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#1 Ric Flair
“To be the man, you have to beat the man” is not only one of the most iconic catchphrases of all-time; it still rings true today. More than 25 years following his famous interview at WrestleWar 1989 when he first uttered that phrase, Ric Flair is still the man. During the course of researching and compiling all of the information for this project, I moved a lot of people around on the list. Some guys were originally slotted much lower than they ended up being and some guys were slotted higher and went down. However, there was never really any debate that Flair was going to end up being number one; and despite some strong cases being made for other talent, Flair remains the top guy.
Flair holds onto the number one spot because he checks off the most boxes when it comes to evaluating a career. As a pure worker few have ever been better, both in the ability to exchange holds and work crisply and in the ability to sell his opponents offense and tell a story in the ring. Charisma-wise he was at times flamboyant and obnoxious, acting in a manner worthy of the nickname “The Nature Boy” which he adopted from Buddy Rogers, the mid-century star who popularized many of the classic heel traits associated with today’s villains. He could also play a sympathetic babyface, take a beating as well as anybody in wrestling history and get the audience behind him.
As a draw Flair was strong, if not quite on the level of guys like Hogan and Austin. He never had the benefit of being the top guy in New York City, and most of his prime was spent anchoring promotions from an older business model. Flair was a big wrestling star in the Mid-Atlantic and Southeast and was certainly better known in those parts than Hogan was in New York, but because the WWF was working in the media capital of the world and under the supervision of Vince McMahon, Hogan’s business numbers and ultimately his popularity would dwarf Flair’s. Still, Flair was probably the most popular non-WWF wrestler in the United States and Canada for about 15 years, and was a reliable draw wherever he went, even if that was often in smaller markets.
Flair came from humble beginnings, born an orphan in Memphis before being adopted by a couple and eventually moving to Minnesota. As a teenager Flair excelled in football and amateur wrestling, winning two state championships in wrestling in 1966 and 1968. He played football at the University of Minnesota upon graduating from high school, where he was a teammate of Greg Gagne, the son of American Wrestling Association owner and perennial champion, Verne Gagne. Flair eventually dropped out of school and was working at a night club when he encountered Ken Patera, an Olympic weightlifter who told Flair he was going to train with Verne Gagne to become a professional wrestler. Interested, Patera introduced Flair to Gagne and impressed by his amateur background, Gagne agreed to train Flair along with Patera.
After training with Gagne and British wrestling star Billy Robinson, Flair debuted in December of 1972, wrestling George Gadaski to a 10-minute draw. He used the ring name Ric Flair, which was remarkably close to his legal name of Richard Fliehr. In the early days of his career Flair hardly resembled the icon he would become. The former lineman weighed well over 250lbs and had a thick, muscled physique and dark brown hair. However, he still exhibited a lot of natural charisma in the ring and he quickly got the attention of different promoters who saw that Flair had something special.
After spending time mainly as a show-opening wrestler for the AWA, Flair would move onto the territory that he would become synonymous with, Jim Crocket Promotions and Mid-Atlantic Championship Wrestling. Shortly after his debut in May of 1974 he began teaming with Rip Hawk and in July they defeated Bob Bruggers and Paul Jones for the NWA Mid-Atlantic Tag Team Championships. They would hold the championships until December when Hawk got injured and had to be replaced by Brute Bernard and Flair and Bernard lost the titles to Paul Jones and Tiger Conway Jr.
In February of 1975 Flair won his first singles championship when he defeated Paul Jones for the NWA Mid-Atlantic Television Championship. A bully heel, Flair would defend the championship against charismatic babyfaces like Wahoo McDaniel and Rufus R. Jones before losing it to Jones in August. In September of 1975 he stepped up and won the NWA Mid-Atlantic Heavyweight Championship from Wahoo McDaniel, perhaps the biggest regional championship in the National Wrestling Alliance.
Just as it seemed Flair was going to excel to the next level in wrestling and become a national star, he was snatched right out of the air. On October 4, 1975, Flair was a part of a serious plane crash in Wilmington, North Carolina. The crash killed the pilot and paralyzed the legendary heel Johnny Valentine; Flair broke his back in three different places and was famously told by doctors that he would never wrestle again. However, Flair recovered and returned to the ring in February of 1976, resuming his feud with McDaniel. The injury did play an unforeseen role in the development of Flair’s career. When he returned to the ring he had a thinner physique and wrestled a different style from his bruising, physical character to a slicker, more antagonistic technical wrestling style, mixing in classic underhanded tactics. The new Ric Flair would eventually generate enough attention from fans that the iconic Buddy Rogers came out of retirement in 1978 to wrestle Flair. Flair defeated Rogers and was allowed to use the nickname “The Nature Boy”, which he adopted from Rogers and would arguably usurp Rogers as the most fabulous heel in wrestling history.
