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In the spring of 1985, the tag team of Ole Anderson and Arn Anderson began aiding Ric Flair (whom they claimed as a "cousin") in attacks against Dusty Rhodes, Magnum T.A., and Sam Houston. A few weeks later, the Andersons interrupted Houston's match against Tully Blanchard, and the three villains combined to rough up the youngster while sending a message to the rest of the NWA. Shortly thereafter, Flair, Blanchard, and the Andersons formalized their alliance, calling themselves the Four Horsemen, with Blanchard's manager J.J. Dillon also coming on board. Upon the group's inception, it was clear that the Horsemen were unlike any villainous alliance that had ever existed. The four rule breakers immediately used their strength in numbers to decimate the NWA's top fan favorites while controlling the majority of the championship titles. Over the years, there would be various incarnations of the group, with Flair and Arn Anderson as the two permanent members, while a number of different wrestlers, including Lex Luger, Barry Windham, Sting, Sid Vicious, Paul Roma, Brian Pillman, Chris Benoit, Jeff Jarrett, Steve McMichael, Curt Hennig, and Dean Malenko, have held the other two spots in the Horsemen.

By 1986, wrestling promoter Jim Crockett had consolidated the various NWA member promotions he owned into a single entity, running under the banner of the National Wrestling Alliance. Controlling much of the traditional NWA territories in the southeast and Midwestern United States, Crockett looked to expand nationally and built his promotion around Flair as champion. During this time, Flair's bookings as champion were tightly controlled by Crockett, and a custom championship belt was created for Flair. In 1987, Flair and Barry Windham had a series of matches for the NWA World Championship. Flair defeated Windham at the Crockett Cup tournament and they fought to a time limit draw in January. Flair lost the NWA World Championship due to his flamboyant ways in Detroit to Ron Garvin on September 25, 1987. Garvin held the title for two months before losing to Flair on November 26, 1987 at WCW's first pay-per-view event, Starrcade, in Chicago.

In early 1988, rising star Sting had challenged Flair to a match at the first ever Clash of the Champions. Flair accepted and fought Sting to a 45 minute time-limit draw. In late 1988, booker Dusty Rhodes proposed that Flair lose the NWA World Heavyweight Championship to Rick Steiner in a short match at Starrcade when no agreement could be met regarding the finish to the scheduled main event between him and Lex Luger. Rhodes was fired for various issues within the company, and former JCP booker George Scott was given his role as a booker. Scott immediately negotiated to bring in Ricky Steamboat for a series of matches. On February 20, 1989, at Chi-Town Rumble in Chicago, Steamboat pinned Flair to win the NWA World Heavyweight Championship. This prompted a series of rematches, where Steamboat was presented as a "family man" (often accompanied by his wife and young son), while Flair opposed him as an immoral, fast-living "ladies man". Following a best-of-three falls match with Steamboat that lasted just short of the sixty-minute time limit (and ended with a disputed finish where Steamboat retained the title) at Clash of the Champions VI: Ragin' Cajun on April 2, Flair regained the title from Steamboat on May 7, 1989 at WrestleWar. This match was voted 1989's "Match of the Year" by Pro Wrestling Illustrated. Flair was attacked by Terry Funk (serving as a judge for the match, as per its stipulations) after the match when Flair refused to grant Funk a title match, telling Funk that he had spent too much time in Hollywood and out of wrestling, and was not a listed title contender. The attack reached its conclusion when Funk gave Flair a piledriver onto the judges' table.

