potential weapons during his entrances. On December 22, 2000, in Chattanooga, Tennessee, he defeated Steve Blackman for the Hardcore Championship, his first of a record 27 title reigns, though most of Raven's title reigns were short-lived. The Hardcore Title at the time was contested under the "24/7" defense rule, leading to segments where one wrestler would win the title only to immediately lose it to another wrestler. At WrestleMania X-Seven, he competed in his only WrestleMania match, losing the Hardcore Championship to Kane in a triple threat match that also included Big Show. At Backlash, he lost to Hardcore Champion Rhyno in a hardcore match. A brief angle had an anonymous Black Ninja, who was later revealed to be Tori, aiding Raven in retaining the Hardcore Championship.
When the Invasion storyline began, he found himself in the new WCW/ECW Alliance. His most notable storyline during this time was when he was managed by Terri Runnels and destroyed the love interest of Saturn, his mop called "Moppy." He also started teaming with Justin Credible in late July 2001. By the end of the year, Raven was not seen on WWE programs, as the Alliance lost the "Winner Take All" match at Survivor Series.
In March 2002, when the WWE brand extension was announced, Raven was drafted to Raw. On the final SmackDown! before the split began, he defeated Maven to once again win the Hardcore Championship, thus bringing the title to Raw. He lost the title that Monday to Bubba Ray Dudley. At that time, Raven decided to spend some time announcing, and he became the new color commentator for Sunday Night Heat and Excess. This role lasted a couple of months, as he later quit the show to resume his wrestling career on Raw. This did not last long either, as he was banished from Raw after losing a match to Tommy Dreamer on June 24, 2002. Raven was forced to spend the rest of the year on Heat. Raven was then involved in a storyline related to the seven deadly sins, with Raven becoming a sort of "puppet master" using Heat as his playground. It started to play out; however, the angle was eventually aborted. Although he won his way back onto the Raw roster, he lost to Jeff Hardy in a Royal Rumble qualifier match in what would be his final match in the WWE. He was released from the promotion the following week on January 20, 2003.