Coming off of his back injury Flair would win the NWA Mid-Atlantic Heavyweight Championship back from McDaniel and continued his feud with the popular babyface. McDaniel and Flair wrestled all over the territory having violent and bloody matches that transfixed crowds in the Southeast. McDaniel would finally win the NWA Mid-Atlantic Heavyweight Championship from Flair in Steel Cage match in Greenville, SC in September of 1976, only for Flair to regain the title a month later in a Championship vs Hair match, but McDaniel won it back in December.
In July of 1977 Flair captured the NWA United States Heavyweight Championship, probably the second most important championship under the NWA banner, behind only the NWA World Heavyweight Championship, when he defeated Bobo Brazil for the title. Flair would defend the championship against Brazil, Rufus R. Jones and Steve Keirn, but his best opponent would be a young babyface new to the territory, Ricky Steamboat. If Flair was the classic dirty heel in the model of Rogers, Steamboat was the classic slick-wrestling babyface in the model of Lou Thesz. Together they had fast-paced, dramatic matches that were probably the best wrestling matches going on in the United States during the late-1970s. Steamboat would win the championship in October and the two would trade the championship back and forth throughout 1979 in a prelude of the epic feud they would have a decade later.
Flair would continue to trade the United States Championship with the likes of Jimmy Snuka, Greg Valentine and Roddy Piper. Proving that he had everything that it took to be a regional champion, the call came from up top for Flair to become the top guy in the NWA. In June of 1981 Dusty Rhodes defeated Harley Race for the NWA World Heavyweight Championship. Despite Rhodes’ overwhelming popularity; the NWA board was hesitant to book him as the long-term champion, mainly because they didn’t think Rhodes’ status as a sub-par worker and his flabby physique would make a good long-term kingpin for the NWA. With Race currently out of the picture, the onus fell on Flair to take the NWA World Heavyweight Championship from Rhodes. In September of 1981, Flair defeated Rhodes for his first world championship.
Flair’s first reign as NWA World Heavyweight Champion lasted officially 631 days, where Flair would establish himself as the most reliable performer in perhaps the entire world. Flair throughout the 1980s came across as a hybrid star who bridged the gap between two different generations of wrestlers. With both the World Wrestling Federation and the AWA dominating wrestling above the Mason-Dixon line, the NWA, particularly with Flair as champion, became mostly a regional promotion based in the Southeast. Southern wrestling is different from the flamboyance of New York City and the mat-based style of the Mid-West, it is much more traditional with classic babyfaces and classic heels and a heavy emphasis on Southern wrestlers, particularly as babyfaces. That is part of the reason Flair was always billed from Charlotte, NC, even though he is really from Minnesota.
But Flair also helped take the stagnant NWA into the modern era with his character and presentation. Flair cut epic promos throughout the 1980s, coining many different catchphrases and always coming across as a total superstar in his promos. While the WWF was heading towards global domination on the backs of Hulk Hogan and a litany of colorful characters, Flair remained the best of the rest with his consistently entertaining promos and great matches. Flair got over with the southern audience in a way that few have ever done, but he was also colorful enough that he could be marketed all over the world as the universal superstar, which made him the perfect person to hold the NWA World Heavyweight Championship.
Flair defended the championship across the globe, including dates in Japan against Jumbo Tsuruta. It would be in the Dominican Republic that Flair would face some controversy over the NWA World Heavyweight Championship, as he was originally slated to drop the championship to local hero Jack Veneno, and Veneno would then lose the championship back to Flair shortly thereafter at a show in the United States. This is similar to booking patterns that had been used in Japan with Giant Baba enjoying a pair of short reigns as NWA World Heavyweight Champion before dropping the title back to the original champion at the end of the tour. Veneno, knowing he would be dropping the title as soon as he stepped foot in the US, refused to defend the championship outside of the Dominican Republic. His reward was to be stripped of his championship and was never acknowledged by the NWA as the champion, wiping his name out from the history books and Flair remained the champion. In January of 1983 Flair did a quick title swap with Carlos Colon in Puerto Rico, but similar to Veneno’s title reign it was never recognized by the NWA.