Months later, a "recovered" Flair returned to competition in an emotional match against Funk at The Great American Bash. The two continued feuding through the summer and eventually Flair reformed the Four Horsemen, with the surprise addition of longtime rival Sting, to combat Funk's J-Tex Corporation. This led to an "I Quit" match at Clash of the Champions IX: New York Knockout. Before the match, Funk stated that he would shake Flair's hand if he lost, a promise he kept when he shouted, "Yes, I quit!" after being in Flair's figure four leglock. Flair then kicked Sting out of the Horsemen upon his challenge for the NWA Championship, resulting in a revived feud between the two which had to be delayed due to Sting injuring his knee, forcing WCW to slot Lex Luger as Flair's main challenger until Sting returned. On July 7, 1990, Flair dropped the title to Sting at The Great American Bash. After being unmasked as the Black Scorpion at Starrcade in 1990, Flair regained the title from Sting on January 11, 1991, in front of a near empty house due to the blizzard conditions in the New York City area. Prior to this reign, WCW split their recognition of a World Heavyweight Champion from the NWA, and Flair was subsequently recognized as the first WCW World Heavyweight Champion, while still being recognized as NWA World Champion. At the Clash of the Champions XIV: Dixie Dynamite on January 30, he wrestled Scott Steiner to a draw. On March 21, 1991, Tatsumi Fujinami defeated Flair in a controversial match in Tokyo at the WCW/New Japan Supershow. While the NWA recognized Fujinami as their new champion, WCW did not because Fujinami had backdropped Flair over the top rope in a violation of WCW rules. On May 19, 1991, Flair defeated Fujinami at SuperBrawl in St. Petersburg, Florida to reclaim the NWA title and retain the WCW Title. In doing so, he became an nine time NWA World Heavyweight Champion, breaking Harley Race's record of eight reigns. On June 14, at the Clash of the Champions XV: Knocksville USA, he defeated Bobby Eaton in a two out of three falls match.

In the spring of 1991, Flair had a contract dispute with WCW president Jim Herd, who wanted him to take a substantial pay cut. Herd had removed Flair as head booker in February 1990 and wanted to reduce Flair's role in the promotion even further, despite the fact that Flair was still a top draw. According to Flair, Herd also proposed changes in his appearance (i.e. by shaving his hair, wearing a diamond earring and going by the name "Spartacus") as well as his in-ring name in order to "change with the times". Flair disagreed with the proposals, and two weeks before the The Great American Bash, Herd fired him and vacated the WCW Championship. While Flair had left for the WWF he was still recognized as the NWA World Champion until September 8, when the title was officially vacated.

Flair signed with the World Wrestling Federation (WWF) in August 1991 and began appearing on television as one of the most hated heels the next month. Initially, he appeared on WWF shows with the "Big Gold Belt," calling himself "The Real World Heavyweight Champion." WCW sued Flair in an attempt to reclaim the belt, but Flair claimed that he owned the belt in lieu of the $25,000 deposit paid by NWA champions upon winning the title, which had not been returned to him when he was fired from WCW. The matter was settled later that year, with Flair's deposit being returned to him along with interest. Led by his "financial advisor" Bobby Heenan and his "executive consultant" Mr. Perfect, Flair repeatedly issued challenges to WWF wrestlers like Roddy Piper and Hulk Hogan, wrestling a team led by Piper at Survivor Series in 1991 and helping The Undertaker defeat Hogan for the WWF Championship that same night.

At the Royal Rumble in 1992, he won the Rumble match to claim the vacant WWF Championship. Flair drew number three in the Rumble match and lasted a then-record nearly 60 minutes, last eliminating Sid Justice with help from Hulk Hogan, who had been eliminated by Justice seconds earlier. In so doing, Flair joined Buddy Rogers as the only men to win the WWF and NWA World Championships in their careers.

After a planned program with Hogan was scrapped due to Hogan's hiatus following the WWF's steroid scandal, Randy Savage challenged Flair for the WWF title at WrestleMania VIII. In storyline, Flair taunted Savage by claiming that he had a prior relationship with Savage's wife, Elizabeth, and that he had the pictures to prove it (which were later revealed to be doctored photos). Savage defeated Flair for the title at WrestleMania. In July 1992, as Savage prepared to defend the title against The Ultimate Warrior at SummerSlam, Flair and Mr. Perfect sowed distrust between the two by suggesting that they would back one or the other during their match. They actually attacked both Savage and Warrior and injured Savage's knee, an injury that Flair exploited to regain the title in a match with Savage on September 1. His second reign was short-lived, however, as he lost the title to Bret Hart on October 12, 1992. Flair teamed with Razor Ramon to take on Savage and Perfect at the Survivor Series 1992. After losing a Loser Leaves the WWF match to Mr. Perfect on an episode of Monday Night Raw, Flair appeared in the Royal Rumble in 1993 (although the match with Perfect had been taped six days prior, it did not air until the following night) and then fulfilled his remaining house show commitments, making his last appearance on February 10, 1993, before returning to WCW. On The Ultimate Ric Flair Collection DVD, Flair described his first stint with the WWF as "the greatest year and a half of my career, outside the time I spent with Arn Anderson and The Four Horsemen."

