The wrestling world has rallied around the legendary “Nature Boy” Ric Flair this week as he has been hospitalized with a serious medical situation. For someone who has been retired for almost 10 years (yes, we’re ignoring anything involving TNA), it is amazing that Flair has still held such a relevant place in popular culture.

His synonymous “WOOOOO!” is heard in arenas and stadiums throughout the country. He’s also become somewhat of a motivational speaker, popping up in places like the University of Michigan and PGA Championship promos. And a 30 for 30 chronicling the highs and lows of life in and out of the ring will be debuting on ESPN later this year.

Flair is at the very top of the conversation for most fans when they consider who is the best professional wrestler of all time. And though it’s Flair’s famous promos about limousine-riding, jet-flying lifestyle that are most remembered, let’s take time to look back at what has made Flair stand the test of time: his best matches.

For a man who has had thousands of matches, this list can be made 100 times over with any number of bouts. To record every meaningful or fun or famous match of Flair’s storied career would take days. So here, especially for fans who may not be as familiar with the Nature Boy’s work in the ring, is a purely subjective list of a dozen matches to start with that are must-see to capture what made Ric Flair “The Man.”

12. Starrcade 1983

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

Although Flair had been world champion once before, this was undoubtedly the match that established him as one of the biggest stars in wrestling. Race was a multiple-time world champion, much rarer in those days, and the new Starrcade event had been entirely built around Flair recapturing the title. In fact, the event had the subtitle, “A Flair for the Gold.”

In effect, the match passed the torch of the NWA from Race to Flair as the standard bearer. And while it’s tough for anything to hold up as well over a period of almost 25 years, the intensity of the match is still palpable today, even if nobody is diving off of ladders or falling off the top of the cage. The match does get dragged down, though, by a bizarre performance from guest referee and legendary wrestler Gene Kiniski.

What To Look For: How things change in a quarter of a century. While blood is a rarity in wrestling today, it was spilled liberally in the 80s. The aerial shots of the blood-stained mat are truly eye-opening, not just from the main event, but from the infamous Dog Collar Match earlier in the night between Roddy Piper and Greg Valentine.

11. Halloween Havoc 1989

ThunderDome Cage Match
Ric Flair & Sting w/Ole Anderson vs. The Great Muta & Terry Funk w/Gary Hart

The second match on the list is probably the most obscure, and is not the typical five-star technical masterpiece hardcore fans associate with Flair. Maybe it’s the fact that the match features two other of yours truly’s favorite performers (Muta and Funk). But this match has continued to stick with me throughout the years. The most interesting fact about the match is that it can be thought of as a forerunner to Hell in a Cell, as for one of the first times, a regular cage wasn’t enough.

This match featured a domed cage that had the added feature of being electrified! Further, the match could only be won if the opposition’s manager threw in the towel. While you could also watch any of the original War Games matches featuring The Four Horseman vs. Dusty Rhodes and friends, this match is a better showcase for Flair as he teamed with long-time rival Sting to take on Muta and Funk in a high-energy spectacle.

What To Look For: Special guest referee and WWE legend Bruno Sammartino makes a rare appearance, and also plays a key role in the match’s finish!

10. Wrestlemania X-8

No DQ Match
Ric Flair vs. Undertaker

After the purchase of WCW by Vince McMahon and WWE, many of the top stars of the former brand were left in limbo. You won’t find any matches on this list from the final days of WCW, and perhaps to the surprise of many, Flair’s arrival in WWE reinvigorated his in-ring career. Originally, Flair was brought in as an on-screen authority figure. However, in Flair’s first WrestleMania match in 10 years, he showed he still had plenty left in the tank as he went toe-to-toe with the Undertaker in a memorable brawl.

While the event itself is more remembered for the confrontation between Hulk Hogan and The Rock, this match holds up just as well, looking back. More importantly, it showed that Flair could still go in his second stint with WWE.

What To Look For: The best part of the match is Arn Anderson with one of the all-time great run-ins to deliver his trademark spinebuster.

9. Clash of the Champions IV

Tag Team Match
Ric Flair & Barry Windham w/J.J. Dillon vs. The Midnight Express w/Jim Cornette

Clash IV is like looking back on the late 80s through bizarro lenses. The Road Warriors were turned heel to go up against Dusty Rhodes while The Midnight Express, despite being villains for much of the decade, were cheered as heroes going against The Four Horsemen. Seeing Jim Cornette introduced to thunderous applause before the match was strangely unsettling. Still, this hidden gem is an absolute classic from bell-to-bell. Flair is on fire from the start, bumping like crazy for both Bobby Eaton and Stan Lane.