Flair’s first title reign officially came to an end in June of 1983 when Race defeated him. During his title reign Flair–despite embodying everything that a classic heel would do–began to get some crowd support simply because of how talented he was. Eventually the NWA decided that Flair may actually be better as a babyface than a heel, and he became a babyface towards the end of his title reign, made clear by having him lose the championship to Race, a perennial heel. The title loss was only a minor setback for Flair, as it was setting up a title chase that would culminate at the first Starrcade, a special event heavily promoted by the NWA and Jim Crockett Promotions with Flair and Race in a Steel Cage match for the championship as the headliner.
There had been large events and super shows promoted for years before Starrcade, but Starrcade was one of the first shows to be presented not only as a big event but also one that would be screened in arenas via closed-circuit television around the Southeast. The annual spectacular would become the godfather to annual PPV events, most notably WrestleMania which would take place a year later. The first event, held at the Greensboro Coliseum was a tremendous success, not only selling out the arena but the traffic caused by fans trying to get to the arena and the various screening facilities caused a massive backup, effectively shutting down transportation in the city. With former champion Gene Kiniski as the special guest referee, Flair defeated Race in the main event for his second NWA World Heavyweight Championship.
Flair would swap the championship with Race during a tour of the Pacific, losing the title to Race at a show in Wellington, New Zealand only to win it back three days later in Singapore. Once again, these reigns were never officially recognized by the NWA and for all that most fans knew Flair had never lost the championship at all. Flair however would officially drop the championship in May of 1984 to Kerry Von Erich. Von Erich won the title in front of a massive crowd of over 32,000 people at Texas Stadium in the first Von Erich Memorial Parade of Champions show, a memorial show for Kerry’s older brother David, who had passed away in February. The feel good story would come to an end just 18 days later as Flair defeated Von Erich to regain the championship at a show for All-Japan Pro Wrestling.
After defeating Von Erich, Flair would enjoy his longest championship reign, just under 800 days. Now back as a full-blown heel, Flair would defend the championship against the likes of Tully Blanchard, Wahoo McDaniel, Ron Garvin, Race and Genichiro Tenryu. He also defeated Rhodes in a match at Starrcade 1984. Being the NWA World Heavyweight Champion required touring the world and taking on all-comers, often times being the top babyface in the regional promotion that he was defending in. Naturally, that made it quite difficult for a long-reigning NWA Champion to be a babyface, because they were always coming into the babyfaces home territory and defending the title as the outsider. As charismatic as Flair was, it was hard for him to remain a babyface during this phase of his career.
In the spring of 1985, a new development in Flair’s career took place, one that would take his notoriety to even greater heights. Back in the 1970s, Flair was originally brought into the Mid-Atlantic territory as the storyline cousin of Gene and Ole Anderson, collectively known as the Minnesota Wrecking Crew. This storyline had been largely forgotten over the years, but would resurface when Ole Anderson and his new storyline cousin, Arn Anderson, began assisting Flair in his matches. They also began endorsing Tully Blanchard, a new wrestler from Texas, and took on James J. Dillon as their manager. Their first major angle came when they collectively beat down Dusty Rhodes in September of 1985, breaking his ankle. After the beatdown the group was collectively giving a promo when Arn Anderson compared the grouping to the Four Horsemen of the Apocalypse, a biblical reference to a group of cavalrymen who signaled the end of the world. The Four Horsemen, or just The Horsemen, would dominate Jim Crockett Promotions and therefore the NWA for the remainder of the decade.
As the star of The Horsemen, Flair became the indomitable champion. The storyline became that The Horsemen made it nearly impossible to get a fair fight with Flair, as they either interfered in matches or collectively beat down potential challengers. Over time the idea of a faction constantly interfering in matches and destroying the babyfaces would become a tired concept, but during the mid to late 1980s The Horsemen were a revolutionary concept, and every other faction that followed them were really just imitating The Horsemen. Even with The Horsemen by his side and regularly supporting him in matches, Flair still had a reputation for being a terrific competitor and cagey grappler. That meant that even if a wrestler was able to corner Flair and overcome The Horsemen, they still had to deal with one of the best wrestlers in the world in the ring, making it all but impossible to dethrone Flair.
