49) Shane Douglas
50) Buddy Rogers
Towards the end of his active wresting career, Buddy Rogers feuded with Ric Flair in the Carolinas, both for bragging rights and each man's claim to the "Nature Boy" nickname. Flair defeated Rogers cleanly in 1978; one of Buddy's final matches before retiring from in-ring competition.
When Vince Russo and Eric Bischoff took over WCW in 2000, one of their goals was to build storylines based on reality. Shane Douglas had been dogging "Dick" Flair for years from the confines of ECW; when both men were in the company at the same time, a heated rivalry seemed to make sense.
Although this particular rivalry didn't last long, Flair was dogged by Warrior during his second WWF World Title run in 1992. The Ultimate One challenged Flair for the belt several times on the house show circuit and the two were poised to meet in a tag team match at Survivor Series when Warrior suddenly quit the company.
Flair clashed with the master of the Coco Butt early in his career, particularly in the Carolinas. Flair defeated Brazil to win his very first United States Championship back in 1977, setting the stage for a career where Naitch was covered in championship gold.
47) The Ultimate Warrior
48) Bobo Brazil
The third consecutive giant on our list and easily the most famous, Andre battled Ric in 1977 in the Carolinas in both singles and tag team matches. More famously, Flair has told stories about how, after their matches, Andre once consumed 105 beers in one sitting.... so perhaps there was a drinking rivalry as well?
One of Flair's most persistent challengers to his WCW World Title in 1991 was El Gigante, the 7"6 giant who could barely wrestle or speak English but looked quite impressive slamming Slick Ric to the ground. Believe it or not, there were rumors at the time that WCW VP Jim Herd was going to give Gigante the championship!
43) Andre The Giant
44) El Gigante
46) Chris Jericho
Although The Four Horsemen's feud with the nWo never really took center stage during the Monday Night Wars, it was always bubbling below the surface. During the rivalry, Hulk Hogan spray-painted a mohawk into Flair's head, Horseman Curt Hennig defected to the nWo and Syxx dressed like Naitch.
While serving as a traveling World Champion in the NWA, Flair visited Memphis several times and clashed with Lawler, including a match that drew record attendance at the Mid-South Coliseum in September 1985. These two also locked horns on Monday Night Raw some 19 years later.
Although there was also real-life heat between the two during Russo's WCW run, there was also an interesting on-screen rivalry in which Russo turned Flair's son David against him and conspired to shave Nature Boy's head following a match.
Although not as heralded as some of his other WCW rivalries, this began at Spring Stampede in 1999 when Page was the surprise winner of the WCW World Title in a four-way match featuring Flair. Later that year, a family feud emerged, with Ric and David Flair at odds with Diamond Dallas and Kimberly Page.
42) new World order
41) Jerry The King Lawler
40) Vince Russo
39) Diamond Dallas Page
In March 1991, Flair defended his NWA/WCW World Title at the WCW/New Japan Supershow against the IWGP Champion Fujinami. Fujinami won both belts according to NWA (but not WCW) rules. The complicated situation was settled at Super Brawl '91, when Flair defeated Fujinami by pinfall.
A locker room confrontation between then World Tag Team Champions Doom (Butch Reed and Ron Simmons) and Flair and fellow Horseman Arn Anderson led to a series of tag team and singles matches in late 1990. Barry Windham substituted for Flair in some of the feud's later matches.
Orton was portrayed as a family friend and tag team partner of Flair, even holding Ric's daughter Megan on national television. But when Harley Race placed a bounty on Flair's head, Orton (along with Dick Slater) were quick to shift allegiances, piledriving Flair and keeping him out of action for several months.
About two decades after feuding with his father, Flair embraced Randy Orton as the future World Champion in the Evolution faction. But by mid-2004, Flair (along with Triple H and Batista) decided to kick Orton out of the group, leading to a rivalry that was still apparent on television even a decade later on Raw.
