The first time the Ric Flair and The Undertaker characters crossed paths was in 1991 when Ric Flair helped The Undertaker defeat Hulk Hogan for the WWF Championship. It wasn’t until Ric Flair would return to the WWE in 2001 that they would cross paths again. Ric Flair returned as the “Co-Owner” of the WWE but found himself involved in Big Evil’s business. Ric Flair would refuse to face the Deadman until he was forced to accept the WrestleMania X-8 challenge after his family and friends were attacked.

The reason this feud made this list over feuds such as the ones with Triple H or Shawn Michaels was because of the significance it had on Flair’s self-esteem during this pivotal time of his career. Flair felt like he had lost confidence in himself as a performer and star in his final years in WCW, but The Undertaker requested to work with him for Wrestlemania to remind him who he was. That alone makes The Undertaker one of Ric Flair’s greatest rivals, although their feud was short.

Ric Flair was the World Champion, the top heel, and self-proclaimed lady’s man that actually could back it back. When the Rock ‘n’ Roll Express showed up in Jim Crockett Promotions, they were immediate fan favorites. The women in the crowd seemed to be especially fond of them and even more towards Ricky Morton.

In fear that his sex appeal was being threatened, the Nature Boy began a feud with Morton in the Spring of 1986. Flair would refer to Morton’s female fans as teeny boppers and claim he couldn’t handle grown adult women. They would have a series of matches and it would cap off in a Cage Match for the World Championship at the Great American Bash. However, Flair’s running mates of the Four Horsemen Arn and Ole Anderson would continue to terrorize Morton and Gibson for the rest of the year. You won’t be able to comprehend why this rivalry made this list unless you knew just how over Morton was in 1986.

It was a rivalry where art imitated what was happening in real life. Ric Flair didn’t always get along with WCW management going all the way back to the early 1990s and his disagreements with Jim Herd. It led to the Nature Boy leaving the brand he had been loyal to all throughout the 80s to join the rival WWE. By 1993 when Ric Flair returned to WCW, Eric Bischoff who was just an on-screen announcer for the company when Flair left was promoted in the company as the new head honcho in charge. Initially, the two got along well to the extent that Flair was pivotal in helping Bischoff in his pursuit to sign Hulk Hogan to WCW in 1994.

The relationship between the two soured in 1998 when Eric Bischoff filed a lawsuit against Flair for no-showing a Thunder taping in April. Flair has claimed he had asked for the time off ahead of time to attend his son Reid’s amateur wrestling tournament which Bischoff has no recollection of. This only added to Flair’s concerns that Bischoff wanted him out of the company as he felt like his role was diminishing in WCW as new main event stars would get signed. When the lawsuit was settled in the fall of 1998, Flair would return and immediately feud with Bischoff playing off of their real-life backstage drama. It would lead to some of the most memorable promos and segments from both men.

Although their on-screen rivalry concluded by the end of 1998, their real-life rivalry had one last physical altercation backstage at a Raw in 2002 when Flair attacked Bischoff. Wild. This years-long beef is definitely one of the best Ric Flair rivalries.

Ric Flair and “Rowdy” Roddy Piper have had their careers tied to each other longer than younger fans may know. Piper’s role in boosting the popularity of Hulk Hogan is very well documented by the WWE but the influence he had on Ric Flair’s career isn’t talked about a lot. They have been friends and they have been rivals, but they always had great chemistry.

First crossing paths in the early 1980s in Mid-Atlantic Championship Wrestling, they would cut scathing promos on each other and wrestle for the US Championship regularly before Flair was elevated as the top babyface to feud Harley Race for the World Championship. A lot of people believe he wouldn’t have gotten to that spot without his feud with Piper. They would have wrestled somewhere around 40 times all around the territories from 1980-1983 switching face/heel roles yet always keeping the same level of intensity.

The two would feud again in the WWE in the early 90s, have an off-and-on friendship in WCW during the last half of the 90s, and reunite multiple times in the WWE in the 2000s. They even won the tag team titles in 2006.

Depending on what you grew up on in the 80s, there will always be a debate about who the greatest wrestler of all time is between Ric Flair and Hulk Hogan. If you grew up on JCP/WCW, Ric Flair was your guy even though for the most part he was the cocky, arrogant, and self-absorbed bad guy. If you grew up in the WWF, then there was no force stronger than Hulkamania, which was led by the “say your prayers and eat your vitamins” hero known as Hulk Hogan. It was always a question of who would win if Ric Flair and Hulk Hogan crossed paths. It was a blockbuster match that could headline anywhere in the world.

