Hall was brought in, under his real name, to the National Wrestling Alliance's World Championship Wrestling (WCW) territory by Jim Ross in 1989, when the NWA was beginning to focus on developing new, young superstars such as Brian Pillman and Sid Vicious. His first and only pay-per-view appearance during this time was at The Great American Bash: The Glory Days, which saw Hall participate (unsuccessfully) in a King of the Hill battle royal. Hall made little impact during this run and soon after he began jobbing regularly, after which he went on hiatus.

Hall made a brief stint in 1991 in the Puerto Rican promotion World Wrestling Council (WWC). On March 3, he defeated Miguel Pérez, Jr. for the WWC Caribbean Heavyweight Championship, holding it for one month before losing the title to Super Medic III on April 20.

Hall returned to the NWA in 1991, although by then the region was known as World Championship Wrestling (WCW).[14] He was named The Diamond Studd, whose gimmick was similar to Ravishing Rick Rude's with the added element of a monster big man heel, and he was managed by Diamond Dallas Page.[14] He squashed Tommy Rich in his debut on the June 14 edition of Clash of the Champions,[15] and he defeated Tom Zenk at The Great American Bash.[16]He received a significant push in his early days with WCW, but by the end of 1991 this began to fade, starting with the September 2 edition of Clash of the Champions, where Studd was defeated by Ron Simmons.[17] At Halloween Havoc: Chamber of Horrors, the team of Studd, Abdullah the Butcher, Cactus Jack, and Big Van Vader lost to Sting, El Gigante, and the Steiner Brothers (Rick and Scott).[18] On the November 19 edition of Clash of the Champions, Studd lost to Zenk in a rematch from The Great American Bash.[19]In 1992, he formed short-lived tag teams with Vinnie Vegas and Scotty Flamingo during his time in the Diamond Mine stable, while also teaming with members of Paul E. Dangerously's Dangerous Alliance.[14] The idea of adding him to the Dangerous Alliance fell through, however, and he left WCW shortly after.[14]

Hall signed a contract with the World Wrestling Federation (WWF) in 1992 and his character evolved from Scott Hall to that of Razor Ramon, a Cuban American from Miami. The Latino-heel persona was modeled after Tony Montana and Manny Ray (Al Pacino and Steven Bauer's characters from the movie Scarface). Hall's nickname (The Bad Guy) and catchphrase ("Say hello to The Bad Guy") derive from quotes from the movie; "Say hello to my little friend" and "Say goodnight to the bad guy". Later in his career, Hall claimed he pitched the idea of a Scarface-like character during a meeting with Vince McMahon and Pat Patterson, as a joke. Hall quoted lines with a Cuban accent and gave ideas for vignettes (also inspired by the movie) that would involve Hall recreating several scenes, such as Ramon driving around South Florida in a convertible with a leopard-skin interior. Although his pitch was taken right from the film, Hall claims McMahon and Patterson were nevertheless floored by the ideas and called Hall a "genius." Hall later learned that neither McMahon nor Patterson had ever seen or heard of the movie; thus, they believed that Hall was coming up with the ideas right then and there.

Hall's WWF debut was preceded by his vignettes, with his in-ring debut coming on the August 8, 1992 edition of Superstars, defeating local jobber Paul Van Dow with his finishing move, the Razor's Edge (Hall had used the finisher in his run in WCW). Early on, Ramon would wear large gold chain necklaces to the ring; upon handing them to an attendant at ringside he would threaten "Something happens to this, something gonna happen to you."

Hall's first major angle began on the September 14 edition of Prime Time Wrestling, where Ramon interfered in a WWF Championship match between the champion Randy Savage and the challenger Ric Flair. Ramon helped Flair win the title after attacking Savage on the floor. As a result, Ramon and Savage started a feud with each other, which then went on to include the Ultimate Warrior after Warrior saved Savage from a post-match beating by Ramon. Ramon and Flair were scheduled to face the Ultimate Maniacs (Savage and Warrior) at the Survivor Series, however Warrior was fired from the WWF prior to the event and was replaced by Flair's executive consultant, Mr. Perfect, who had made a face turn. At Survivor Series, Ramon and Flair went on to lose to Savage and Perfect after being disqualified by the referee for constantly double-teaming their opponents.

