“The Nature Boy” Ric Flair is often cited as being one of last (and possibly most successful) NWA main event draws. His career, spanning over 40 years, has produced some of the most important matches, influential promos, and ground breaking stables in wrestling history. Flair’s name has been synonyms with success.
While Hulk Hogan may always be the greatest wrestling superstar of the 1980’s there is no doubt that Flair was it’s greatest and prolific wrestler. Period.
Credited as either a 16 or 21 time World Champion, Ric Flair stands second to no one when it comes to “being the man.”
However, accomplishments aside, Ric Flair has put on some of the most textbook smart wrestling matches ever. While these contests are absent of the modern flashy moves we have all become custom to they are without question some of the most powerful wrestling matches ever caught on tape.
Regardless of whether he was 28 or 58 Ric Flair knew how to entertain and, more importantly, tell a story.
I won’t remember Flair for his insane antics, but for his being probably the best storyteller in professional wrestling history. Today, we look at Flair’s greatest stories given to us through his blood, sweat, tears, and perseverance to be “the man.”
RIC FLAIR VS. SHAWN MICHAELS (WRESTLEMANIA XXIV)
For pure emotion alone this match deserves recognition.
I think this match with Shawn is a fitting tribute to the active career of a man who wrestled for many decades.
Both men had strong motives and difficult decisions to make. Flair’s determination to prove that he was still the great wrestler he once was forced him into picking someone he considered to be one of the greatest of all time to wrestle at WrestleMania. Shawn’s difficult dilemma of having to possibly “pull the trigger” and end the career of a man he loves and respects.
These elements provided a deeper layer of story and context to the match gave the ring work great purpose.
It isn’t even close to either man’s greatest technical marvel and I will say that this match would not have even grabbed the honorable mention spot without these story elements that really made this match ten times better than it actually was.
Being Flair’s “last match” (in the WWE at least) also helped it claim the honorable mention spot over several other worthy matches from his second run with McMahon’s promotion.
This match is more raw emotion than ring action, but it without a doubt achieved it’s goal of evoking a response from the viewer. I think, even if it is not longer his final match, that this will be his final match worth talking about. The spiritual end of his storied career. I suppose that makes it important enough, still.
10. RIC FLAIR VS. HULK HOGAN (BASH AT THE BEACH 1994)
I will not lie to you and say that this was a technical marvel, but it was just good enough to skate into the final position. Where this match really wins the viewer over is the entertainment aspect of that match. This was the two biggest stars of the 1980s finally going at it in one of the biggest money matches in professional wrestling history.
While Flair may have been one of the most beloved and respected men in professional wrestling in the early 1990s, at his pinnacle of popularity, Hulk Hogan was bigger than all of professional wrestling. He transcended pop culture.
This match, like many matches in WCW, would be done to death. Once a dream match, these two have had more rematches than I would care to recap. They had matches in WCW, WWE, TNA for over three decades. It actually became embarrassing, but at Bash at the Beach 1994 it was still special.
I sort of felt bad for Flair as I watched this match as Hulk Hogan, who was having his first ever match for WCW, won the belt off of the man who helped carry WCW (Jim Crockett Promotions) for almost a decade at that point.
Then he just got pushed aside. It’s terrible really, but Flair made Hulk Hogan look so much better than he actually was. Hogan could pop the crowd for sure, but Flair made this match worth a damn from an in-ring perspective.
9. RIC FLAIR VS. TRIPLE H (TABOO TUESDAY 2005)
I tried very hard to avoid putting any matches from Flair’s second run into the Pro Wrestling Countdown as I felt it would have been disrespectful to all of the wonderful matches he had in his prime. However, I have a huge respect for the program he did with “The Game” Triple H in 2005.
It was the last match I added to this Countdown, but I feel like you will all see where I am coming from in giving it this position. I originally was going to have his match with Shawn Michaels represent his entire second run, but after viewing his work with Triple H in 2005 I had to renege my decision and add this contest.
This story was very much the old master taking on the young samurai. Triple H wanted to put Flair out of his misery so he could stop “embarrassing himself.” Triple H said that he was tarnishing the memory of his idol.
Triple H used Flair as a punching bag for much of the contest with Flair only getting in enough offense to defend himself.
Pro wrestling is a perfect playground for the Student/Teacher storyline. This was two master of pacing going at it. Triple H controlling the entire match with Flair only being able to fend him off was a perfect metaphor for the old guard standing the test of time.
Flair played the beaten down old master who may not have had the precision he used to, but the fire for competition still burned. Triple H was the youthful student putting down his old master. It was just perfect storytelling.