In fact, looking back, one of Flair’s greatest qualities was elevating whoever he was in the ring with at the time. Whether it was singles matches with the likes of Scott Steiner or Ricky Morton, or tag team matches against a variety of opponents, Flair brought the best out of everyone. Being teamed with Windham, one of the top in-ring performers of the time, led to a pulsating back and forth encounter that could only end through the use of a foreign object.

What To Look For: Look here for a cameo during the match from a young Paul Heyman, then Paul E. Dangerously, as he hypes an upcoming encounter between his “original” Midnight Express and Cornette’s Midnight Express.

8. WrestleMania XXIV

Career Threatening Match
Ric Flair vs. Shawn Michaels

Amazingly, as of 2008, Ric Flair was still an active wrestler. And though I wasn’t into the product at the time, the story of Ric Flair’s career hanging in the balance was enough to begin pulling me back. The next time Flair would lose a match, it would be the end of his career. In the leadup to WrestleMania, Flair went on a surprise winning streak. If his career were to continue, though, he would have to defeat his close friend: Mr. WrestleMania, Shawn Michaels. Even though Flair was approaching 60 years of age, the two had a classic encounter that was the height of in-ring storytelling.

Who could forget Michaels mouthing “I love you” before the final curtain fell on Flair’s in-ring career. It was the perfect ending to a storied career –again, as long as we’re all agreed we’re ignoring that whole TNA thing.

What To Look For: So many little details. For long-time fans of Flair, there were several call backs to trademark Flair spots, with just a little twist to keep everyone on the edge of their seats. The referee is Charles Robinson, dubbed “Little Naitch,” and future WWE Women’s Champion Charlotte (Flair’s daughter) also appears on screen.

7. Clash of the Champions I

NWA World Heavyweight Championship Match
Ric Flair (c) vs. Sting

The inaugural Clash was conceived as a way for Jim Crockett to go head-to-head with WWF’s WrestleMania IV by airing a free wrestling special on TBS. The main event would naturally feature world champion Ric Flair, but his opponent was a young upstart, Sting. The 45-minute time limit draw would be the match that put Sting on the map. Although it would take a few more years for Sting to climb the top of the mountain, this match kickstarted a rivalry that would last all the way to the final episode of WCW Monday Nitro in 2001.

Again, this is Flair at the top of his game, showing all the tricks of the trade that led him to be dubbed “The Dirtiest Player in the Game.” The final few minutes that led to the time limit built tension and drama right to the final bell. Although, the draw itself was gimmicked through the use of “celebrity” judges, who still couldn’t separate the new rivals.

What To Look For: Flair’s manager J.J. Dillon had the best view, suspended high above the ring in a cage. Also, strangely enough, only 3 of the 5 judges scores were revealed at the end of the bout.

6. WrestleMania VIII

WWF World Heavyweight Championship
Ric Flair (c) w/Mr. Perfect vs. Macho Man Randy Savage

In the annals of WrestleMania, this match remains severely underrated as a true classic of the Super Bowl of wrestling. Perhaps it has to do with the match taking place in the middle of the card, instead of the true main event. Instead, that honor went to Hulk Hogan and Sid Justice in one of the worst WrestleMania main events of all time. Also, some hardcore fans look back at WM 8 as a missed opportunity for the dream match between the biggest stars of their respective promotions, Flair and Hogan.

Still, Flair and Savage certainly delivered the goods, much like they did throughout their rivalry spanning both WWF and WCW. Certainly, this was the most high-profile encounter the two would share. Adding to the personal issues between the two were Flair’s claims about Savage’s wife and former manager, Miss Elizabeth. The match itself mixed Flair’s technical prowess with his brawling best to match the unbridled intensity of the Macho Man in a fun encounter.

What To Look For: As Miss Elizabeth makes her way to ringside during the match, look for one of the officials trying in vain to stop her — a baby-faced Shane McMahon.

5. Clash of the Champions VI

2 Out of 3 Falls Match for the NWA World Heavyweight Championship
Ric Flair vs. Ricky Steamboat (c)

The second match of Flair’s famous trilogy with Ricky “The Dragon” Steamboat begins our Top 5 and was certainly the most physically grueling of the three encounters. Clocking in at just short of an hour, Flair and Steamboat showcased the chemistry and physical conditioning that separated them from their fellow competitors. While Flair had storied rivalries with others like Dusty Rhodes, Lex Luger, Barry Windham, Sting, Hulk Hogan, etc., it is his series of matches with Steamboat that most wrestling aficionados point to as the height of the industry.