During the same time the WWF had begun prospering as a national promotion and sensing an impending promotional war, the NWA looked to Flair and the Mid-Atlantic Territory to lead them. The idea of the NWA as an international promotion of separate organized territories began to fade in favor of the Mid-Atlantic promotion becoming the only real NWA promotion that mattered. Consolidating with other smaller promotions in the Southeast and owning a national television contract with Turner Broadcasting, the NWA had all the resources to go toe-to-toe with Vince McMahon and the WWF. Flair would prove to be the face of the war against the WWF, not only because he was the perennial champion but also because he was the antithesis of the WWF and its face, Hulk Hogan. Hogan was insanely popular, but for hardcore fans Hogan left a lot to be desired because his promos were repetitive and his matches poor. Flair on the other hand cut terrific, original promos and consistently had some of the best main-event matches in the world. Flair may have never reached the lofty heights of mainstream popularity that Hogan did in the 1980s, but he did supply an important alternative to the WWF for fans of more traditional wrestling.
In July of 1986, Flair’s title reign would be ended by Rhodes, who returned from his broken ankle and was out for revenge against Flair and The Horsemen. The build-up, which saw some of the best promos of both men’s careers given was red-hot and Rhodes peaked as a babyface during this feud against Flair, winning the NWA World Heavyweight Championship at The Great American Bash in Greensboro. Despite the tremendous build and the fulfillment of Rhodes winning the title, Flair would reclaim the championship just two weeks later and hold it for more than a year before swapping it with Ronnie Garvin, dropping the title to Garvin in September of 1987 and winning it back in November.
In November of 1988, Jim Crockett Promotions and the NWA were in financial peril. While Flair had remained a strong draw as champion, the company had been grossly mismanaged from a financial standpoint, overpaying talent and running up huge travel expenses. In one of the most important dealings in wrestling history, Jim Crockett Promotions were purchased by media-mogul Ted Turner and rebranded as World Championship Wrestling. With the financial support of Turner, WCW would be able to continue the war with the WWF throughout the 1990s and into the new millennium.
Flair would begin to feud with a young wrestler named Sting, a charismatic face-painted babyface who was beginning to catch on in the territory. At the first ever Clash of the Champions, a series of TV specials that aired on TBS, often utilized as free alternative to WWF PPV events, Flair wrestled Sting to a 45-minute draw in which Sting dominated Flair. Although Flair retained his championship, Sting’s dominance was strongly stated and he immediately became a top star in the company. The match became a prime example of Flair putting over other wrestlers and allowing new stars to be made at the expense of his reputation, a selfless act that helped create numerous stars throughout his career.
In the beginning of 1989, Ricky Steamboat was brought back from the WWF to feud with Flair. Fans remembered the tremendous matches Steamboat and Flair had a decade earlier over the United States Championship and since then both Steamboat and Flair had become much bigger stars. Steamboat had long been one of the top babyfaces in wrestling, but he hadn’t gotten to be a world champion, unlike Flair who had owned the NWA World Heavyweight Championship for the last decade. Steamboat would win the title from Flair in their first match, at the PPV event Chi-Town Rumble in February in a classic match that received a perfect five star rating from The Wrestling Observer. It was the first of an epic trilogy of matches between the two, all three of which were critically acclaimed as instant classics. Steamboat beat Flair under controversial circumstances at a Clash of the Champions event in April in a 55-minute marathon; but Flair would win the final match between the two at WrestleWar, regaining the title.
His next opponent would be Terry Funk, a former NWA World Heavyweight Champion from the 1970s who had come back to the United States as a wild heel whose unpredictable behavior struck fear in wrestlers throughout WCW. He joined forces with Gary Hart to form the J-Tex Corporation and teamed up with The Great Muta, Buzz Sawyer and The Dragonmaster to attack Flair. This began to turn Flair babyface and his turn would be made official when he re-formed The Four Horsemen with Sting replacing Tully Blanchard. Together The Horsemen were able to get the better of the J-Tex Corporation, culminating in a successful title defense against Funk in a classic “I Quit” match in November of 1989. The face turn would be short-lived however, as he then feuded with Sting over the NWA World Heavyweight Championship, kicking Sting out of The Horsemen and eventually dropping the title to him in July of 1990.
Flair would chase Sting all the way to Starrcade 1990, where he was involved in a convoluted storyline as a masked character known as The Black Scorpion. The Black Scorpion’s identity was never revealed leading up to Starrcade, and the only information given was that he was from Sting’s past. It ended up being Flair, the most predictable result possible, and Sting defeated Flair in Steel Cage match at Starrcade to retain the championship. However, Flair would win the title back two weeks later at a house show.
