Ric Flair’s Greatest Wrestling Matches of All Time

In the 1980s, two figures dominated the landscape of pro wrestling: Hulk Hogan in the WWF, and Ric Flair in the NWA. Whereas Hogan made a career out of his larger-than-life presence and family-friendly personality, “Nature Boy” Ric Flair established himself as a roguish heel willing to do whatever it took to win.

The most athletic performer of his era, Flair demonstrated the inherent physicality and stamina it took to become a pro wrestler, as seen with his various lengthy matches against Ricky Steamboat, Sting, and Randy Savage. A legendary talent for the NWA, WWF, and WCW, Flair won audiences’ favor with his energetic promos, flamboyant ring attire, and his open willingness to cheat whenever the referees had their backs turned (earning him the fitting nickname, “The Dirtiest Player in the Game”).

A legend in the industry whose career spans a whopping five decades, Flair’s career is filled with aspirational heights and personal lows, including several world title reigns and prestigious matches against everyone from Hulk Hogan to Shawn Michaels. From his earliest championship victories against Harley Race and Dusty Rhodes to his iconic match-ups against Ricky Steamboat, check out some of the greatest matches to feature Ric Flair in action, ranked from best to worst.

Ric Flair vs. Ricky Steamboat (Chi-Town Rumble)

Ric Flair’s single greatest opponent will always be Ricky Steamboat. Ideal rivals in terms of their pure athleticism, Flair and Steamboat mirrored each other not only in their training and background but also in their rise to prominence. Competing against one another in numerous matches from the late 1980s into the mid-1990s, Flair and Steamboat's best match came at 1989’s Chi-Town Rumble.

The first of several fantastic matches between the Nature Boy and the Dragon, Chi-Town Rumble demonstrated the unique chemistry Flair and Steamboat possessed whenever they crossed paths in the ring. With Steamboat flying off the ropes and Flair using every illegal move he could think of to gain an edge on his opponent, the two proved evenly matched in their abundant resourcefulness and expert stamina. Though unable to prevent Steamboat from claiming his NWA World Heavyweight Championship, Flair nevertheless kicked off an iconic feud between his legendary nemesis.

Ric Flair vs. Ricky Steamboat (WrestleWar ‘89: Music City Showdown)

The epic final bout that ended Steamboat and Flair’s trilogy of classic matches, the Dragon and the Nature Boy squared off in a lauded rematch at WrestleWar. Having lost to Steamboat at Chi-Town Rumble and Clash of the Champions VI, Flair pulled out all the stops when it came to this climactic match, desperately trying to recapture his NWA World Heavyweight Championship.

As with their two earlier classic bouts, WrestleWar ‘89’s showdown between Flair and Steamboat ended up being as historic a battle as their earlier matches. Putting aside his traditional cocky attitude, a far more methodical Flair doubled down on his pure wrestling ability, packing a ton of power into each knife-edged chop. Though Steamboat made a valiant effort to curb Flair’s momentum, a timely roll-up on the Nature Boy’s part helped Flair secure a hard-earned victory over his famed opponent.

Ric Flair vs. Terry Funk (Clash of the Champions IX)

If Flair illustrated his deft wrestling talent against Ricky Steamboat throughout 1989, his “I Quit” match against Terry Funk at Clash of Champions IX demonstrated his ability to engage in more violent matches. Facing the street-fighting Funk in a hyper-violent grudge match at Clash of Champions, the two beat each other to a pulp, relying more on Funk’s background than Flair’s technical wrestling know-how.

Brawling down the entrance ramp moments after the match started, Funk and Flair took turns chopping each other full-force across the chest for a punishing 18 minutes. A precursor to the “strong style” wrestling later adopted by NJPW, Funk and Flair’s match here made for one of the most unique, exciting, and violent matches in WCW’s history – one well ahead of its time.

Ric Flair vs. Ricky Steamboat (Clash of the Champions VI)

While one upset victory might seem like a fluke, Ricky Steamboat proved the naysayers wrong when it came to his title rematch at Clash of the Champions VI. Squaring up against the Nature Boy in a two-out-three falls match for the NWA World Heavyweight Championship, Steamboat showed the world that he had what it took to become the face of the NWA, beating Flair two falls to one (albeit in controversial fashion).

Opening the bout with a traditional collar-and-elbow tie-up, Flair and Steamboat went head to head in a battle of strength and speed, taking turns locking each other in taut submission holds and systematically singling out each other’s weakened legs. Trading vicious blows and thunderous chops, Steamboat soon caught Flair in a devastating double chicken wing submission. Although an exhausted Flair reversed the hold and placed his foot on the ropes, the referee failed to notice, counting a one-two-three victory in favor of Steamboat.

Ric Flair vs. Sting (Clash of the Champions I)

Like his frequent clashes with Ricky Steamboat, Ric Flair found a recurring thorn in his side with up-and-coming NWA talent, Sting – a man who challenged Flair time and time again from the late ‘80s to the early 2010s. As epic as their later rematches were, the opening chapter in Flair and Sting’s rivalry came at the inaugural 1988 Clash of the Champions.