Flair returned to WCW as a face in February 1993 and hosted a short-lived talk show in WCW called A Flair for the Gold. Arn Anderson usually appeared at the bar on the show's set, and Flair's maid, Fifi (portrayed by Wendy Barlow), cleaned or bore gifts. Once he returned to action, Flair briefly held the NWA World Heavyweight Championship for a tenth time after defeating Barry Windham at Beach Blast before WCW finally left the NWA in September 1993. At Starrcade in 1993, Flair was placed in a match, which was billed that if Flair lost, he would retire from wrestling. The match ended with Flair using a chop block and roll-up on the gigantic Vader to win the title for the second time.

In June 1994, Flair defeated Sting in a unification match, merging the WCW International World Heavyweight Championship with the WCW World Championship. This concluded a slow heel turn for Flair that started when he defeated Ricky Steamboat in a controversial manner some months earlier. Flair later feuded with Hulk Hogan upon Hogan's arrival in WCW in June 1994, losing the WCW World Championship to him in July at Bash at the Beach. Flair lost a retirement match to Hogan at Halloween Havoc and took a few months off before returning as a wrestler and part-time manager in 1995 (explained on-air by having Flair nag Hogan for months until Hogan agreed to let Flair come back). He and Randy Savage renewed hostilities when Savage arrived in WCW late in 1994, and their feud continued off-and-on for almost two years with each wrestler winning the WCW World Championship from each other at different times. Flair defeated Savage in a steel cage at SuperBrawl VI to win the WCW World title, which saw Savage betrayed by Elizabeth in favor of Flair. The Nature Boy also defeated Konnan on July 7 at Bash at the Beach to win the United States Championship. He vacated it in November of that year due to an arm injury.

Flair played a major role in the New World Order storyline in late 1996 and throughout 1997. He and the Horsemen often took the lead in the war against Scott Hall, Kevin Nash, and Hulk Hogan. Flair feuded with Roddy Piper, Syxx, and his old nemesis, Curt Hennig, in 1997 after Hennig was offered a spot in the Four Horsemen only to turn on Flair and the Horsemen at Fall Brawl in 1997. Hennig punctuated the act by slamming the cage door onto Flair's head.

He made a surprise return on September 14, 1998 to ceremoniously reform the Four Horsemen (along with Steve McMichael, Dean Malenko, and Chris Benoit). Flair feuded with Bischoff for several months afterward and eventually turned heel in the process. This culminating in a First Blood cage match at Uncensored against Hulk Hogan where both Bischoff's presidency and Hogan's WCW World Heavyweight Championship were on the line. Despite being the first to bleed, Flair won the match by submission thanks to biased referee Charles Robinson, who counted Hogan out. Robinson would be nicknamed "Lil' Naitch," idolizing Flair and officiating all of Flair's matches in his favor. As on-air "president," Flair began abusing his power much like Bischoff had, favoring villains over fan favorites and even awarding the WCW United States Heavyweight Championship to his son David and resorting to whatever means necessary to keep David U.S. Champion. Flair eventually formed a stable of followers which included Roddy Piper, Arn Anderson, and the Jersey Triad to keep things in order. Flair's reign as president came to an end on the July 19 episode of Nitro, facing Sting for the WCW presidency. During the course of the match, Sting had Flair in his Scorpion Death Lock, but with the referee knocked unconscious, no decision could be reached. A returning Eric Bischoff came to the ring and began ordering the timekeeper to ring the bell, which he eventually did, awarding the match and the presidency to Sting (who promptly gave it up upon receiving it).

