Ric Flair's Most Memorable Matches Of All Time Ranked

Any conversations about the greatest pro wrestlers of all time have to include Ric Flair, and a great many fans would put him atop their list in those discussions. Born in 1949, Flair didn't make his pro wrestling debut until 1971. But, in 1975, he was Flair was injured in a plane crash, which necessitated a change to his wrestling style. That's when he adopted the "Nature Boy" persona — a heel gimmick borrowed from Buddy Rogers of the previous generation. "Nature Boy" Ric Flair was known for being a rich and cocky womanizer but also a ruthless competitor willing to do whatever was necessary to win a wrestling match. He famously described himself as a "styling, profiling, limousine-riding, jet-flying, kiss-stealing, wheeling, dealing son of a gun" and has had many a legendary feud in his pro wrestling career.

Obviously, Ric Flair's career has gone on for half a century, and he didn't even pretend to retire until 2008, so there were way more noteworthy matches than we can fit onto one list. He fought Dusty Rhodes and Terry Funk each several times, for example, but we've only included the best match from each feud. He also had some great matches with Barry Windham that didn't quite make the list. Don't worry, though, you'll find that Ricky "The Dragon" Steamboat is well represented. So without further delay, let's count down Ric Flair's 15 most memorable matches.

15. Ric Flair (c) vs Lex Luger for the NWA World Heavyweight Championship (WCW WrestleWar 1990)

Of all the things Lex Luger was remembered for as a star for both WCW and WWF in the late 80s and into the 90s, being a top in-ring worker was not one of them. A former pro football player, he was one of the many talents who seemed to be pushed primarily due to his muscular physique. That said, Ric Flair could put on a good match with a broomstick. And, while Flair's matches never really focused on displays of athleticism, his panache for storytelling helped elevate their contest at WrestleWar to be one of Luger's best matches, despite its disappointing ending.

With Flair accompanied by his valet Woman, the champ threw everything but the kitchen sink at "The Total Package," but little of it even registered with Luger as he shrugged off Flair's attempts at offense. Luger had a clear strength advantage and dominated Flair with his power throughout the match. The "Nature Boy" did manage to weaken Luger's leg at one point, working the injury to eventually lock in his patented Figure-Four Leglock. Then Luger's best friend Sting came down to the ring, encouraging his pal to not give up and fight back. Luger was able to mount a comeback, but once the referee was accidentally knocked out, all hell breaks loose. 

Luger had Flair pinned for a sure victory, but there was no ref to count it. He even managed to get Flair up in his Torture Rack backbreaker, and, with the ref coming to, Flair's Four Horsemen cohorts Arn and Ole Anderson hit ringside to assault Sting. "The Total Package" went to fight off the attackers and help his buddy, but this distraction caused Luger to be counted out of the match. Flair walked away with the victory and kept the title around his waist. Not the best of endings, but it's a solid match up until that point. 

14. Loser Leaves Town Match: Ric Flair vs Mr. Perfect (Monday Night Raw: January 25, 1993)

Near the very beginning of "Monday Night Raw" came this memorable television match that brought about the end of Ric Flair's first run in the WWF (he was on his way back to WCW), as he faced his former manager Curt Hennig, aka Mr. Perfect. Hennig was a little off his game in this one compared to some of his other matches around the same time, but even a slightly less than flawless Perfect could deliver a better match than most. 

Flair threw every dirty trick in his book at Mr. Perfect, but Hennig and his impeccable ring IQ had an answer for all of it. Perfect seemed to have the advantage over Flair as the match got going, but then Flair managed to throw Perfect out of the ring, leaving him bloodied. Flair caught Hennig in more than one hold, but Mr. Perfect always managed to escape. The only exception was the Figure Four, but the referee broke it up because Flair was leaning on the rope, making the hold illegal. Flair got a lot of near-falls, but Hennig always kicked out. As Flair grew increasingly frustrated with his inability to gain an advantage over Mr. Perfect, it became obvious that never quite meshed with WWF in this period. Flair might be a sequin-robed Nature Boy, but he's also a regular man, and this cartoonish world of Vince McMahon's making was populated with over-the top demigods. So when Mr. Perfect hit Flair with the Perfect-Plex, pinning him and sending him out of WWF, it was no tragedy. As long as WCW remained in existence, that was where Flair truly belonged, and he was on his way home. 