WWF Champion Bret Hart was scheduled to defend his title against the Ultimate Warrior at the Royal Rumble, but the Warrior's departure from the WWF left Hart without a challenger, and Razor Ramon replaced him. During the feud, Ramon continued his heel persona by disrespecting Hart and the Hart wrestling family. Like his previous attempts to win the AWA Championship in the late 1980s, Ramon was unable to defeat Hart at the Royal Rumble, submitting to the Sharpshooter. Ramon won a 16-man battle royal the following month after Giant González—who was not a participant in the match—entered the ring and eliminated Tatanka and El Matador. Ramon made his WrestleMania debut at WrestleMania IX, defeating former WWF Champion Bob Backlund with a roll-up.

Ramon defeated Tito Santana to qualify for the King of the Ring tournament in 1993, but lost in the quarterfinals to the eventual tournament winner and the man he lost to at the Royal Rumble, Bret Hart. On the May 17 edition of Monday Night Raw he had an upset loss to jobber "The Lightning Kid" (who would later gain the nickname the "1-2-3 Kid" following the upset). As a result, a small feud between himself and the 1-2-3 Kid began; it carried with him into the King of the Ring tournament; and it also began a slow face turn for Ramon, who had gained both respect for The Kid and support from the crowd. Ted DiBiase, however, did not show respect for Ramon and instead began making fun of Ramon for losing to such a small jobber. Ramon's face turn was solidified after helping the 1-2-3 Kid defeat DiBiase. The feud culminated in a match at SummerSlam, where Ramon defeated DiBiase in DiBiase's final WWF match before going to Japan.