In the summer of 1991 Flair began to get in a contract dispute with WCW management and Jim Herd, who was in charge of the company at the time. Herd, whose inexperience in pro wrestling would soon become painfully evident, thought the 42-year old Flair was too old to represent WCW and wanted Flair to take a pay cut and reduce his role in the company. Flair obviously disagreed and a game of chicken took place between the company and its largest star that eventually saw Flair stripped of the world title and in September, he signed with the WWF. This proved to be catastrophic for WCW for two reasons; first Herd grossly underestimated how important Flair was to the company, as in his absence fans loudly chanted for Flair long after he had left the company, poisoning the company’s attempts to replace Flair. In addition, Flair had originally put a deposit down on the NWA World Heavyweight Championship meaning that he literally owned the championship belt, so even though he was stripped of the title and no longer recognized, he still had the title belt, and was free to bring it anywhere he wanted, including the WWF. A legal battle ensued that eventually led to the WWF being unable to show the title on television and eventually led to it being returned to WCW.
The WWF signing Flair was quite the coup; since Flair had been the face of the opposition for years and WWF fans had always dreamed of a match-up between Flair and Hogan as a clash between the two biggest icons of the 1980s. However, the match would never end up taking place for a variety of reasons, some say that Hogan did not want to lose to Flair and vice-versa, that the house show matches they worked underperformed, etc. Flair and Hogan would never meet on the big stage during Flair’s first run in the WWF, and that would hurt the memory many fans have of Flair’s WWF tenure; but although Flair never did have that match with Hogan, he certainly had a big impact in the WWF.
After debuting in September he formed a team to defeat Roddy Piper’s team in a 10-man Elimination Tag Team match at Survivor Series and later cost Hogan the WWF World Heavyweight Championship in a match against The Undertaker. After Flair interfered in subsequent rematches, the title was vacated and was to be rewarded to the winner of the 1992 Royal Rumble. In a vintage Flair performance, he entered at number three and lasted nearly an hour to win his first WWF World Heavyweight Championship. He would lose the championship to Randy Savage in the main event of WrestleMania VIII, but regained it in September when Flair and “Mr. Perfect” Curt Hennig injured Savage’s knee prior to the match, allowing Flair to use the Figure-Four Leglock (another import from Buddy Rogers) to win his second WWF Championship.
Despite this success, Flair never quite fit in with the WWF. He lacked the political capital he had in WCW, not to mention at this point in his career as an aging legend he would be a beloved babyface in his home company and not a heel in a rival company. The style of matches in the WWF were different and while they were mostly good, they were not up to the lofty standards he had set for himself in WCW. Flair dropped the championship to Bret Hart in October of 1992 and told McMahon that he wanted out of the company. Vince McMahon and Flair agreed to a deal when Flair was originally signed that if Flair at any time wanted out of his contract McMahon would let him walk, and to his credit McMahon held true to his word and only asked Flair to lose on the way out to Hennig, which Flair did in a Loser Leaves WWF Match on an early-episode of Monday Night RAW in January of 1993.
Flair returned to WCW to great fanfare in February, but do to a no-compete clause in his contract he could not wrestle immediately and instead hosted a talk-show on WCW television. He finally returned to the ring in June of 1993 and instantaneously regained his spot at the top of the company by defeating Barry Windham for the NWA World Heavyweight Championship at Beach Blast in July. Now a beloved babyface, he successfully defended the title against Paul Orndorff, before losing the championship (renamed the WCW International World Heavyweight Title, merged later with the WCW Would Heavyweight Title) to Rick Rude in September.
Eventually Big Van Vader won the WCW World Heavyweight Title and was set to defend it against Sid Vicious at Starrcade 1993, but Vicious was fired from the company because of an October fight with Arn Anderson which involved Vicious stabbing Anderson with a pair of scissors. To save the main event, Flair was called in and put his career on the line for a title match against Vader. Against all odds, Flair rolled-up Vader to win his 11th world title. The match with Vader at Starrcade might be the most defining moment of Flair’s career as it epitomized his true genius as a performer. Against Vader, a 400lb super-heavyweight with great agility, Flair was really in trouble. Vader was younger, bigger, stronger, meaner and even faster than Flair. Flair only had guile and his veteran instincts, and yet despite Vader dominating the match, Flair was able to fox his way to a victory; which was met by a tremendous roar from the crowd who had grown to idolize his cleverness over the years.
