WOOOOO! Anyone who calls themselves a fan of sports entertainment knows there’s one man who stands above all them as the limousine riding, Learjet flying, kiss stealing, wheeling and dealing son of a gun who just so happened to be the greatest wrestler in the world. Well, at least they know how Ric Flair chooses to describe himself anyway, though millions of fans surely do agree with The Nature Boy’s assessment of his talent and place in wrestling history.

By and large, it looks like WWE agrees, making Flair the only man inducted to their Hall of Fame twice. Outside of the WWE Universe, Flair’s reputation is even better. Officially speaking, he has 16 World Championships to his name, yet according to Naitch’s own count, the number is closer to 25, far and away destroying his closest competitor’s in this regard.

Ultimately, we could sit here all day listing the reasons Flair deserves all the praise he’s received and more, but let’s be honest: nobody’s perfect, and there’s just too much wrestling out there for any one person to be considered the unquestionable best grappler in history. Like anyone else, Flair has his detractors, and quite frankly, some of their points arguing against him are even valid. Keep reading and decide for yourself where you land on The Nature Boy’s iconic legacy with these 8 reasons he’s the greatest wrestler of all time alongside 7 counterpoints suggesting he might not be.

15 15. GREATEST: Diamonds Are Forever, And So Is Ric Flair

Since this list is 50% about proving Ric Flair’s assertion correct that he’s the greatest of all time, let’s start off with some words from The Nature Boy himself. As the iconic wrestler stated countless times while defending the NWA Championship against one scrub after another, “Diamonds are forever, and so is Ric Flair.” More than a simple comparison to an expensive and luxurious material, Flair was boasting about the fact he planned on staying in the sports entertainment business and performing at a high level his entire life, a goal he most certainly accomplished. Flair’s first NWA Championship came in his early 30s, and his final run with the Big Gold Belt at WCW didn’t happen until he was 50. On top of that, there was another decade of success as a manager and mentor figure in WWE, all building to a career that’s literally unmatchable without two-dozen-years worth of effort.

14 14. JUST GOOD: He Stuck Around Way Too Long

Appropriately representing the duality of this list, our first criticism of Ric Flair’s career is suspiciously similar to one of the positives. On the one hand, Flair’s ability to stay in the main event longer than just about anyone else and delivering classic matches while doing so is indeed iconic in and of itself. Unfortunately, Flair would have been able to achieve this same status had he retired a solid 15 years earlier than he did. The last five in particular, spent in Total Nonstop Action, were basically The Nature Boy destroying his own legacy match by match. Does any of this make his prior accomplishments less spectacular? Of course not. But, it does mean that when presented in totality, parts of Flair’s career were pretty horrible to watch, especially for his biggest fans. Even if he was the best wrestler of all time at one point, the reputation certainly didn’t stand his entire time in the ring.

13 13. GREATEST: He Led The Four Horsemen

Not even The Nature Boy achieved everything he won throughout his incredible career all by himself. In the beginning, Flair had tag team partners like Greg Valentine and Blackjack Mulligan backing him up, and later on he formed arguably the most iconic stable in wrestling history: The Four Horsemen. Over the years, there would be far more than four members to this iconic outfit, yet the one constant holding the so-called elite of pro wrestling together was Ric Flair. In fact, Flair’s presence is what assured that elite status would be upheld, as the whole point of the group was often to back up the NWA/WCW World Champion. Truly great wrestlers need to have versatility, showing the ability to excel in singles, tag team, or larger style matches, and with the Horsemen, Flair accomplished all of that and more.

12 12. JUST GOOD: WCW Dragged Him Through The Mud

Continuing on the trend that Ric Flair had too many bad years to unquestionably get called the best wrestler of all, let’s also not forget that even some of his good years were loaded with terrible ideas. Unsurprisingly, this is because Flair spent the later years of his prime in World Championship Wrestling, a company notorious for mismanaging top talent and creating really stupid sports entertainment in general. Flair was victim to this like anyone else on the roster, enduring angles that saw him regularly strip to his underwear in the middle of the ring for no reason, and that’s when he wasn’t dressing up like a woman to, uh, confuse Hulk Hogan? But somehow it made Hogan win the match Flair dressed in drag during, which was pretty much the pattern every time those two icons crossed paths, an occurrence that happened constantly in the late ‘90s. It’s hard to call Flair’s legacy perfect knowing he spent almost a full decade accepting this sort of ridiculous treatment.