Competing for Flair’s World Heavyweight Championship, the Nature Boy and the Stinger fought for a hair-raising 45 minutes, ending in a disappointing time-limit draw. Despite its disappointing conclusion, however, Flair and Sting conducted an otherwise classic wrestling bout. As the first legitimate threat Flair had faced in some time, Sting – though unsuccessful in winning the world title – came out of the bout looking like a future champion in the making, using his strength, stamina, and never-say-die attitude to keep up with Flair throughout.

Ric Flair vs. Dusty Rhodes (The Great American Bash 1986)

Though Flair had undeniable chemistry against most performers he worked with, one of his most memorable rivalries came against “The American Dream” Dusty Rhodes. A man Flair had once idolized upon his entry into pro wrestling, and Flair had managed to supersede Rhodes by the early ‘80s, taking Dusty’s place as the key figurehead of NWA. As their rivalry became more and more personal, the two men decided to settle their differences in an embittered grudge match at 1986’s The Great American Bash.

Fighting inside the imposing steel cage, Rhodes and Flair’s colorful personalities and in-ring abilities made them natural foes. With Rhodes embodying the blue-collar everyman character audiences could relate to and cheer for, Flair hammed it up as the over-the-top, luxury-loving millionaire. Like his earlier 1983 cage match against Harley Race, the resulting bout ended up being physical and and rife with emotion, concluding with Rhodes reclaiming the world title from Flair in a shocking finish.

Ric Flair vs. Sting (The Great American Bash 1990)

Wrestling history has its fair share of cathartic moments, often seeing the older generation passing the torch down to their successors. Just as Harley Race had ceded his place to Ric Flair at Starrcade ‘83, Flair bowed down to fledging upstart Sting, allowing the Stinger to win his first NWA World Heavyweight Championship at the 1990 Great American Bash.

A benchmark moment in Sting’s wrestling career, The Great American Bash made for an ideal follow-up to Flair and Sting’s earlier, indecisive encounter at Clash of the Champions two years prior. Enlivened by the constant cheering of the crowd, Sting relied on his buoyant energy to combat Flair’s constant offense, withstanding a non-stop barrage of Flair’s signature knife-edged chops. With his abundant liveliness in his reserve, not even the outside interference from Flair’s Horsemen distracted Sting long enough to turn the tide of the match, with Sting countering Flair’s figure-four into an emotional three-count.

Ric Flair vs. Shawn Michaels (WrestleMania XXIV)

At the tail end of 2007, a vindictive Vince McMahon issued Ric Flair an ultimatum: the next match Flair lost, he'd be forced to retire from in-ring competition. True to the Nature Boy’s resilient and rebellious nature, Flair went on to win every singles match he competed in for the next several months. Entering 2008’s WrestleMania XXIV, however, Flair went up against his most formidable competitor yet in the form of the Heartbreak Kid, Shawn Michaels.

A recurring ally/occasional rival for Flair, Michaels’ past history with the Nature Boy and his high-performance rate at WrestleMania made him a logical choice for Flair’s final match in WWE. Though slowed by age (he was 59 years old at the time of this match), Flair still gave it his all in this now-classic WrestleMania encounter, ending his lengthy tenure for McMahon’s promotion in the best (and most emotional) way possible.

Ric Flair vs. Harley Race (Starrcade ‘83: A Flare for the Gold)

In the mid-1980s, the wrestling industry experienced its Renaissance period, the golden age of legends like “Superstar” Billy Graham, Bob Backlund, and Harley Race drawing to a close. Before passing the torch down to the younger generation, however, reigning World Heavyweight Champion Harley Race did all he could to hold onto his prominent place in the NWA. Placing a $25,000 bounty on Ric Flair’s head when the latter made his intentions to win the world title clear, the two set up an epic match at the first-ever Starrcade.

Battling inside the steel cage on the day of the event, Race managed to establish Flair as a legitimate star in NWA, both men beating each other into a scarlet mess. Perhaps the most violent match Flair ever participated in (next to his “I Quit” match against Terry Funk, anyway), his victory over Race served as another major milestone in his career, with audiences around the world knowing the name “Ric Flair” by the end of the night.

Ric Flair vs. “Macho Man” Randy Savage (The Great American Bash 1995)

In 1994, prominent WWE superstar “Macho Man” Randy Savage departed Vince McMahon’s company for the greener pastures of WCW. Upon his arrival to this new promotion, Savage came across his former WrestleMania VIII rival, Ric Flair, competing against his old adversary in a series of matches throughout the summer of 1995.

This rivalry came to a head at WCW’s 1995 Great American Bash, which saw both men eliminated from a United States Heavyweight Championship tournament after a scripted backstage altercation. Freed from the tournament, the two veterans engaged in a fierce brawl in the pay-per-view main event. Making up for his loss at WrestleMania VIII, Flair’s dubious in-ring strategy managed to best Savage, with Flair stealing the cane of Savage’s father at ringside to thump the Macho Man in the head, scoring a pinfall victory over Savage in the process.