On the October 4, 1993 edition of Monday Night Raw, a 20-man battle royal for the vacant WWF Intercontinental Championship was held; the last two participants would face other the following week for the title. Ramon and Rick Martel were the final two.[3][30] The next week on Raw, Ramon came out on top following a Razor's Edge to win the vacant Intercontinental Championship.[31] Ramon would go on to have successful defenses against the likes of Martel and Irwin R. Schyster (IRS).[20] At Survivor Series, Ramon teamed with Marty Jannetty, Randy Savage, and the 1-2-3 Kid to take on the team of Martel, IRS, Adam Bomb, and Diesel. Razor, captaining his team, went on to eliminate the opposing captain, IRS, after scoring a pin following a Razor's Edge. Although he was later eliminated from the match after being counted out when IRS hit him with his briefcase, Razor's team went on to win the match, beginning a feud between the two captains. Ramon's feud with IRS culminated at Royal Rumble where he defeated IRS to retain the Intercontinental title following the Razor's Edge.[32][33]At the same time, Ramon was in the early stages of a feud with Shawn Michaels over who had the real claim to the Intercontinental champion. Michaels had been stripped of the title months before due to "inactivity" (he was actually on suspension at that time), but began appearing on television with his own version of the belt, claiming he had never been beaten for it.[32] Their feud was showcased with Ramon defending the Intercontinental Championship against Michaels in a ladder match at WrestleMania X, where Ramon retained the championship after retrieving both belts.[34] This match was voted Pro Wrestling Illustrated's Match of the Year in 1994.[32] It was also the first WWF match to receive a five star rating from Dave Meltzer of the Wrestling Observer Newsletter.[32] On, this match is rated as the #5 match in the top 22 matches in WrestleMania history.[35] Ramon continued to feud with Michaels and his bodyguard Diesel and on the April 30 edition of Superstars, he dropped the Intercontinental Championship to Diesel after interference from Michaels.[36]Ramon would then go on to defeat Kwang to qualify for the King of the Ring tournament in 1994.[32] At King of the Ring, he defeated Bam Bam Bigelow in the quarterfinals of the tournament[37][38] and Irwin R. Schyster in the semifinals,[37][38] before a loss in the finals of the tournament to his old rival Bret Hart's younger brother, Owen.[37][38] At SummerSlam, Ramon (with Walter Payton in his corner) defeated Diesel to win his second WWF Intercontinental Championship after Shawn Michaels accidentally hit Diesel with Sweet Chin Music.[39][40] At Survivor Series, he captained a team dubbed "The Bad Guys" consisting of himself, the 1-2-3 Kid, Davey Boy Smith, and The Headshrinkers (Fatu and Samu) against The Teamsters (Shawn Michaels, Diesel, Owen Hart, Jim Neidhart, and Jeff Jarrett). Ramon ended up as the sole survivor of the match and by the end of 1994, he began a feud with Jeff Jarrett which led into the next year.[32][41]At the Royal Rumble in 1995, Ramon lost the Intercontinental Championship to Jarrett, although the match ended in controversial fashion; Jarrett had originally won the match by count-out, but demanded that the match be restarted so he could win the title. Jarrett then pinned the champion with a small package.[42][43] He faced Jarrett in a rematch for the Intercontinental Championship at WrestleMania XI. Ramon won the match by disqualification after Jarrett's assistant The Roadie interfered; thus, Jarrett retained the title as a title cannot change hands by count-out or disqualification.[44] Ramon later defeated Jarrett and Roadie at In Your House 1 in a handicap match.[45] On May 16, Razor qualified for the King of the Ring tournament by defeating Jacob Blu.[43] He later defeated Jarrett in a ladder match on May 19, 1995 at a live event to win his third WWF Intercontinental Championship.[46] At that time, this was a record because Ramon was the first man to hold the Intercontinental title three times.[46] Three days later on May 22, he lost the title back to Jarrett.[46] and on June 9, Ramon suffered a rib injury during a ladder match rematch against Jarrett.[43] During this time, he formed a team with Savio Vega, and Vega defeated Irwin R. Schyster in the Free for All match at the pay-per-view to fill Razor's vacancy.[43] Razor managed Vega throughout the tournament, who ultimately lost to Mabel in the finals.[43]Razor and Vega lost to Men on a Mission (Mabel and Mo) at In Your House 2: The Lumberjacks,[47] and a Tag Team Championship match against Owen Hart and Yokozuna on the August 7 edition of Raw.[48] Razor received an Intercontinental title ladder match against the new champion Shawn Michaels at SummerSlam, in what was considered to be their WrestleMania X rematch.[1][9][43] Razor went on to lose the match against Michaels,[49] and then started a feud with Dean Douglas. Ramon defeated Douglas at In Your House 4 for the Intercontinental Championship. Michaels had just forfeited the title to Douglas.[50][51]In early 1996, Ramon started a feud with newcomer Goldust, leading to an Intercontinental title match at the Royal Rumble. Ramon lost the title to Goldust after Ramon's former partner the 1-2-3 Kid (who had previously made a heel turn) cost him the match.[52] He became a member of the WWF's off-stage The Kliq which consisted of Kevin Nash (Diesel), Paul Levesque (Hunter Hearst Helmsley), Michael Hickenbottom (Shawn Michaels), and Sean Waltman (1-2-3 Kid).[53] Razor was originally scheduled to face Goldust in a rematch for the title at WrestleMania XII, but had been suspended by the WWF in the weeks prior due to drug abuse.[53] He was not seen on WWF television again until April's In Your House 7 where he jobbed to Vader.[54] Hall was also a participant in the MSG Incident. As Hall and fellow Kliq member Kevin Nash were departing for WCW, the pair along with Hickenbottom and Levesque broke kayfabe, celebrating and embracing in the ring together.[53]

Hall's first appearance on May 27, 1996 on WCW television after leaving the WWF was an unannounced interview where he appeared from the crowd in street clothes, claiming to be "an outsider." He was then joined in the following weeks by Kevin Nash, the two claiming they were going to undertake a hostile takeover of WCW. The angle directly paralleled the real-life competition between WCW and the WWF. At the following pay-per-view, Bash at the Beach, Nash and Hall known as The Outsiders, along with a mystery partner, took on Sting, Lex Luger, and Randy Savage. The mystery partner turned out to be Hulk Hogan, and the three formed the New World Order (nWo). The stable stormed WCW, enlisting such stars as Syxx (Kliq member Sean Waltman), The Giant, and Buff Bagwell.