Flair won the WCW World Championship twice during 2000, the company's last full year of operation. When WCW was purchased by the WWF in March 2001, Flair was the leader of the villainous group called the Magnificent Seven. During the final episode of Nitro on March 26, 2001, he gave an emotional speech regarding the company's greatness. Later in the night, Flair lost the final match in Nitro history to Sting. Nevertheless, Flair has repeatedly stated in various interviews how happy he was when WCW finally closed down; although, at the same time, the fact that many people would lose their jobs saddened him.

After a hiatus from professional wrestling, Flair returned to the WWF in November 2001 as the on-camera co-owner of the company.[16] Flair reappeared on Raw following the end of the "WCW/ECW Invasion" that culminated in a "Winner Take All" match at Survivor Series won by the WWF.[17] Flair's new on-screen role was that of the co-owner of the WWF, with the explanation that Shane and Stephanie McMahon had sold him their stock in the company to a consortium (namely Flair) prior to purchasing World Championship Wrestling and Extreme Championship Wrestling.[18] Flair's feud with Vince McMahon led them to a match at the Royal Rumble in 2002 in a Street Fight, where Flair defeated McMahon.[17] Flair also wrestled The Undertaker at WrestleMania X8 in 2002 where Flair lost after a hard fought battle and interference by Arn Anderson.[19] From then, the "co-owner" angle culminated in early 2002, when McMahon controlled SmackDown!, and Flair controlled Raw.[20] After Steve Austin abruptly left WWE while in a program with Flair, a match was hotshotted between Flair and Vince for sole ownership of WWE, which McMahon won, thanks to interference by Brock Lesnar.[21]Flair later became a villain by joining Triple H's "Evolution" stable.[22] Flair won the World Tag Team Championship with Batista twice in 2003 and 2004.[23][24] After Triple H took time off after Vengeance and for the rest of the summer, Flair would become a fan favorite again by beginning a short feud with Kurt Angle. Later, at Unforgiven in 2005, Flair defeated Carlito for the Intercontinental Championship.[25] He defended the title in a feud with Triple H before losing it to Shelton Benjamin.[26] Flair then took some time off in mid-2006 to rest and marry for the third time; he returned in June to work a program with real-life rivalry Mick Foley that played off their legitimate past animosity.[27] Flair defeated Foley at SummerSlam in an "I Quit" match.[28]

Subsequently, he was involved in a rivalry with the Spirit Squad on Raw. On November 5, 2006 at Cyber Sunday, he captured the World Tag Team Championship from the Squad with Roddy Piper. On the November 13 edition of Raw, Flair and Piper lost the Tag Titles to Rated-RKO, due to a disc problem with Piper and had to be flown immediately back to the USA as soon as Raw was off the air. On November 26, 2006 at Survivor Series, Flair was the sole survivor of a match that featured himself, Ron Simmons (replacing an injured Piper), Dusty Rhodes and Sgt. Slaughter versus the Spirit Squad. Flair then left television due to his divorce hearings. On the December 11, 2006 edition of Raw, Flair returned to team up with DX again. They defeated Rated-RKO and Kenny Dykstra.

Flair then began teaming with Carlito after Flair said that Carlito had no heart. Flair defeated Carlito in a match after which Carlito realized that Flair was right. Flair and Carlito faced off against Lance Cade and Trevor Murdoch in a number one contender's match for the World Tag Team Championship but were defeated. After weeks of conflict between Flair and Carlito, the team split up when Carlito attacked Flair during a match. At Judgment Day, Flair defeated Carlito with the figure four leglock. His career was put at risk following a match with Randy Orton on June 4, 2007.

On the June 11 edition of Raw, Flair was drafted from Raw to SmackDown! as part of the 2007 WWE Draft. He briefly feuded against Montel Vontavious Porter and rejoined forces with Batista to feud with The Great Khali; the alliance was short-lived, however, as Flair was "injured" during a match with Khali.