Matches like these take pro wrestling from sports entertainment to something closer to performance art. And the controversial finish brought about the third and final match in the trilogy. (More on that later.)

What To Look For: The event was held in the Louisiana SuperDome, formerly a hotbed of territories like Mid-South Wrestling. However, even though 1989 may have been Flair’s best year in the ring, only 5,300 fans filled the massive dome for the event. Even worse for Naitch, he was introduced as “Rick Flair” in his fancy pyro graphic.

4. Starrcade 1993

WCW World Heavyweight Championship Match
Ric Flair vs. Big Van Vader (c) w/Harley Race

In 1993, Ric Flair had returned home to WCW from his brief time with WWF. That year’s Starrcade featured several storylines coming to a head. If Flair challenging the monster Vader wasn’t enough, the event was also taking place in Flair’s adopted hometown of Charlotte, North Carolina. The match was also built as a retirement match for Flair if he lost to the champion.

The contest again displayed how incredibly tough Flair was as he took an insane beating from Vader, but continued coming back for more, dishing out as much punishment as he took. While Flair is probably more well-remembered for his bad guy persona, here he played the hometown hero role as well as could be done. Add to that an insane crowd and a flash finish and you get one of Flair’s most memorable championship victories.

What To Watch For: Another factor that added to the match was the additional synergy of Flair’s opponent being managed by his foe at the original Starrcade 10 years earlier, Harley Race, who of course gets involved early and often.

3. Clash of the Champions IX

I Quit Match
Ric Flair vs. Terry Funk w/Gary Hart

Another match from 1989, this encounter was the blowoff for the bitter feud between Flair and Funk. Of course, a regular match wouldn’t suit such an occasion, so the stipulation was added to make the bout an I Quit Match, where the winner would be the competitor who made his opponent utter the humiliating phrase.

Though the match is less than 20 minutes, it packs action that was rare for the time, like tables, chairs, and microphones used as weapons. Again, another example of Flair being one of the greatest because of his versatility in the ring, equally adept at technical masterpieces and back alley brawls.

What To Watch For: 1989 isn’t only peak Ric Flair, but it’s peak Jim Ross. Before he became Good Ol’ JR, Ross called the action as an intense sporting competition, which only added to the tension and drama –a far cry from today’s WWE announcing philosophy.

2. WrestleWar 1989

NWA World Heavyweight Championship Match
Ric Flair vs. Ricky Steamboat (c)

This match is the culmination of Flair’s famous trilogy with Steamboat and is widely considered one of the greatest contests of all time. There are no crazy spots or gimmicks to draw the audience in artificially, just wrestling at its purest. Flair finally got his victory over Steamboat, reclaiming the World Championship, and firmly becoming a fan favorite in the process.

The greatest compliment the match can receive, is that words don’t do it justice, just play the entire video as soon as you’re done reading this article.

What To Watch For: Stay for the post-match interview where judge Terry Funk crashes the party, kicking off his feud with the Nature Boy featured above by giving him a piledriver on a table. Even back in 1989, Funk was as crazy and as hardcore as they come.

1. Royal Rumble 1992

WWF World Heavyweight Championship Match
Ric Flair vs. 29 other men

The greatest Royal Rumble of all time, the greatest announcing act of all-time, and the greatest performance in Ric Flair’s career. The WWF title was vacated due to a controversy involving the “Real World’s Champion,” so the Royal Rumble would be used to crown a new, undisputed champion. Few would have given Flair a chance when he entered No. 3 out of 30. But by lasting over an hour, Flair outlasted over a dozen current or future Hall of Famers to win the WWF Championship for the first time.

And it’s not as if Flair just sat in a corner for an hour. Almost every single wrestler that entered the match interacted in some meaningful way with Flair. Some of the greatest names of the classic era like Hogan, Savage, Piper, Michaels, Roberts, etc. are all instrumental in crafting one of the great matches in WWF history. The combination of Flair’s skill and endurance, the sublime commentary of Gorilla Monsoon and Bobby Heenan, and the most star-studded Rumble in history makes this match above all others stand out in the storied career of Ric Flair.

What To Watch For: As great as the match itself was, Flair gave perhaps one of his greatest promos ever after his victory. With a tear in my eye!

About Matt Yoder

Award winning sportswriter at The Comeback and Awful Announcing. The biggest cat in the whole wide world.