38) Tatsumi Fujinami
37) Doom
36) Bob Orton Jr.
35) Randy Orton
When Flair returned to the WWF in late-2001, he was revealed to be the company's co-owner, which didn't sit well with his "partner" McMahon. This ignited a rivalry that included a match at the 2002 Royal Rumble and by late 2007, Mr. McMahon told Flair that he would have to retire from wrestling the next time he lost a match.
At The Great American Bash in 1989 (easily the best WCW PPV ever, by the way), Muta aligned himself with Terry Funk in an effort to put Flair out of action and take away his NWA World Title. Flair formed an uneasy alliance with Sting, and the four battled singles and tag matches until the end of that year.
A decade after the two first teamed in the WWF, Undertaker and Flair faced off against each other at WrestleMania X-8. Leading up to the match, The Dead Man attacked Flair's son David and injured his best friend Arn Anderson, leading to a classic grudge match.
34) Vince McMahon
33) The Great Muta
32) Steve Austin
31) The Undertaker
The Hit Man upset Flair in October 1992 to win his first (and Nature Boy's last) WWF World Championship in Saskatoon, Saskatchewan. The two crossed paths again when Hart joined WCW in late 1997 and even engaged in a memorable match at Souled Out the following year.
Foley was able to use a real-life incident, in which the two traded insults in their respective biographies, into an in-ring feud in the WWF in the summer of 2006, which led to a memorable "I Quit" match at SummerSlam. Four years later in TNA, the two hall of famers rekindled their rivalry briefly.
30) Arn Anderson
29) Black Jack Mulligan
28)Bret Hart
27) Mick Foley
Shortly after regaining the WCW World Title from Sting in 1991, The Nature Boy defended his belt against Steiner during a live Clash of the Champions event. It would be almost two decades later when Big Poppa Pump ripped into Flair on a live Nitro, making fun of his crooked teeth, banana nose and diminishing returns as an attraction, a move that led to bad blood backstage.
During the earliest incarnations of The Four Horsemen, Flair and his teammates could often be found looking across the ring at The Legion of Doom in singles, tag and trios matches. In fact, Flair defended his NWA World Title against both Hawk and Animal during various matches in the Great American Bash tour and clashed with Hawk at the Bunkhouse Stampede PPV.
The Russian Nightmare was set to face Flair for the NWA World Title at Starrcade '86 before an injury to Magnum T.A. altered everyones plans. Soon, Koloff challenged Flair throughout the country, including a cage match that truly made The Four Horsemen.
When Flair returned to WCW in 1993, Rude soon targeted The Nature Boy in the ultimate battle between ladies men. The Ravishing One defeated Flair for the NWA World Championship (a separate belt from the WCW one), leading to a split between the two groups.
Garvin's blue collar character was an excellent contrast to Flair's life of the party gimmick, and the two clashed in September 1987. Garvin surprisingly won the NWA World Championship from Flair and dropped it back a few months later at Starrcade.
Perfect started as Flair's executive consultant in the WWF, turning against Slick Ric in late-1992 and challenging him to as "Loser Leaves WWF" match in early 1993 (which Flair lost). Flair was betrayed again in WCW, when Hennig turned on Flair to join the nWo.
In the late-1970's, Ric and Wahoo traded the Mid-Atlantic Title back and forth several times while in Jim Crockett Promotions. At one point, The Dirtiest Player In The Game smashed McDaniel in the face with a broken table leg, legitimating injuring him because there was a piece of nail sticking out of the leg.
Things don't get much more personal than a son against his father, which is what happened (twice over a two-year period, mind you) in WCW. The first time David was seduced by Torrie Wilson into helping the nWo; the second time was when Vince Russo became a father figure to him as part of the New Blood storyline.
Funk was serving as a judge for a Flair-Rick Steamboat match in 1989. After congratulating Ric on a hard-fought victory, Funk piledrove him through a ringside table, igniting one of the more brutal rivalries in NWA history. The two feuded until the end of the year, at which time The Funker said he quit in the center of the ring.