11 11. GREATEST: He Lived His Character

Experts have long held that the best wrestling characters are the ones closest to the real life personalities of the performer playing the role. In this respect, Ric Flair truly was one of the best of the best, only bragging about all night parties with hundreds of nameless women because that’s what he actually did every time he won a World Championship. The Nature Boy character was a monument to excess, and Flair made sure fans knew full well he lived out that trait in every way possible. Flair really rode in stretch limousines, entered arenas in helicopters he no doubt transferred into out of a Learjet, and you better believe there were stolen kisses of one form or another scattered all throughout his life. This added an extra verisimilitude and realistic edge to everything Flair accomplished inside the ring, absolutely essential qualities for any top level sports entertainer.

10 10. JUST GOOD: He Lived His Character Too Well

Of course, there is such a thing as a performer getting too into their characters—especially when that role requires them consuming massive amounts of alcohol on top of other questionable behavior in general. Even staying up all night to party before hitting the gym isn’t all that great for one’s body, and this was practically the mildest issue with Ric Flair’s lifestyle. The real problem with The Nature Boy living his character is that what can sound like an extravagant athlete in one regard is shockingly similar to a run-of-the-mill severe alcoholic in another. While a smart performer would realize when to quit and where to draw the line between real life and mere character, Flair was completely incapable of separating who he was as a man from who he was as a wrestler. In some respects, this is another issue that doesn’t necessarily effect his legacy in the ring, though it does bring into question his skills as a performer.

9 9. GREATEST: 16-25 Reasons Why

According to the official WWE record book, Ric Flair co-holds the record for most World Championships won in a single career with 16 reigns, an achievement he shares with John Cena. When one includes a handful of technicalities WWE merged into one reign plus a few titles not even the NWA recognizes anymore for some reason, the number can reach as high as 25 runs with the most important prize in sports entertainment. This puts Flair nine ahead of Cena, and almost a dozen above the next closest competition after that. Flair’s number of championships is so impressive that way to look at this information would be to forget the other half of our list entirely and consider the debate settled on this fact alone. That said, Flair’s countless runs with the World Championship also mean that he lost this grand prize 25 times, as well, a huge number of high profile losses for “the best in history.”

8 8. JUST GOOD: Barely A Year Of His Peak Was Spent In WWE

For as great as it sounds to say Ric Flair won 25 World Championships throughout his career, there is an unfortunate asterisk next to that number calling most of them slightly into question. Only two of Flair’s runs with the World title took place in WWE, during the single year he spent there still in his prime. The rest of Flair’s time in WWE was at best a denouement, offering fans diminishing returns with occasionally drops of greatness, at best. Considering WWE was the top company in wrestling pretty much the entire time Flair was around, it hurts his all-time legacy just a little bit that he barely spent any time in the company during his prime years. This isn’t to say nothing that happens outside of WWE matters, but let’s face it—even a curtain jerker working for Vince McMahon is more famous than a wrestler working almost anywhere else. Not that Flair couldn’t have been a huge star for Vince the whole time, as he probably could have, but the fact remains he didn’t, and it does hurt his place in history just a little bit.

7 7. GREATEST: His Matches Were The Best In History

All right, let’s just jump to the chase with this whole Ric Flair is the greatest of all time argument and start dishing out some specifics. It’s all well and good to say the guy wrestled in countless great matches, but that’s meaningless without the evidence to back it up. Luckily, that evidence is available on the WWE Network and elsewhere in their wide catalogue of releases, so here’s a few places to start. Anyone needing a crash course on Ric Flair’s greatness, check out his performances against Harley Race in 1983, the Von Erich brothers throughout the mid-'80s, Barry Windham in 1987, Sting in 1988, Ricky Steamboat in 1989, and let’s not forget the 1992 Royal Rumble. Matter of fact, pretty much any other individual bout Flair wrestled from the late-1970s into the early-1990s was bound to be a classic. We’ll even through in the series against Randy Savage circa 1995 as his last hurrah of constant five-star classics. No other athlete has a list this long.