Despite the fact that Flair was clearly the best babyface in the company, WCW decided to turn him heel again, having him wrestle old-rival Ricky Steamboat in a pair of championship matches in 1994. This would become a theme for Flair later in his career, as his ability and popularity was often undermined by WCW’s ridiculous booking strategies and outright stupidity. Hogan, fresh off his dispute with McMahon that led to him leaving the WWF, signed with WCW and was of course given a monster push. He faced Flair at the 1994 Bash at the Beach and defeated Flair for the world title in the matchup that WWF fans had been denied during Flair’s run in the company earlier that decade. Flair chased Hogan for the championship before losing a Steel Cage match at Halloween Havoc that forced Flair into a brief retirement due to a stipulation in the match.
After taking some time off, Flair wrestled at the WCW/New Japan Pro Wrestling Supershow in Pyongyang, North Korea that drew the all-time wrestling attendance record and saw Flair wrestle Antonio Inoki in the main event. Back in the US he returned to the ring and reformed The Four Horsemen in the fall of 1995, this time the stable included Arn Anderson, Brian Pillman and Chris Benoit. In December of 1995 he was able to defeat Randy Savage (part of a new wave of talent that followed Hogan to WCW) in the main event of Starrcade to win the WCW World Heavyweight Championship. Flair and Savage would do a title swap early in 1996 that saw exciting matches and strong storytelling by the two legends. The feud between Savage and Flair is notable for increasing house-show attendance throughout WCW and inching them closer in the war against the WWF, with WCW eventually usurping the WWF later that year with the introduction of the nWo.
After losing the championship to The Giant in April, Flair began a slow descent in WCW’s hierarchy as the nWo began to take over the company, both literally and figuratively. Although still very popular, Flair often took a backseat to other WCW stars both in the nWo and outside the faction. Over the next several years the booking of his character would become wildly inconsistent, making it nearly impossible for fans to follow. At the beginning the now-babyface Horsemen took the lead in the fight against the nWo, but their name value took a hit when Pillman left the company and he was replaced by Steve “Mongo” McMichael, a former NFL player whose minimal name value was offset by his horrific wrestling ability. Up until this point The Four Horsemen had been a protected group of wrestling elites, with the introduction of a complete novice in McMichael the group was taken less seriously. Failure to defeat the nWo in any meaningful match also hurt the group and eventually they were mostly reduced to mid-card fodder.
Flair then got in a real-life feud with booker Eric Bischoff after Flair no-showed an episode of Thunder (Flair insisted that he had given WCW plenty of notice that he was not going to be at the show) and a law-suit followed. After that was settled Flair returned to the company in September of 1998 and worked a feud with Bischoff, culminating in a match at Starrcade which Flair lost when Curt Hennig interfered and gave Bischoff a comically large set of brass-knuckles to hit Flair with. Flair would continue to feud with Bischoff, eventually winning control of WCW from him and becoming the storyline president of the company. He parlayed that into a championship match against Hogan, which he won for another world title victory in March of 1999.
The booking of Flair and indeed much of WCW would become so fractured throughout 1999 that it became unnecessary to even really document, because so much changed week-to-week that no sole match, incident or storyline truly had long-term effects. Flair turned heel once more, abusing his power as president of WCW to aid his son David, in his quest to remain eternal United States Champion. For some reason WCW matchmakers were obsessed with Flair’s family as they were constantly involved in storylines during the late-1990s. Scattered storylines included but were not limited to; Flair being sent to a mental asylum, Flair going crazy on Nitro and taking off his clothes and Flair being quite literally buried in the desert. A lot of people thought it was embarrassing for Flair to continue to wrestle as he neared 50 and was put in bizarre storyline after bizarre storyline, but what was really embarrassing was how poorly WCW used their most iconic star and someone who was still beloved by the fans regardless of how insane the company tried to make him look. He did have two final WCW World Heavyweight Championship reigns in 2000, but the title had been so devalued by constant changes that they meant very little.