13. Vader (c) vs Ric Flair for the WCW World Heavyweight Championship (Starrcade 1993)

It's hard to imagine two wrestlers more different than Ric Flair and Vader. Vader was a unique combination all on his own — a monster of a man with shocking agility for someone his size. Flair, on the other hand, is much smaller in physical stature, relying more on his cutthroat guile to win championships, even as a babyface like he was in this match. He'd just recently returned from his time in WWF, and the WCW crowd was incredibly excited to see him. One person who was not excited was Harley Race, Vader's manager. He'd been Flair's opponent at the first Starrcade, 10 years earlier, and he'd have loved to see the big guy destroy the Nature Boy, as Race had once failed to do.

It was clear just from looking at them that Flair was no match for Vader physically, and it was quickly borne out as Vader got things going by punching the stuffing out of the Nature Boy and basically tossing him around like he weighed nothing. Flair kept chopping Vader, but Vader wasn't even bothered. Even when Ric managed to knock him down, Vader got right back up. Flair eventually lost patience and started throwing everything he had at Vader, even biting him. Flair finally managed to lock in a Figure Four, while Harley Race completely freaked out at ringside. Vader got to the ropes to break the hold, and then went for a moonsault, but Flair got out of his way. The tide turned, finally Ric managed to knock Vader's legs out from under him and roll him up for a pin. For a babyface Ric Flair, it wasn't the most inspiring victory, but the important thing is that he managed to get one over on a bigger, stronger, and possibly even smarter opponent.

12. Ric Flair (c) vs Sting for the NWA World Heavyweight Championship (WCW Great American Bash 1990)

Sting, WCW's top rising star of the late '80s, was a different sort of character — more of a colorful superhero than the sort of dangerous-looking tough guys whose domain the company had traditionally been. He was the kind of kid-friendly babyface that was associated more with WWF, even though he was a WCW guy through and through. This match was meant to be a passing of the torch, as Sting, the WCW star of the '90s, took the World Heavyweight Championship from Ric Flair, the NWA/WCW star of the '80s. 

The match was a bit of a showcase for both stars to get all their stuff in, so naturally it started with Flair's chops. Sting quickly overcame them and showed what he could do, press slamming Flair to turn the tide. He knocked Flair out of the ring with a beautiful dropkick, then knocked him back inside with a clothesline. Meanwhile, Ric seemed to be having a hard time hurting his younger opponent. He suplexed him, he even knocked him into the guardrail outside the ring, but Sting seemed unfazed. When Flair started working the leg to prepare for the Figure Four, Sting responded by locking in the Figure Four on Flair! Then when Flair tried the hold on Sting, Sting kicked his way out of it. When Sting locked in his own signature hold, the Scorpion Death Lock, Flair's loyal Horsemen ran in. Sting's heroic friends, the delightfully named Dudes with Attitude, stopped the Horsemen from interfering, but the distraction gave Ric the moment he needs to get to the ropes. He tried the Figure Four again, but Sting countered it into a Small Package and won the NWA Championship.

Flair would win it back, of course — he always did — but the landscape was clearly changing. Within a year Flair would be off on his sojourn to WWF, and WCW would look a lot different by the time he came back. Sting would stick around, though, and become even more inseparable from the WCW brand.

11. Steel Cage Match for the NWA World Heavyweight Championship: Harley Race (c) vs Ric Flair (Starrcade 1983)

The first Starrcade, the first major CCTV show (what would soon evolve into pay-per-views) would inspire WrestleMania a couple of years later. If WrestleMania 1985 kicked off the 1980s wrestling boom, you could call Starrcade 1983 the soft launch. As the territory era was drawing to a close, Dusty Rhodes and the Crocketts put together an amazing wrestling supercard, and then made it so anyone in the country who wanted to watch it could. The world would never be the same.