This was an old school style dissection from both guys on one other. While it might have been a tad slow for some, it was really engaging when they picked up the pace. The hot crowd at Taboo Tuesday didn’t hurt either.
Flair won here, but only by the skin of his teeth.
8. RIC FLAIR VS. MR. PERFECT (WWE RAW, JANUARY 1993)
Occurring on only the third ever edition of WWE Monday Night Raw, Curt Hennig and Ric Flair had what I would say was the first match worth watching in this shows now 20+ year history.
Incredibly all this time has passed and it still stands as one of the most noteworthy matches in the history of the weekly show, and one of my personal favorites. This was also a Loser Leaves Town match that was set up to give Flair a logical exit so he could return to WCW later that year.
This match was a result of Mr. Perfect having a falling out with Flair and Heenan months earlier after “The Brain” insinuated that he could no longer wrestle at the level he once did. This was marked the face turn of Mr. Perfect and his return to the ring following an extended leave following his match with Bret Hart at the 1991 SummerSlam.
Flair and Hennig had several matches together with the later ones occurring in WCW, but for me nothing topped their surprisingly good television match which occurred in an era where the idea of giving long and engaging matches away on free television was just beginning to come around.
I don’t know if Hennig played the babyface role to perfection here, but we do see Flair ham-up his heelish tactics. He used just about every clique move in the book behind the referee’s back to try to send Mr. Perfect packing and I think this helped sway the crowd to pop for Hennig.
My only complaint is with a few awkward spots that interrupted the flow and like most matches from this era there were a few slow moments, but that was just the style of the time. Outside of that this was a stellar display of entertainment and pacing.
Ric Flair would be back in WCW less than a month after this match. Hennig would spend very little time in the ring for the WWE after 1993 and also later jumped ship to WCW in 1997.
Probably one of Raw’s most forgotten classics. If you’ve never had the opportunity to catch it go do so. It was the quickest 20 minutes match I’ve ever watched.
7. RIC FLAIR VS. HARLEY RACE (STARRCADE 1983)
I’m starting to believe the cage matches will never be able to live up to the glory they once did.
I think the problem lies in the fact that it has seen so many variations that now make a traditional one-on-one cage match look like a relic from a bygone era. In saying that, matches like this contest between two legendary NWA performers, are what helped establish the gimmick as one of the most brutal of all time.
In 1983, WCW was still known as Jim Crockett Promotions and was still under the heavy guise of the National Wrestling Association. Naturally this match was for Race’s NWA Heavyweight Championship and occurred at the first ever Starrcade event which would go on to be WCW’s answer to WrestleMania.
This match I think does a great job of communicating what the NWA was all about. Traditional, old school, professional wrestlers. No glitz. No glamour. Just two men. Tough as nails. Entertaining the crowd with a fight.
Many current fans do not have a adequate appreciation for Harley Race’s accomplishments and his work, but he was absolutely vicious in this match with Flair.
He dropped countless knees right on the challenger’s head, bloodied him, and repeatedly delivered straight headbutts to a downed “Nature Boy.”
If you watch this match you’ll see how brutal Race was and why he earned the nickname of “Mad Dog.”
Ric Flair endured the punishment and found his opening as he scaled the cage and hit a high crossbody from the top turnbuckle and scored a three count to win his second (or third depending on who you ask) NWA Heavyweight Championship.
This match, while not without flaw, was a great example of why Flair was made the star of Jim Crockett Promotions.
With blood dripping from his snowy white hair and fans refusing to silence Flair celebrated inside the ring with his contemporaries as the first ever Starrcade drew to a close.
“This is the greatest night of my life, and I can’t thank you enough.” -Ric Flair, after defeating Harley Race.
6. RIC FLAIR VS. RANDY SAVAGE (WRESTLEMANIA VIII)
Ric Flair has seriously done it all. Even though he sharpened his teeth under the NWA banner while beginning to cement his legacy in Jim Crockett Promotions, it didn’t stop him from taking a few years away to go visit the McMahon’s company and stand among the other stars of the Federation.
For most of the 1980’s Flair was used by the NWA as the main franchise to combat McMahon’s emerging dominance after going national. So when he left WCW in 1991 there was only one place big enough to hold all of his success and charisma. The WWE.
While Hulk Hogan vs. Ric Flair was supposed to be the main event of WrestleMania VIII I have to admit that this match was better than any Flair/Hogan match, ever. Macho Man was a far better athlete and along with Flair had a very entertaining match.