After WCW mercifully closed down, Flair retired until returning to the WWF in 2001 when he emerged as a co-owner of the company along with McMahon. They feuded over control of the company leading to a Street Fight at the 2002 Royal Rumble which Flair won. After losing to The Undertaker at WrestleMania X8, Flair would lose control of the company to McMahon in a match that saw Brock Lesnar interfere and cost Flair the bout. He returned in September when he assisted Triple H in retaining the World Heavyweight Championship in a match against Rob Van Dam at Unforgiven. Flair began managing Triple H and also took Batista and Randy Orton under his wing as well, forming Evolution.
The cleverly designed Evolution stable was built around the idea that it was a consortium of the past (Flair) present (Triple H) and future (Batista and Orton) of professional wrestling. Despite being in his 50s Flair still wrestled for WWE and continued to have solid matches against the likes of Shawn Michaels and Chris Jericho. Batista and Flair won the World Tag Team Championships from the Dudley Boyz in December of 2003 and held them until February of 2004. At SummerSlam Orton defeated Chris Benoit for the World Heavyweight Championship, which caused a rift in Evolution that proved to be the beginning of the end, eventually leaving to the departures of Batista and Orton. After Batista defeated Triple H for the World Heavyweight Championship in May of 2005, the group was officially dissolved and Flair became a babyface and won the Intercontinental Championship.
Triple H returned from a hiatus in October of 2005 and turned on Flair, igniting a feud. Flair defeated Triple H with the Intercontinental Championship on the line in a bloody cage match at Taboo Tuesday in November of 2005 that harkened back to Flair’s glory days in the 1980s. Triple H would get the last laugh however, defeating Flair in a Last Man Standing match at Survivor Series later that month. Flair then became a contender for the WWE Championship, which was being held by Edge and led to a memorable Tables, Ladders and Chairs match on an episode of RAW in January of 2006, culminating in Flair taking a big bump off of a ladder and through a table. Flair continued to chug along in WWE, remaining a key cog in the mid-card and feuding with Mick Foley and Carlito.
After a hiatus Flair returned to RAW in November of 2007 when Vince McMahon announced that the next match Flair lost would be his final match, meaning he had to win every match he was in to keep wrestling. This eventually led to a match at WrestleMania XXIV against Shawn Michaels, which saw Michaels defeat Flair in a tremendous match that officially retired Flair.
Of course if you have been reading the list for this long you would know by now that people rarely stay retired, and Flair is no exception. In 2009 he wrestled Hogan for some shows in Australia and then found his way to TNA, wrestling a dozen matches for them in 2010 and 2011. While Flair has every right to keep wrestling, for a lot of fans Flair’s last few years as an active wrestler were uncomfortable, as Flair was nowhere near his wrestling prime and had some truly awkward matches. He hasn’t wrestled since losing to Sting in September of 2011, so it looks like it is safe to say he is actually retired for good.
Flair’s career is one of persistent excellence and determination. Despite a serious setback early in his career, Flair outworked the rest of the competition to become an iconic heel and later a beloved babyface. Not only was he driven to become a complete wrestler and a meticulous attention for putting together terrific matches, he was also naturally gifted with charisma that few in wrestling have ever been blessed with. In addition, he remained better longer than almost anyone else in wrestling history, still having good matches and cutting great promos well into his 50s. His staying power as a top name is nearly unmatched, and is coupled with his ability to consistently put new stars over and create rivals without losing any of his own prestige. Nobody has sustained such consistent greatness and been asked to do so much throughout their career and done it at a high level like Flair, and that is why he is still the man.
The Final Top 50:
49. Superstar Billy Graham
47. El hijo del Santo
45. Bruiser Brody
43. Kurt Angle
42. Hiroshi Tanahashi
41. The Sheik
39. Perro Aguayo
38. Ricky Steamboat
37. Toshiaki Kawada
36. Jushin Thunder Liger
35. El Canek
33. Jack Brisco
32. Shinya Hashimoto
31. Roddy Piper
30. Genichiro Tenryu
28. Abdullah the Butcher
27. Keiji Mutoh
26. Bob Backlund
25. Mil Mascaras
24. Nick Bockwinkel
22. Shawn Michaels
20. Riki Choshu
19. Dusty Rhodes
18. Dory Funk Jr.
16. Harley Race
15. Andre the Giant
14. Kenta Kobashi
13. The Rock
12. Jumbo Tsuruta
11. Stan Hansen
10. The Undertaker
9. Verne Gagne
8. Terry Funk
7. Mitsuharu Misawa
6. Giant Baba
5. Bruno Sammartino
4. Antonio Inoki
3. Hulk Hogan
2. Steve Austin
1. Ric Flair