You might not think a match that's about four decades old would hold up to modern fans' standards, but if you can accept the usual '80s rest holds and so forth, this one is pretty great. Harley Race is an old school villain in the aforementioned "dangerous-looking tough guy" mold, and it's a chance to see a young Flair work as a babyface. The build featured that promo you may have seen, in which Harley put out a bounty on Ric Flair's head, which made it easy to cheer on the Nature Boy.

Since Harley's viciousness has already been established, it's no surprise that this match was largely about how much punishment the Nature Boy could take. Whereas Flair started the match with impeccable mat work, Race just kept kneeing him in the head and neck to set up his Piledriver finisher. At one point Harley drove Ric's head into the cage and blood spattered on the camera, which really made the match feel nasty in a good way. The referee kept having to physically pull Race off of Flair when he got too brutal, which is often the only moment Flair had to get some offense in before Race came at him again. He did manage to knock Harley's head into the cage and the tide briefly turned when Flair locked in the Figure Four, but Race managed to get to the ropes. Harley hit a flying headbutt, and Ric looked just about finished. But then the ref accidentally took a second headbutt meant for Flair, and the Nature Boy seized the opportunity to go up to the top rope and hit a flying body press for the pin. A whole bunch of babyfaces came out to celebrate with Flair, which really made it feel that much more like the coronation of Ric Flair as the NWA star of the 1980s.

10. Ric Flair (c) vs Randy Savage (WrestleMania 8) for the WWF World Championship

If you want to know what it was like to be Ric Flair and Randy Savage in WWF in 1992, this match for the World Championship happened in the midcard. The other great match at 'Mania 8 was Rowdy Roddy Piper versus Bret Hart for the Intercontinental Championship, and it went on earlier than this one.

The other thing we need to get out of the way about this match is the story of their feud, which has not aged well, to say the least. Supposedly Flair and his cronies Bobby Heenan and Mr. Perfect had nude photographs of Macho Man's wife, Miss Elizabeth, which they were threatening to show the world. Pretty despicable. It's hard to understand how Randy Savage beating up Ric Flair and taking the title from him would solve the problem of Elizabeth's leaked nudes, but it's easy to understand why Macho Man would think the beating was an appealing idea.

Of course, none of that matters all that much once the bell rang, because you got to watch two of the greatest wrestlers of their era go at it on the grandest stage of them all. Macho Man was an angry babyface, while Flair was a cold, methodical heel. The crowd was completely behind Savage, of course, especially when Flair started beating the tar out of him, just to make a point. So naturally they exploded when Randy rallied and threw Ric over the top rope. When Savage hit his Flying Elbow Drop, that should have been the end, but Mr. Perfect pulled him off Flair before the ref could count three. Randy chased Perfect, knocking down the ref in the process, which gave the Nature Boy a chance to hit Macho Man in the face with a foreign object Perfect had slipped him. Somehow, Savage kicked out just before the ref counted to three. Then Miss Elizabeth ran in, which distracts Flair at just the wrong moment. He couldn't resist giving her a leer and yelling,"This one's for you, baby! Wooo!" Savage took the opportunity to punch Flair and then roll him up for the three-count. Ric tried to be affectionate with Elizabeth, but she slaps him in the face and celebrates with her Macho Man, the new WWF Champion.

9. WarGames: Ric Flair, Barry Windham, Sid Vicious, and Larry Zbyszko vs Sting, Brian Pillman and The Steiner Brothers (WCW WrestleWar 1991)

Every WarGames match is an exercise in chaos. The rules can seem complicated, but they only exist to create an ever-mounting scenario in which two guys fighting becomes three guys fighting, and the numbers increase until eight or ten men are crowded into that double-sized cage beating the absolute tar out of each other until somebody submits. The 1991 War Games match isn't the very best of them (that would come in '92), but it's a strong early contender, and definitely the best in which Flair was involved.