One of Flair's all-time favorite opponents, he and Windham wrestled to several one-hour (and some 90-minute) draws in the summer of 1986. The rivalry ended when Windham was recruited to join The Four Horsemen, although the two men clashed again when Flair returned to WCW in 1993.
Perhaps an odd choice to placed so high on this list, but The Rated R Superstar ended up giving Flair some of his toughest moments towards the end of his in-ring career. Edge even spoofed Flair's road rage incident that happened during their rivalry, dressing up as his nemesis for a memorable vignette.
As one of the most popular wrestlers in Jim Crockett Promotions during the early 1980's, it was only a matter of time before Magnum crossed paths with The Nature Boy. The two feuded in Jim Crockett Promotions and may have gone longer had it not been for the car accident that ended Magnum's career.
After returning to WCW in 1993, Flair was placed in a WCW World Title match against Vader (a substitute for the fired Sid Vicious). Flair would have had to retire if he lost their Starrcade encounter, and the two had a brutal match in which Flair won the gold. They also battled in 1995 on a handful of pay-per-views.
Unlike with Vader, The Heartbreak Kid was able to enforce Flair's retirement stipulation in WWE after the two met in an all-time classic at WrestleMania 24. Although a mostly-scientific match, the bout was incredibly competitive throughout. Michaels mouthed that he was "sorry" before superkicking Nature Boy into retirement.
In 1986, The Four Horsemen became jealous of the cheers being heard by The Rock and Roll Express and set to end it. One day after Morton defeated Flair in a non-title match, the Horsement attacked him in a parking lot and broke his nose. This led to a series of matches between Flair and Morton that mostly ended in one-hour draws.
Flair was the only member of Evolution that hadn't defected against its leader Triple H, so it was surprising that when The Game returned to action in 2005, he immediately turned on Flair following a tag team match. The two former friends engaged in a brutal series of matches, including a steel cage bout.
Flair and Macho Man feuded not once, but twice, and in two different companies. Naitch lost his WWF World Title to Savage in 1992 in a match that included doctored photos of Miss Elizabeth, and Flair won the belt back later that year. They also traded the WCW World Title back and forth several years later.
Decades for they participated in Celebrity Wife Swap, Piper and Flair swapped the U.S. Title in Mid-Atlantic Wrestling in an early 1980's rivalry where each man tried to out-cheat the other. Things picked up in the WWF a decade later, with Piper disputing Flair's claim that he was The Real World's Champion.
If this were a list of Top 50 Real-Life Ric Flair Rivalries, this may very well be number one. But even as an in-ring storyline, this was a remarkable conflict with Bischoff trying to disband The Four Horsemen and fire Nature Boy from WCW. In 1999, Bischoff gave Flair a haircut after a match, adding insult to injury.
In June 1983, Race ended Flair's very first NWA World Title reign. Sensing that Flair would be a tough challenger, Race put up a $25,000 bounty for any wrestler who could put Nature Boy out of action, collected by Bob Orton and Dick Slater. Flair returned from injury and defeated Race at the first Starrcade.
Luger was one of Flair's most persistent challengers in the early 1990's. Nature Boy began as the babyface and later turned heel, while Luger took the opposite route, even challenging Flair on behalf of his friend Sting. Luger was also briefly a member of The Four Horsemen, which added fuel to the fire.
The storied Steamboat-Flair rivarly began in the early-1980's in the mid-Atlantic region, with Steamboat tearing Flair's clothes off of him on television. The two later engaged in a classic three-series match in 1989, trading the NWA World Title back and forth. They had one final big clash at WCW Spring Stampede in 1994.
Rhodes's Son Of A Plumber persona was the perfect foil for Flair's limousine-riding, Lear jet-flying persona. Flair defeated Rhodes for his first NWA World Title and they traded the belts back and forth from there in a memorable rivalry. During the dying days of WCW, the two ended up on opposite sides for one last chapter in their feud.