6 6. JUST GOOD: Too Many Of His Matches Were Similar

On paper, the long held cliché that Ric Flair could “wrestle a broomstick and produce a three-star match” was used as the ultimate sign of his greatness. Back in the 1980s, it was indeed true that on any given night Flair could wrestle practically any person on the card and create something worth watching, yet this came with an unexpected downside in that a whole lot of these matches look outrageously similar in retrospect. Granted, the same thing could be said about just about any wrestler at Flair’s level, as they inevitably stumble upon a winning formula and see no reason to mess with it. For the Nature Boy, that was taking loads of punishment before regaining the advantage through nefarious means and then doling out large amounts of pain himself en route to a cheap victory. While it worked every time, Flair’s legacy would be a little more fun to rewatch if he switched it up a little bit more often.

5 5. GREATEST: He Overcame Incredible Injuries

Being a pro wrestler, it was inevitable that Ric Flair would get hurt at some point in his career, and possibly in horrific fashion. However, it was extremely bad luck for him to suffer the worst accident of his life right when things were getting started, one of four victims in a small plane crash that occurred way back in 1975. Flair’s back was broken in several places due to the crash, and doctors suggested he may never wrestle again. Instead, he overcame all odds and persevered, redeveloping his wrestling style and the course of the sport’s history in the process. Thinking about how much Flair overcame just to step inside a wrestling ring adds that much more to his legacy at large, possibly enough so to push him over the edge and truly make him the best of all time.

4 4. JUST GOOD: He Never Main Evented WrestleMania

Truth be told, merely having spent most of his career away from Vince McMahon’s influence couldn’t have effected Ric Flair’s legacy all that badly. If anything, Flair probably found some advantages in staying away from the maniacal WWE CEO, never having to go through any of his craziest storylines or get pushed down the card unfairly. Well, almost anyway, as Flair really should have main evented WrestleMania once, and yet one argument against his legacy is the fact he never did. While Flair defended the WWE Championship against Randy Savage at WrestleMania VIII, Hulk Hogan and Sid Justice headlined, and The Nature Boy was never near that position again. Of course, Flair did main event a record number of Starrcades, the WCW equivalent to the Grandest Stage of Them All, but the fact remains he never achieved sports entertainment’s greatest spotlight.

3 3. GREATEST: His Outstanding Rivalries

In all honestly, Ric Flair’s greatest matches could be viewed entirely on their own merit, and The Nature Boy would still deserve recognition as one of the greatest wrestlers in history. However, as wrestling fans are well know, sports entertainment is about a whole lot more than any one individual contest. What happens between the wrestlers involved before and after their matches is equally if not even more important, and once again, Ric Flair excels above just about everyone else when it comes to engaging in epic rivalries against iconic performers. In addition to all the legendary athletes mentioned in the entry about his best matches, Flair also had fantastic feuds with names like Hulk Hogan, Vader, Dusty Rhodes, Lex Luger, and plenty of others during the territorial era that have now been forgotten to time. No one could ever forget Flair, though, and looking back on these programs, its hard to understand how it even happened to his opponents.

2 2. JUST GOOD: He Was As Political As The Rest Of Them

When it comes down to it, success in pro wrestling isn’t always related to talent, skill, or ability. Far more important than what happens inside the squared circle are the secret meetings occurring behind the scenes, with the most famous wrestlers in history usually achieving that status through no small amount of political maneuvering. For better or worse, this was yet another area where Flair excelled above most others, having spent much of his time on top of NWA and WCW because he refused to let anyone else do so. This practice got to its worst whenever Flair was given booking power, which he used to intentionally ruin the prospects of any rising stars that might surpass him. Sting, Steve Austin, and just about every other Horsemen could have been bigger stars faster had Flair stepped out of the spotlight or accepted a loss or two, but he rarely did so without prodding, making him imperfect, to say the least.

1 1. GREATEST: His Unmatched Gift Of Gab

Ultimately, the fact pro wrestling is scripted means superlatives such as “the greatest of all time” come down to a matter of opinion. Different people like alternating styles of sports entertainment, and few wrestlers have ever been so versatile as to make absolutely everyone happy from bell to bell, night to night. That said, there’s really only one type of trash talk, and one would be hard pressed to find a single soul who didn’t accept that Ric Flair was indeed the best of all time in this regard. No one could talk themselves up or tear the opponent to the ground like The Nature Boy, and he often did so in such hilarious fashion that announcers started laughing and fans cheered profusely even when he was the biggest heel in the business. When not trying to be funny, Flair has also exuded a passion like no other during his most heartfelt speeches, creating a true connection with his fans that has never faltered or dissipated in any way. So, where does this leave his legacy? Perhaps we could sum it up with another quote of his: like it or not, you better learn to love it, because it was the best thing going in its day.