Brian Pillman and Barry Windham were first into the cage, and Pillman quickly got the better of Windham despite being the smaller man. Unfortunately, "Flyin'" Brian couldn't really fly because the cage roof was so low, a problem that would soon get worse for him. Flair entered third, and Pillman found himself at a disadvantage against the two larger men. Once all eight men filled the cage, Sting's team got their opponents in quadruple Figure Fours, but Flair broke it up and turned the tide for the heels. While everyone else was fighting on the other side of the cage, Sid attempted to powerbomb Brian Pillman, but Pillman hits the top of the cage, which caused Sid to drop him on his head. For good measure, Sid powerbombed him again, and Brian looked to be completely out.

Pillman's injury led into the match's strange ending, which is the main factor working against this match. The genuinely enormous man known as El Gigante ran in, entering the cage and rescuing Brian, submitting on his behalf and then carrying him to the back in his arms like a helpful Frankenstein's monster.

8. Ric Flair vs Shawn Michaels (WrestleMania 24)

In 2008, with Flair obviously nearing the end of his career, WWE ran a storyline in which Vince McMahon informed the Nature Boy that he'd be forced to retire the next time he lost a match. Naturally, he won a number of matches before running up against HBK in the buildup to this WrestleMania bout. Shawn didn't really seem to want to be the one to retire Ric Flair, but as Mister WrestleMania, it was his responsibility.

Flair was 59 at the time, but he acquitted himself well. He even had some big moves left in him, like slamming Shawn from the top rope and hitting the same flying cross body that he used to beat Harley Race a quarter-century earlier. As the match went on, though, Flair was getting noticeably warn down, and Michaels started to look like a man who's been asked to beat up an old dog. His hesitation gave Ric the chance to trip him and lock in a Figure Four, but Shawn reversed it. Flair took Shawn's finisher, Sweet Chin Music, but Shawn was too slow with the pin, and Flair kicked out. Flair seemed to be getting the upper hand with a series of chops, but Michaels ended that with a superkick. With Flair barely able to stand, Michaels mouths, "I'm sorry; I love you," and hit Sweet Chin Music again to seemingly end Flair's career.

The Nature Boy would go on to have more matches outside of WWE, but the less said about those, the better. Even if this isn't really Flair's last match, it's certainly his last match that made this list.

7. Royal Rumble 1992

Widely regarded as the best Royal Rumble ever, 1992's battle royale told a story about Ric Flair. The WWF World Championship was on the line in this Rumble, as it had been stripped from Hulk Hogan over a controversy involving his matches with the Undertaker. That turned out to be a perfect opportunity for Ric Flair, who'd arrived in WWF the previous summer, calling himself "the Real World's Champion." Flair entered the match third, meaning he'd have to last for about an hour to have a shot at winning the belt. That's exactly what he did, proving himself to the WWF audience, many of whom didn't know him well, as both a worker and a character.

Bobby Heenan also played a key role in the match. He was both Flair's manager (along with Mr. Perfect) and a color commentator on the show, and the idea was that he had money riding on a Flair win, so he spent the entire match openly cheering on the Nature Boy, and complaining when things weren't going his way—"That's not fair to Flair!" became a catchphrase. 

There's no better introduction to the WWF roster of any given year than the Royal Rumble, so this was an opportunity for Flair to share the ring with guys like Shawn Michaels, Roddy Piper, the Undertaker, and of course Hulk Hogan. Flair had a good showing over the course of the hour, eliminating the British Bulldog, the Big Boss Man, Kerry "Texas Tornado" Von Erich, and Randy Savage. Of course Hulk Hogan, never in a hurry to make another guy look good, helped Flair eliminate his final opponent, Sid Justice, who had just eliminated the Hulkster. But Flair still came out of this looking great, delivering his classic "with a tear in my eye" promo with his new belt in hand.

6. Ric Flair (c) vs Dusty Rhodes for the NWA World Heavyweight Championship (Starrcade 1985: The Gathering)

Even if you haven't seen this match, you've probably seen at least one promo that led up to it. This is the match that pays off Dusty Rhodes' classic "Hard Times" promo, in which the American Dream, just back from injury, promises to win the World Heavyweight Championship from Ric Flair in the name of all the working class Americans who were suffering economically in the Reagan era. Dusty had always been a working class hero (despite an occasional penchant for fur coats), but this feud brought things into sharp relief — Dusty embodied blue-collar America, while Ric Flair was all about his limousines, jet planes, and expensive shoes. That's why Ric Flair had to lose.