Like most matches it has a flaw, and this matches flaw is it was just a little too focused on the campy story elements that involved Miss Elizabeth and supposed affair with Ric Flair.
Her involvement at WrestleMania VI was perfect, but at WrestleMania VIII it was a little bit of a tired concept to me.
That takes away very little from the match that should have closed WrestleMania VIII. Even in the early 1990s McMahon was booking the wrong matches to close the show. Hogan and Sid would end the show, but were unable to do anything that eclipsed the match Savage and Flair had.
It won’t be remembered much as a classic WWE Championship match, but to me this was the greatest match of Flair’s WWE career.
He was still capable of putting on a great match and not just a great match for a 50+ year old. Imagine the matches he could have had he never gone back to WCW?
5. RIC FLAIR VS. STING (CLASH OF THE CHAMPIONS I)
Emanating from the very first ever Clash of the Champions event, Flair and Sting kicked off the legacy of not only this important WCW event but a rivalry that would rage off and on for the next 15 years. This was their first ever one-on-one match together.
In the late 1980’s Crockett and McMahon began thumbing their noses at one another by scheduling their events on the same day as one another. Supposedly, this was usually McMahon’s doing.
In retaliation Crockett scheduled the first ever Clash of the Champions which aired for free on television head-to-head against McMahon’s WrestleMania IV! Clash of the Champions would air against WrestleMania the following year as well.
Crockett gave fans a pay-per-view quality show which culminated in this bout for the NWA Heavyweight Championship between, the champion, Ric Flair and, the challenger, Sting.
Getting past the history of the promotion we have a huge main event in which really was the moment we saw Sting established as a cornerstone of the promotion.
Sting came so close to winning his first NWA Heavyweight Championship on this night, but the time limit expired as Sting held in the Scorpion Deathlock.
He did still make himself known as a force to be reckoned with by being capable enough to avoid losing to the “Nature Boy” who was at this point had been the top man in the NWA for some time.
These two legends would go on to have countless rematches for the next 15 years, but to me this match had an air of magic many of their others do not. The only other match of their’s I truly love is their 1994 match from Clash of the Champions XXVII.
After awhile the Sting vs. Flair match began to get a tad redundant, but here it still felt like a spectacle.
Sting and Flair would go on to be cornerstones of the next 35 episodes of Clash of the Champions . It’s inventor, Jim Crockett Jr., however would not.
Even though his ideas were hit-and-miss and he had some of the best talent in the business Crockett had to sell his promotion to Ted Turner who would officially rename the promotion World Championship Wrestling later that year.
4. RIC FLAIR VS. BIG VAN VADER (STARRCADE 1993)
The absolute most fun I’ve ever had watching Vader wrestle. When I think of Vader I typically think of the time frame I was familiar with him which was his late 90’s run in the WWE,
This was better than I could have ever imagined. I openly scoffed when seeing people suggest this match to me, but after watching it from beginning to end I feel like my cynicism was largely misplaced.
Ten years after his epic clash with Harley Race inside of a steel cage Ric Flair returned to WCW to reestablish himself as the true icon of the promotion. Strangely enough, it was Harley Race who accompanied the WCW Heavyweight Champion to the ring on this night in hopes of seeing Flair’s historic career 10 years after he ended Race’s final reign with the NWA Heavyweight Championship
Big Van Vader was at the pinnacle of popularity and Flair was had just returned to the promotion months prior following a stint in the WWE.
Vader, at this point, was a monster of a WCW Heavyweight Champion and was looking to end the career of “The Nature Boy.””
Flair, wrestling smart, yielded the power to the larger man and really put over Vader as a untouchable behemoth.
He ducked, dogged, bobbed, and weaved past every move he could, but still Vader dished out a cavalcade of punishment on the future WWE Hall of Famer.
Flair fought back with immeasurable intensity and his hometown crowd went wild every time he got on the offensive side of things.
The finish was a tad awkward, but the crowd went bloody nuts for “Naitch” when he quickly pinned Big Van Vader before he could fling the North Carolinian off his barrel chest.
Fireworks, confetti, and tears accompanied the roars of the crowd. This match was a really different type of main event match for Flair. Typically he wrestled men around his own size, but here fans had the opportunity to see what he could do with a man he couldn’t wrestle in the traditional sense.
3. RIC FLAIR VS. RICKY STEAMBOAT (CLASH OF THE CHAMPIONS VI)
This was the second match from the now legendary trilogy of matches between Ricky “The Dragon” Steamboat and “Nature Boy” Ric Flair in 1989.
