Celebrating Ric Flair’s Best WWE Moments 28 Years After Debut

Erik Beaston@@ErikBeastonFeatured ColumnistSeptember 9, 2019

Celebrating Ric Flair’s Best WWE Moments 28 Years After Debut

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    Credit: WWE.com

    On September 9, 1991, Ric Flair debuted on WWE television, something few imagined would ever happen after a decade spent as the face of NWA and WCW.

    What ensued was just over a year of magical moments and matches that further cemented Flair's status as the greatest wrestler to ever lace a pair of boots. Though his stint with the company was short-lived, he returned in November 2001, embarking on seven more years of bliss with Vince McMahon's company.

    Now, 29 years later, celebrate the 10 most memorable moments of his WWE career, limited exclusively to those that unfolded in the promotion and featuring some of the most emotionally raw occurrences in company history.

Honorable Mention: The Debut

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    September 9, 1991 saw the unfathomable debut of Ric Flair in Vince McMahon's WWE on its Prime Time Wrestling program.

    The longtime face of the National Wrestling Alliance and Ted Turner's WCW, Flair arrived in company with the competition's heavyweight title, claiming to be the real world's champion.

    Joined by Bobby "The Brain" Heenan, Flair cut a promo addressing both "Rowdy" Roddy Piper and Hulk Hogan, making it clear that he was both a heel and targeting two of the biggest, most recognizable babyfaces on the roster.

    It was a brief moment in time that is not as memorable as the other moments on this countdown but it deserves mention nonetheless.

10. Tables, Ladders and Chairs

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    Credit: WWE.com

    The Nature Boy had been part of many memorable, classic matches by the time the January 16, 2006 episode of Raw rolled around, but he had never ventured into the realm of tables, ladders and chairs. That changed when he challenged Edge for the WWE Championship in a blockbuster main event.

    On that night, Flair proved that while he may not have been the performer he once was, he could still deliver a stellar performance by masking his limitations with weaponry and big bumps.

    The audience popped for Flair, believing the legend was moments away from claiming the top prize in WWE on more than one occasion. Unfortunately, he fell short of claiming the title but did manage to deliver one of the more pleasantly surprising TLC matches in the history of the popular gimmick bout.

9. Intercontinental Champion

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    Credit: WWE.com

    Flair had won just about every major title there was to claim by the time September of 2005 arrived, except for one. The intercontinental title, the coveted midcard title with a long history of preparing young stars for a high-profile push, had eluded Naitch. 

    That is, until the opening match of the Unforgiven pay-per-view, which saw Flair battle Carlito.

    Withstanding an onslaught by the arrogant, confident and cocky villain, Flair trapped the second-generation Superstar in the Figure Four and tapped him out. After the match, Flair celebrated the title win as only he could: with a bevy of beauties, some champagne and a handful of Viagra in the back of a limousine.

    Flair would hold the title into February of 2006 and along the way, helped develop young stars such as Shelton Benjamin, Chris Masters and even prepared Edge for his long-awaited main event run, proving he could be as valuable to wrestling in the new Millennium as he was at the height of his run as world's champion.


8. A Royal Rumble Street Fight

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    Credit: WWE.com

    The war between Flair and Vince McMahon over ownership of WWE came to a head at the 2002 Royal Rumble, where Naitch and the CEO battled in an emotionally charged Street Fight.

    McMahon had beaten, bloodied and humiliated Flair in the weeks leading into the match and did the same throughout the first half of the high-profile bout. Flair wore the proverbial crimson mask while his children watched from ringside. McMahon, the dastardly heel, taunted the Flair family, beating their father in front of them.

    Fueled by vengeance, Flair fought back into the match, pummeled McMahon and punished him with the Figure Four, which forced the tapout and earned him his first pay-per-view victory in WWE since the 1992 Royal Rumble match a decade earlier.

    The match, Flair's first great one of his latest WWE run, helped him rediscover his in-ring confidence and proved that even at age 52, he could still deliver show-stealing performances by relying on his ability to generate emotion from the audience.

7. The WrestleMania Co-Main Event

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    Credit: WWE.com

    For weeks leading into WrestleMania VIII, WWE champion Flair claimed to have compromising images of Miss Elizabeth, taunting "Macho Man" Randy Savage and vowing to expose those images for the world to see on wrestling's grandest stage.

    While those threats never came to fruition, an emotionally intense championship clash between Naitch and Savage did, stealing the show at The Granddaddy of Them All. Flair bled and bumped around ringside for his ferocious, vengeful opponent but still managed to control the pace of the bout by targeting Macho Man's injured knee.

    Unfortunately, not even the assistance of associate Mr. Perfect could preserve Flair's title reign as Savage fought fire with fire, rolling him up and holding the tights to win the red-hot match.

    Still, despite the loss, it was Flair's first truly great performance on the WrestleMania stage and his last for an entire decade.


6. Loser Leaves Town

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    Credit: WWE.com

    The relationship between Flair and Mr. Perfect disintegrated in fall of 1992, when Perfect came out of retirement to partner with Randy Savage against Flair and Razor Ramon at the Survivor Series pay-per-view.

    That chain of events sparked a rivalry between the two legendary in-ring competitors, culminating with a Loser Leaves Town match on the January 23, 1993 episode of Raw.

    For 20 minutes, the Hall of Famers clashed, each trying to drive their hated rival from the company. In the end, it would be Perfect who scored the win, sending Naitch packing back to Turner's WCW.