The match started slowly, with the two circling each other cautiously, but their personal animosity came out soon enough, and things got more aggressive. Dusty was serious about defeating Flair, but being the American Dream, he still found time to dance a little. At one point the ref got knocked out, which gave Arn and Ole Anderson a chance to run in and attack Dusty. Flair attempted a pin, but Dusty kicked out. He rolled up the Nature Boy with a Small Package, and won the NWA Championship. The Andersons' interference would cause officials to later overturn the win, making it a disqualification, in which the title doesn't change hands.

5. Ric Flair (c) vs Ricky Steamboat for the NWA World Heavyweight Championship (NWA Chi-Town Rumble 1989)

This is the first of three classic matches that occurred in 1989 between pro wrestling's two greatest Richards (with apologies to Rude and Steiner), and all three matches made this list. Ricky "The Dragon" Steamboat was a babyface who entered with his wife and son, and was sold by the commentary team as a working class hero, in contrast to Flair's private school background and glamorous "jet-flying" lifestyle. 

The two had fought in the past, so Ricky came into this match with an understanding of just how tough and wily the Nature Boy could be. He wasted no time in upping his aggression, trying to pin Flair multiple times almost as soon as the match starts. Whenever Steamboat seemed to be getting the better of Flair through pure wrestling skill, Flair regained the advantage through heel shenanigans. The Nature Boy was shameless, grabbing a handful of tights for every pin attempt, except when he put both his feet on the second rope instead, for that magical but illegal "leverage" that makes pins more effective. That never stopped Steamboat from kicking out, however, and responding with headlock takeovers and the like. When Flair put Steamboat in the Figure Four, Ricky grabbed the ref's arms desperately, as if begging for a way out of the hold, but of course he ultimately had to escape himself.

The ref got knocked out by an errant flying chop, so there was nobody to count when Steamboat first pinned Flair, but then Flair managed to pin Steamboat, and there's still no ref to count. Ric attempted the Figure Four just as a new ref was arriving, but Ricky reversed it and rolled Flair up to win the NWA World Championship.

4. Ric Flair (c) vs Sting for the NWA World Heavyweight Championship (NWA Clash of the Champions 1, 1988)

If the match from 1990's Great American Bash was a passing of the torch, this 1988 match was the moment it became clear who was next in line. Flair was a master at making his opponents look great even when they didn't win. As a traveling NWA Champion of the territory era, that was his primary job. He'd show up in a town, accept a challenge for the title by that town's local hero, and then he'd prove to those fans just how good their local hero really was, without dropping the belt to him. But "Clash of the Champions" was televised nationwide, and Sting was positioned as America's local hero. 

The match was a tale of canny experience against youthful energy and skill. Flair seemed to have a clear advantage early on, but Sting began to turn the tide with a Scorpion Deathlock. When Ric managed to catch Sting in the Figure Four, even using the ropes for leverage behind the ref's back, Sting reversed the hold and escapes anyway. As the match went on, Sting proved just how good he was, but the Nature Boy seemed to realize that the clock will run out before long, and all he had to do to hold onto his title is survive Sting, not necessarily beat him. Flair avoided the Stinger Splash, and Sting lost precious time recovering on the outside. Flair hit his flying crossbody, but Sting reversed it for a two-count. Finally, Sting got Ric in another Scorpion Deathlock, but there were only 30 seconds left on the clock. Flair endured the pain until the bell, retaining the NWA Championship in a draw.