25) The Road Warriors
26) Scott Steiner
23) Rick Rude
24) Nikita Koloff
21) Mr. Perfect
22) Ron Garvin
19) David Flair
20) Wahoo McDaniel
17) Terry Funk
18) The Von Erichs
15) Barry Windham
16) Edge
13) Big Van Vader
14) Magnum T.A.
11) Ricky Morton
12) Shawn Michaels
9) Macho Man Randy Savage
10) Triple H
7) Eric Bischoff
8) Rowdy Roddy Piper
5) Lex Luger
6) Harley Race
4) Ricky Steamboat
3) Dusty Rhodes
Hogan and Flair - that phrase alone ushers in images of one of wrestling's biggest dream matches, as both men stood atop their respective companies in the 1980's. They first began feuding in 1991 in the WWF, carried it over to a series of pay-per-view grudge matches in WCW beginning in 1994 and even took their show on the road in Australia and briefly in TNA.
Arguably no one is linked as closely to Ric Flair's storied career as Sting, the icon who first clashed with Nature Boy at the first Clash of the Champions in 1988. They would go on and trade the WCW World Championship, team and feud with other several times and even took their rivalry to TNA. What's more, the two men tangled on the first - and last - episode of WCW Monday Nitro, demonstrating how long their rivalry lasted.
2) Hulk Hogan
1) Sting
A while back, we looked at some of Hulk Hogan's biggest rivalries over the years. But even The Hulkster hasn't carried as many grudges as The Nature Boy Ric Flair. Woooooooooooooo!
In compiling this week's Top 50 list, we looked at the biggest rivalries Flair has had over a career that began in 1972 and has seen action in the AWA, WCCW, NWA, WWF/E, WCW and TNA.... just to name a handful of the territories where Naitch has made his presence known.
To be clear, these are grudges that became apparent on camera and aren't necessarily tied to a backstage dispute (unless said dispute was later exploited on television). And as was the case with Hogan, the rivalries may not necessarily all be with wrestlers, per se, but could be with managers, valets, announcers and authority figures -- anyone who has ever crossed "The Man".
Ready? Here we go!
Related Posts: Top 50 Hulk Hogan Rivalries, Top 50 Regrettable WCW Characters
Any names missing or misplaced? Leave your feedback in the Comments section below...
This rivalry began in 1993 when Austin was Stunning Steve - he and Hollywood Blond partner Brian Pillman often targeted Flair and made fun of his age. It took a good nine years, but Naitch got his revenge in WWE, turning on Austin while acting as Raw GM.
Flair and Anderson are long-time friends and tag team partners. But in 1995, tired of almost coming to Flair's aid, The Enforcer split from his teammate in 1995 and faced off against each other in WCW. Soon, the two managed to put their differences aside.
While the two were friends outside the business (and even owned a territory together briefly), Flair and Black Jack feuded extensively in the Mid-Atlantic area in the late-1970's. Mulligan even went so far as to wear Flair's famous robe to the ring and tear it to shreds!
45) The Giant
Flair's Four Horsemen faction and Giant's Dungeon of Doom had a casual pact as allies until Giant challenged Flair in 1996 and captured his WCW World Heavyweight Championship. The two were later on opposite sides on occasion in WWE, when Giant became better known as The Big Show.
In 2002, Jericho appeared unexpectedly on Monday Night Raw (he had been on SmackDown at the time) and targeted Flair, leaving him laying in the center of the ring. Flair and Jericho then clashed at SummerSlam that year, with Jericho being the person to submit to Flair's figure-four-leglock in many years!
In 1983, the Missouri Champion David Von Erich was feuding with Flair over Ric's NWA World Championship, which gave Naitch an opportunity to rile up Mike Von Erich at the same time. By 1984, after David had passed away, Kerry Von Erich was the next in line, and managed to briefly capture Flair's World Title in Texas.