Hall and Nash closed out 1996 with victories over Sting and Lex Luger at Hog Wild, and WCW's WarGames match at Fall Brawl. They defeated Harlem Heat (Booker T and Stevie Ray) at Halloween Havoc for their first WCW World Tag Team Championship. They successfully defended the titles against The Nasty Boys (Brian Knobbs and Jerry Sags) and Faces of Fear (The Barbarian and Meng) at World War 3, and then again defeated the Faces of Fear at Starrcade. The duo would hold the WCW World Tag Team title from February 24, 1997 to October 13, 1997, often feuding with the Steiner Brothers (Rick and Scott), Lex Luger and the Giant, and the Four Horsemen. Since Eric Bischoff was a member of the nWo, he used his power to return the title to the Outsiders on a technicality whenever they lost them. The Outsiders would also use the Freebird Rule to defend their title. With Nash and Syxx out with injuries, Hall used the last quarter of 1997 to focus on singles wrestling. Hall was defeated by Luger in a grudge match at Halloween Havoc via submission with Larry Zbyszko serving as the guest referee. One of Hall's greatest achievements in WCW was winning the 60 man battle royal at World War 3 1997 earning a shot at the WCW World Heavyweight Championship.

On the January 12, 1998 edition of Nitro, Hall and Nash defeated the Steiner Brothers for their second WCW World Tag Team Championship. Hall eventually wrestled Larry Zbyszko at Souled Out but lost by disqualification. The Outsiders lost the tag title back to the Steiners on the February 9 edition of Nitro. At SuperBrawl VIII, the Outsiders won their third WCW World Tag Team Championship by defeating the Steiner Brothers. At Uncensored, Hall got his title shot against Sting for the World Heavyweight Championship as a result of winning World War 3, and lost the match, despite interference from Dusty Rhodes. He would then be taken off TV for a short while in early 1998 in a show of power by WCW President Eric Bischoff as a way to keep Hall and Nash in check. While Hall was absent, the nWo split into two warring factions. Still one half of the tag team champions with Kevin Nash, the thought was that Hall would return alongside his friend in the nWo Wolfpac.