3. I Quit Match: Ric Flair vs Terry Funk (NWA Clash Of The Champions 9, 1989)

Terry Funk had been tormenting Ric Flair for months by the time of this match in November 1989. Funk had even managed to turn the Nature Boy babyface by piledriving him through a table. They'd already faced each other more than once, but an "I Quit" match was the only thing that could possibly put their animosity for each other to bed. In contrast to Flair's feud with Steamboat earlier that year, which had been a showcase of remarkable wrestling, Flair vs Funk was all about violence. In his long career, Terry Funk proved he could do a great many things, but he was always at his best as the unhinged hardcore brawler who turns up for this match.

Flair knew how intense Funk could be, so he upped his own level of aggression, taking every opportunity to choke funk, or chop him so hard he flew over the top rope to the floor. For his part, Terry just kept beating Ric about the head with the microphone. After he took a pretty bad beating, Funk and the ref tried to get Flair to quit, but he refused. An angry Funk hit a piledriver in the ring, and then a second one on the floor. Flair again refused to quit, and tapped into his last reserves of energy to turn the tide. It took him a while to get Funk locked in the Figure Four, but once he did, after all the damage they'd taken, Funk looked like it was killing him. He first refused to quit, but then screamed that his leg is breaking and says, "Yes, I quit." After the Nature Boy won, Terry Funk shook his hand in respect, a rare sight after so brutal a match.

2. Two Out Of Three Falls Match for the NWA World Heavyweight Championship Ricky Steamboat (c) vs Ric Flair (NWA Clash Of The Champions 6, 1989)

Flair got his rematch against Ricky Steamboat a couple of months after losing the championship, challenging him to a two-out-of-three-falls match.

The match started out much like their last one, trading Ricky's headlocks for Ric's Figure Four. This time, however, the aggression was such that they started slapping each other in the face while Flair had Steamboat locked in the hold. Flair also worked Steamboat's leg, banging it repeatedly against the ring apron ("the hardest part of the ring," as Jim Ross is fond of saying). Before anything came of that effort, however, Ric had a chance to reverse Ricky's attempt at an inside cradle, and managed to get the first fall that way.

For the second fall, Ricky Steamboat managed to do something nobody in the NWA had ever done — force Ric Flair to submit. Specifically, he pinned both his arms back in a double chickenwing, and Flair couldn't find a way out. With the two evenly matched, the third fall naturally became the hardest fought, taking about as long as the first two combined. Having submitted Flair once, Steamboat hoped to do it again, but that's where things got messy. Flair avoided the chickenwing, but both men tumbled to the mat. Steamboat managed to get a shoulder up while Flair's stayed down and the Dragon retained the championship.

Unfortunately for Steamboat, a replay showed that Flair's foot was under the rope. It wasn't enough to reverse the result, but it was enough to get Flair another rematch.

1. Ricky Steamboat (c) vs Ric Flair for the NWA World Heavyweight Championship (NWA WrestleWar 1989)

Part of what makes the Flair/Steamboat series such a classic is that the wrestling changes to fit the story. By this third match, Flair is as serious as he's ever been. At this point in his career, Flair was defined by never being that far from the championship. This was his second rematch, which he only got because of a technicality. If he were to lose to Steamboat again, he probably wouldn't get another chance anytime soon. So on the road to WrestleWar, the Nature Boy put his ego aside and focused on the wrestling. He showed up more technical than we usually see from Flair, especially as a heel.

It started with multiple collar-elbow tie-ups. When it turned to chops, Ric hit as hard and as precisely as he ever had, knocking Ricky down with a single chop more than once. Meanwhile, Ricky Steamboat was hoping to repeat the rare feat he achieved in their last match by getting Flair to submit to the double chickenwing. Flair knew what was coming, though, and blocked the hold by weaving his legs through the ring ropes. Ric was still as nasty as ever, of course, especially when he turned to argue with the ref about a pin attempt, and just casually put his knee down on Ricky's neck as he did so. On one hand, there was a real sense that the Dragon might have the Nature Boy's number, but that was balanced out by Flair's willingness to grab every opportunity and do just about any terrible thing. 

When Flair finally won, it almost seems like dumb luck, as he managed to reverse a body slam into an inside cradle. But that luck is as part of who Ric Flair is, as much as the in-ring prowess, the mic skills, and the dirty tricks.