This was the rematch for the NWA Heavyweight Championship which Flair and lost to Steamboat at Chi-Town Rumble four months earlier. This was also a Two out of Three Falls match.
It also might be one of the most bearable hour long matches I’ve seen. Often the matches drag on, but since this not a case of the match having a time limit it actually felt very natural.
“The Dragon” and the “Nature Boy” put on an exhibition of drama, pacing, technical skill, and entertainment every moments of the match.
While both men are wrestlers in a very traditional scene they sneaked in several very innovate and interesting spots in the match.
Flair won the first fall, with Steamboat getting the second and third allowing him to retain his NWA Heavyweight Championship belt after the two men went back and forth for almost 60 minutes.
The thing was, Flair’s foot was under the bottom rope during this final pin fall. This discrepancy would lead to the third and final match of the series.
Flair’s final opportunity at Ricky “The Dragon” Steamboat would occur at WrestleWar 1989 just one month after this contest. The trio of matches have gone down in history as some of the most revered displays of showmanship and skill.
Any man or woman who wants to become a professional wrestler should watch this series of matches before they even put on their boots.
2. RIC FLAIR VS. TERRY FUNK (CLASH OF THE CHAMPIONS IX)
Terry Funk may be more well known now as a mad man who did moonsaults at 52 years old in ECW, but the soft spoken Texan is far and away one of the greatest professional wrestlers to ever live. He has stood in the rings of more promotions than you could number and is in more wrestling Hall of Fames than just about anyone.
With a dream team of Jim Ross and Gordon Sollie on announcing duties the two legends competed in an I Quit match following the fallout of the very first ever Halloween Havoc in which Flair and Sting defeated Terry Funk and his partner, The Great Muta.
While these two are often thought of when younger professional wrestlers mentioned the “old men who never know when to hang it up” Funk and Flair, at this stage, could still deliver some of the most captivating matches of the time.
Funk was brilliant in this contest and exhibited a lot of brutality and viciousness here.
The challenger, Funk, brought offense that really fit the structure of the I Quit match and also brought in moves like the piledriver that just looked sickening.
Flair, not be outdone by anyone, had his fair share of extreme action too. Slamming Funk’s head into the back of a wooden table and suicide diving onto his back whilst escaping around the ring.
After fending off Funk, Flair began to focus all of his offense on the knees and legs of Terry Funk. Wearing him down in preparation for the Figure Four Leg Lock.
Terry avoided it for as long as he could, but eventually the “Nature Boy” found his opening and locked it in. Funk repeatedly shouted “Never!” as the referee asked him if he wanted to give up.
Finally, Funk relented and screamed “I quit” after he could neither reverse or escape the hold.
This match was probably as close to hardcore as the classic NWA ever got. It felt really unique compared to the other matches on the card that night. While it may have been a gimmick match, Flair and Funk still brought logic and ring psychology to the contest.
1. RIC FLAIR VS. RICKY STEAMBOAT (WRESTLEWAR 1989)
Many regard the match I listed at number three to be their best encounter, but from my point of view I cannot see how anyone ranks their television match over this. The conclusion to what is probably the greatest wrestling trilogy of all time.
While their match at Clash of the Champions was much longer, that does not make it the best encounter. At WrestleWar they exceeded anything and everything they did before and since.
To me, this match personifies professional wrestling in its purist form.
If you don’t think you are a fan of Ric Flair I implore you to watch this match, uninterrupted, in full. This match ranks right among my favorite matches of all time.
This was Flair’s final opportunity at the World Heavyweight Champion, Ricky Steamboat.
In 1989 the Jim Crockett Promotions was trying very hard to maintain professional wrestling’s image as a “sport.” There were “judges” and 15 minute “rounds” and it all just sounds silly in hindsight. While this match lacks much of the glitz and glamour that could be found in the WWE at this time what you got was wrestling.
When I say wrestling it may make it sound ordinary, but you have to realize these are two of the best scientific wrestlers to ever live. Flair brought tradition, pacing, and drama to the match and Steamboat was able to keep the match from dragging, and added some high octane offense to the match.
You have iconic matches like Hogan/Andre, Michaels/Taker, and Austin/Rock, but for me the most iconic rivalry off all time might well be “The Nature Boy” Ric Flair versus Ricky “The Dragon” Steamboat.
It’s tradition personified. It is everything that made Ric Flair – Ric Flair.
In 2009, Ric Flair inducted Ricky Steamboat into the WWE Hall of Fame. At the ceremony the two locked up one final time.