At Slamboree, Hall returned to team with Kevin Nash in a title defense against Sting and The Giant. In a swerve, Hall turned on Nash, costing them the title and jumping sides to align himself with Hulk Hogan in nWo Hollywood.[62][64][65] On the July 6 edition of Nitro, a returning Scott Hall was handpicked by Hogan to wrestle United States Champion Bill Goldberg.[62] Hall lost the match, setting the stage for Hogan to be defeated later that night by Goldberg for the World Heavyweight Championship.[62] Hogan publicly blamed Hall for the loss and Hall was seen as a weak link by the rest of the nWo, especially Scott Steiner.[62]On July 13, Hogan challenged Hall to a match on Nitro. Hall accepted the challenge and it looked like Hall had finally gotten sick of being ordered around by Hogan and his lackeys.[62] However, Nash interfered during the match.[62] As he was about to Jacknife Powerbomb Hogan and regain Hall as his friend, Hall viciously attacked Nash, proving his allegiance to Hogan and nWo Hollywood.[62] In the following weeks, Hall mocked Nash calling himself "Medium Sexy (later "Super Sexy"), the Nash Killer."[62] On the July 20 edition of Nitro, Hall won his fourth WCW World Tag Team Championship with The Giant,[6] as they defeated Sting and Nash due to outside interference from Bret Hart, who was in the midst of a rivalry with Sting at the time.[62] This title reign would come to an end at Halloween Havoc, when Rick Steiner defeated The Giant and Scott Steiner (who replaced Hall) to claim the title even after partner Buff Bagwell turned on him.[62]Scott Hall's character became out of control and would bring alcohol to the ring, and his behavior on TV mirrored his real-life problems with drugs and alcohol. This had him once "vomit" on Eric Bischoff, and in another vignette, Kevin Nash along with WolfPac members Konnan and Lex Luger, followed Hall to a local bar where Hall and Nash had a physical confrontation. On October 7, Hall's ex-wife Dana wrote an open letter "to anyone who cares". In the letter, she admonished World Championship Wrestling and Eric Bischoff for not only failing to rehabilitate him but coming to the point where they were exploiting, humiliating, and even enabling him to continue his self-destructive behavior. She accused WCW of allowing Hall to perform while under the influence, and taking advantage of his real addictions to drugs and alcohol for profit and ratings. She called the angle "deplorable, disgusting, and inexcusable". She pleaded with WCW to discontinue the controversial angle for the sake of Hall's two children, whom she said he had no relationship with. She ended the letter by making a desperate plea to everyone to help Scott see his problems and "put himself in God's hands". She said Hall remained a very sick man and his addictions had destroyed his marriage, his future, and his children's future.[66]Hall and Nash eventually faced each other on October 25 at Halloween Havoc. After hitting Hall with two Jackknife Powerbombs, Nash left the ring and lost the match by count-out in what was seen as an act of mercy.[62][67] Hall was then ousted by nWo Hollywood after Steiner took control in Hogan's absence in late 1998.[62] He then referred to himself as the Lone Wolf. On November 30, 1998, Hall needed a tag partner to face the team of Steiner and Horace Hogan. Initially, Hall said he would do it alone, but Kevin Nash came to the entrance and told Hall he would tag with him. Together the team, formerly known as the Outsiders, won the match. At Starrcade, Hall disguised himself as a security staff member and used a stun gun on WCW Champion Goldberg during his title match with Kevin Nash. Having not seen the interference, Kevin Nash jackknifed and covered Goldberg to become the WCW Champion and break Goldberg's winning streak.[62]

It seemed Nash and Hall were seeing eye to eye again, and it all came to a head in January 1999 when the two nWo factions rejoined. Scott Hall feuded with Goldberg and faced him in a "Ladder Taser match" on January 19 at Souled Out. Hall lost the match when Goldberg used the taser gun on Hall. At SuperBrawl IX, Hall defeated Roddy Piper for the WCW United States Heavyweight Championship. Shortly after, Hall suffered a foot injury forcing him to forfeit the title. Hall would not be seen again until October 1999 when he and Kevin Nash began sitting at ringside during WCW television, proclaiming that "the band was getting back together." On the November 8 edition of Nitro, Hall defeated Goldberg, Bret Hart, and Sid Vicious in a Texas Tornado ladder match to win his second United States Heavyweight Championship. Two weeks later at Mayhem, he defeated Rick Steiner by forfeit to win the WCW World Television Championship, therefore becoming a double champion. He successfully defended both titles against Booker T later that same night.

Hall, however, vacated the TV title by throwing it into a trash can eight days later on Nitro. Hall's U.S. title was soon stripped due to a knee injury and awarded to Chris Benoit. Hall and Nash would eventually team up to defeat Bret Hart and Bill Goldberg on the December 13 edition of Nitro for their sixth WCW World Tag Team Championship as a team. Yet soon afterwards, Hall's personal problems arose again and the tag team title was stripped from the Outsiders. After the nWo returned in December 1999, Hall soon joined teammates Kevin Nash, Bret Hart, Jeff Jarrett, and Scott Steiner in what was coined "nWo 2000." As 2000 came along, Scott Hall got involved in a feud with WCW World Heavyweight Champion Sid Vicious and nWo teammate Jeff Jarrett for the WCW title. Sid pinned Hall in a match also involving Jarrett at SuperBrawl on February 20. This pay-per-view appearance was Scott Hall's last, and it ended his stint in WCW. In total, Hall won seven World Tag Team Championships, one World Television Championship and two United States Heavyweight Championships.

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