    The match was an instant classic, rightfully earning rave reviews and capping Flair's first stint with WWE in fitting fashion. More importantly, it provided the upstart Raw program with its first truly great match upon which to build momentum and become the flagship show of WWE.

5. A New Owner

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    Credit: WWE.com

    Just 24 hours after WWE vanquished the evil WCW/ECW Alliance in the main event of Survivor Series, the man most synonymous with Ted Turner's promotion walked that aisle once more as Flair emerged from the shadows to confront Vince McMahon and reveal himself the new co-owner of the company.

    Flair, it turned out, had purchased Shane and Stephanie McMahon's ownership stakes when they purchased WCW and ECW, respectively.

    The pop for The Nature Boy's return in his hometown of Charlotte on the November 19 episode of Raw remains as loud a reaction as any Superstar has ever received. The magical moment gave way to months of back-and-forth between Flair and McMahon and led to some questioning why the 16-time world champion had not been brought in earlier to help boost the significance of the Invasion storyline.

    Despite the timing, Flair's return sparked a seven-year run that would be responsible for more unforgettable moments and cementing his legacy as one of the most enduring personalities the industry had ever produced.

4. The Battle of the Icons

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    The two most iconic stars in wrestling history, Flair and Hulk Hogan had never found themselves in the same promotion at the same time, robbing fans of a genuine dream match. Flair, synonymous with the NWA, and Hogan with WWE, had guided the industry to unprecedented heights and left fans wondering who would win if they ever clashed.

    When Flair joined McMahon's company in September 1991, the possibility of a showdown with Hogan became reality.

    On October 25, 1991 in Oakland, the much-anticipated dream match finally occurred. The bout headlined an untelevised live event, a test-run for a bigger, more significant match between the Superstars later down the line.

    The result was inconsequential (Hogan won via referee decision) because no one would see it outside of the fans in that arena on that night. What mattered was that Flair and Hogan finally squared off in a match a decade in the making.

    A string of rematches, including bouts in Hershey, Pennsylvania and New York's famed Madison Square Garden, featured largely the same results. Unfortunately, weaker-than-expected houses essentially canceled plans for the duo to headline WrestleMania and left fans wondering what might have been had they clashed on wrestling's grandest stage.

3. Celebrating Naitch

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    The May 19, 2003 episode of WWE Raw saw Steve Austin force Triple H to defend his world heavyweight title against an opponent of his choosing. The only catch? It had to be a former world champion. The Game, sensing he could defeat his associate relatively easily, chose Flair to defend against in the night's main event.

    Naitch, though, had no plans to lay down for The Cerebral Assassin and let him diminish his legacy. 

    Live from Greenville, South Carolina, home of some of his greatest triumphs, Flair channeled the gutsy performer who had amassed 16 heavyweight titles and nearly defeated Triple H. For just over seven minutes, the iconic competitor captivated audiences, coming within seconds of wrestling the title away from his protege.

    In the end, the champion flattened Flair with the Pedigree to win the match and retain the title. The performance was, arguably, Flair's finest since returning to WWE in November 2001 but was not the end of his night.

    After the Spike TV broadcast concluded, Superstars from the locker room poured into the arena in celebration of Flair. They paid homage and showed respect for the most influential star in wrestling, celebrating him in front of an audience that had been there for some of his greatest wars.

    Flair cried, his legacy endured and fans had another magical moment from Naitch that eventually made its way out to the masses.

2. Leave the Memories Alone

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    Credit: WWE.com

    By 2008, it was time for Flair's career to wind down and the evil Mr. McMahon necessitated it, announcing that Flair's next loss in a WWE ring would be his last. Surviving challenges from MVP and Mr. Kennedy, Flair took exception to a Hall of Fame induction and friend Shawn Michaels' celebration of his career. Not one to be pitied, he challenged HBK to a match at WrestleMania XXIV.

    That match would turn out to be one of the most genuinely emotional bouts in the long and illustrious history of that event.

    Flair turned back the clock, delivering one last great performance as he went toe-to-toe, move-for-move with the standard-bearer in sports entertainment. Despite a focused attack, he still fell prey to Sweet Chin Music. Showing the gutsiness that defined his career, he stood up one last time, tears in his eyes, and watched as Michaels delivered the unforgettable "I'm sorry, I love you" line.

    Another Sweet Chin Music and three seconds later and the career of wrestling's greatest had come to an end.

    The match, the story surrounding it and the ceremony from the following night's episode of Raw all served as a celebration of all things Flair. It was emotional, heartbreaking and real. It was a reminder of the emotions Flair generated and proof of his unwavering ability to make people care.

    The long walk up the ramp and to the back remains one of the more iconic moments in WrestleMania history.

1. "With a Tear in My Eye..."

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    "With a tear in my eye, this is the greatest moment of my life," Flair said moments after winning the WWE Championship in the 1992 Royal Rumble match.

    His hour-long performance in that match and the championship victory capped off an unlikely journey to Vince McMahon's company after a contentious falling out with WCW. For Flair, the win represented McMahon's trust in him to be the top dog in the promotion and evidence of his ability to succeed in the biggest company in the industry.

    The tears were real, the emotion was legitimate. 

    After being devalued and denounced by WCW management for the last two years, he had stuck it to president Jim Herd, proving he did not need that company's 15 pounds of gold because he was more than capable of going elsewhere and winning more.

    The engaging post-match promo was somehow even better than Flair's five-star performance in the Rumble match itself and igniting what would prove to be a one-year run with the company that was equal parts acclaimed and refreshing for Flair, personally, as he has revealed numerous times since the monumental moment that January.