Ric Flair vs. Barry Windham (World Wide Wrestling)

Before he turned heel and became a prominent member of the Four Horsemen, Barry Windham eked out a name for himself as the son of Blackjack Mulligan. Living up to his elite wrestling pedigree, Windham fought against Flair multiple times from early 1986 into late 1987, the greatest of their matches occurring on the January 20 edition of World Wide Wrestling.

An explosive wrestling match filled with strikes, chops, and well-placed offensive moves instead of Flair’s traditional mat-based wrestling, Windham and Flair managed to go toe-to-toe when it came to sheer brutality and clubbing blows. With Windham landing a rapid-fire succession of clotheslines, strikes, and chops on Flair, the Nature Boy did what he could to reorient the match around his signature grappling style. Though unsuccessful in pinning the champ before the time-limit draw, Windham enthralled audiences with his aggressive offensive attacks, helping the young star cement his place in NWA at the time.

The Four Horsemen vs. Sting, Brian Pillman, and The Steiner Brothers (WrestleWar ‘91)

There’s no shortage of fantastic WarGames matches, whether vintage WCW bouts featuring the Four Horsemen or more recent NXT matches featuring The Undisputed Era, Kevin Owens, or The Bloodline. When looking back to WarGames’ earliest days, though, it’s hard to find a better match than WrestleWar ‘91’s main event brawl between the Four Horsemen and Sting, Brian Pillman, and the Steiner Brothers.

As anarchic a bout as any in WarGames’ history, WrestleWar ‘91 came loaded with unpredictable moments, all of which helped sell the unpredictable and unforgiving nature of the WarGames structure. With Flyin’ Brian taking a vicious beating throughout, Flair’s Horsemen took special care to single out Pillman for punishment. After two brutal-looking botched powerbombs from Sid Vicious (one of which dropped Pillman flat on his head), a concerned El Gigante forfeited the match on his friend’s behalf, the triumphant Horsemen standing tall in the center of the ring.

Ric Flair vs. “Macho Man” Randy Savage (WrestleMania VIII)

Flair and “Macho Man” Randy Savage’s first encounter came at WrestleMania VIII. Winning the WWF Championship at the 1992 Royal Rumble, the Nature Boy faced a worthy WrestleMania opponent with the Macho Man, leading to one of the best matches in Flair’s WWE career.

Exploiting Savage’s infamously short fuse regarding his valet, Miss Elizabeth (whom Flair hinted at having an affair with), Flair got inside Savage’s head and played his effective mind games against the Macho Man. Unfortunately for Flair, the psychological intimidation only went so far, with Savage performing a well-timed roll-up to win the WWF Championship to the electric applause of the crowd and a jubilant Miss Elizabeth.

Ric Flair vs. Lex Luger (Starrcade ‘88: True Gritt)

In addition to the slew of older veterans he beat on his way to the top (like Harley Race, Buddy Rogers, and Dusty Rhodes), Flair also defended his title against a wide range of rising performers in NWA, including Sting, Kerry Von Erich, and “The Total Package” Lex Luger. Initially aligning himself with the Four Horsemen, Luger struck out on his own in late 1987. Feuding with the Horsemen into 1988, Luger eventually turned his attention to capturing Flair’s world title, ending his rivalry against the faction for good.

Battling in the main event of The Great American Bash, Flair and Luger stood against one another yet again at Starrcade ‘88. In perhaps the best match of Luger’s career, the Total Package did his best to overwhelm Flair’s offensive style, using his height advantage, strength, and an occasional high-flying maneuver to lay the Nature Boy out. Just when it seemed Luger might win his his first world championship, a momentary slip-up on Luger's part allowed Flair to pin the challenger – with Flair using the ropes for leverage, as per usual.

Ric Flair vs. Vader (Starrcade ‘93: 10th Anniversary)

Making a name for himself in NJPW by the late 1980s, Vader arrived in WCW in 1990 and immediately left his impression. Landing in WCW with the same ferocity as Brock Lesnar in the 2010s, Vader waylaid every single opponent he stepped into the ring with, breaking several of Sting’s ribs and concussing Cactus Jack in some of his earliest bouts. Aided by Harley Race, Vader secured the World Heavyweight Championship at the 1992 Great American Bash, holding the title for nine months until losing it to Ric Flair at Starrcade ‘93.

A rare bout that saw Flair portraying a face, Flair’s match against Vader also served as one of the Nature Boy’s most remarkable matches in the latter half of his career. Contending with his most physically formidable opponent yet, Flair whipped out every trick imaginable in his brawl against Vader. After a momentary distraction from Race, though, Flair did the unthinkable, rolling up with the Mastodon for a surprise victory, earning him his second world title in WCW.