After a three month absence, Flair returned to WWE programming on the November 26 edition of Raw to announce that he would "never retire". Vince McMahon retaliated by announcing that the next match Flair lost would result in a forced retirement. Later in the night, Flair defeated Orton after a distraction by Chris Jericho. It was revealed on the 15th anniversary of Raw that the win or retire ultimatum only applied in singles matches. Flair won several "career threatening" matches against the opponents such as Triple H, Umaga, William Regal, Mr. Kennedy, and Vince McMahon himself among others. On March 29, 2008, Flair was inducted into the WWE Hall of Fame as a part of the Class of 2008 by Triple H. Flair became the first active wrestler to be inducted into the Hall Of Fame. The day after, Flair wrestled at WrestleMania XXIV in Orlando, Florida, losing to Shawn Michaels. This match was voted the 2008 PWI Match of the Year. Flair's fight to keep his career going garnered him the 2008 PWI Most Inspirational Wrestler of the Year award.

On the March 31, 2008 edition of Raw, Flair delivered his farewell address. Afterward, Triple H brought out many current and retired superstars to thank Flair for all he has done, including Shawn Michaels, some of the Four Horsemen and Chris Jericho, followed by The Undertaker and then Vince McMahon. Along with the wrestlers, the fans gave Ric a standing ovation. This event represented a rare moment in WWE as both the heels and the faces broke character and came out to the ring together. The Undertaker's and McMahon's entrances, however, were not shown on the TV taping of Raw for the week in order to preserve their characters, more in the case of the Undertaker as it involved him hugging Ric Flair and then raising his arm in victory, but were included in Nature Boy Ric Flair: The Definitive Collection DVD as extras.

Flair made his first post-retirement appearance on the June 16, 2008 edition of Raw to confront Chris Jericho about his actions from the previous week, when Jericho brutalized Shawn Michaels. Flair did not want to come out of retirement and have an official match, but challenged Jericho to a fight in the parking lot, until he was ejected from the building by Vince McMahon.

On the February 9, 2009 episode of Raw, Flair made an appearance to once again confront Chris Jericho, telling him to respect the WWE Legends and the fans. The segment ended with Flair punching Jericho. Exactly one month later, on the March 9, 2009 episode of Raw, Flair appeared during a Money in the Bank qualifier match between Jericho and Kofi Kingston, distracting Jericho which cost him the match. Flair distracted Jericho as revenge for Jericho's attacks on Roddy Piper, Jimmy Snuka and Ricky Steamboat. Jericho subsequently suggested Flair come out of retirement and challenged him to a match on the March 16, 2009 Raw.

That week, Flair declined Jericho's challenge to come out of retirement. Instead he, along with Ricky Steamboat, Roddy Piper and Jimmy Snuka attacked Jericho.[52] Flair made another appearance the next week, to accept Jericho's challenge on behalf of Steamboat, Piper and Snuka for a 3-on-1 handicap match at WrestleMania XXV. Jericho then proceeded to brutally attack Flair, causing him to bleed and even destroying the watch that was given to Flair from Michaels after Wrestlemania.[53]At the 2009 WWE Hall of Fame induction ceremony, Flair inducted Ricky Steamboat whom Flair called the hardest competition he ever fought. The next day at Wrestlemania XXV, Flair was in the corner of Piper, Snuka, and Steamboat for the match against Jericho. Jericho went on to win the match, and then went after Flair. While Flair was knocked down, Mickey Rourke came into the ring and nailed Jericho with an upper left hook, at which time Flair came in and held up Rourke's hand in victory.On May 17, 2009, Flair returned to WWE during the Judgment Day pay-per-view, coming to the aid of Batista, who was being attacked by The Legacy faction (Randy Orton, Cody Rhodes and Ted DiBiase). He also appeared the following night on Raw, in a verbal confrontation with Orton. He then went on to compete in a Backstage Brawl with Orton on the June 1st Edition of Raw, after an interference from the rest of The Legacy, the fight ended with Flair trapped inside a steel cage as he was punted by Orton.

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