Therefore, when Ric Flair showed up in the WWF in 1991 after leaving WCW due to disagreements with the new management, people salivated at the idea that we could finally get Hogan versus Flair. They even teased the mega-match all the way until a little after the 1992 Royal Rumble. They did have a ton of non-televised matches but never a major televised singles match before Flair went back to WCW. In 1994, Hogan would join WCW and his first big match would be against Flair at Bash at the Beach. They would continue to feud in WCW off and on till the year 2000.

They would reignite their feud in the WWE again, finally wrestling on Raw in 2002 for the Undisputed Title. In 2009, Flair wrestled Hogan even more times for the Hulkamania Tour in Australia. Their careers continue to cross paths to this day and fans still debate who was more important to the business.

The “Macho Man” Randy Savage is a six-time World Champion. He only ever lost the championship against two different men, Hulk Hogan and Ric Flair. He also beat Ric Flair for the World Title on two occasions. If you really think about someone the Nature Boy worked with a lot during the 90s, Macho Man has to be in the top five of that list. Both men were colorful, flamboyant, cocky, memorable promos, talented in the ring, and strived to be the best match on any card they were on. Their angles were always personal and usually involved Miss Elizabeth which always added an extra layer of drama.

It all started when the plans changed for Wrestlemania 8 and Randy Savage was now going to face the Dirtiest Player in the Game for the WWE Championship at the event. Ric Flair started to claim that he had a prior relationship with Savage’s then-wife Miss Elizabeth. He even doctored up photoshopped pictures of him sharing intimate moments with Elizabeth which drove Macho Man mad. They were no longer just fighting for the championship but for the honor of Savage’s wife and relationship. Randy Savage would defeat Ric Flair at Wrestlemania and later reveal the actual pictures which had himself in them. The feud would continue in the WWE until the end of 1992.

Their rivalry would reignite at Uncensored 1995 where Flair attacked Savage. Things would get personal again as the feud would involve Savage’s father Angelo Poffo and Miss Elizabeth again. Nobody really got under Savage’s skin better than Flair.

The Ricky Steamboat and Ric Flair feud goes all the way back to 1977 when Steamboat first joined Jim Crockett Promotions. Steamboat immediately was the ultimate babyface and Flair was his perfect counterpart. They both elevated each other in their rivalry in their early years. Steamboat had his first star-making victory against Flair when he won the Mid-Atlantic Television Championship. The feud between them got personal with Flair trying to scar Ricky’s face and Ricky destroying Flair’s expensive suits. Although the early rivalry was great, most people remember the trilogy of 1989.

Ricky Steamboat returned to JCP/WCW in 1989 after five years in the WWE. The idea to revisit his feud with Ric Flair was inevitable due to their chemistry and great battles in the past. Steamboat quickly became the number one contender for Ric Flair’s World Championship. Steamboat would defeat Flair at the Chi-Town Rumble to win the championship in a terrific encounter. They had a two-out-of-three falls rematch at Clash of Champions VI two months later which was another great match but ended in a controversial fashion. This led to them having a third match at WrestleWar 89’ where Ric Flair finally was able to regain the World Title. All three matches are highly praised.

They briefly feuded again in 1994 over the World Championship but Steamboat always brought the best out of Flair.

Harley Race was a tough, rigged, and well-respected veteran in the wrestling business who started his career in 1959. Race wrestled all around the territories as the National Wrestling Alliance’s World Champion. He had classic bouts with Dory Funk Jr, Jack Briscoe, Angelo Poffo, Pat Patterson, Giant Baba, Terry Funk, Dusty Rhodes, Billy Graham, Bob Backlund, Nick Bockwinkel, and many others. He had bloody affairs with the Sheik and even slammed Andre the Giant in 1978. Race was already a six-time World Champion by the time Ric Flair started pursuing the championship as the hot newcomer on the scene.

Race had lost the World Championship to his long-time rival Dusty Rhodes in 1981. Rhodes would lose the championship to Flair later that same year. Harley Race would defeat Naitch in 1983 for a seventh reign and it led to one of the greatest rivalries in the 1980s. Harley Race was so against defending the championship against Flair again, that he put a $25,000 bounty out on Flair for anyone who was able to injure him and eliminate him from the NWA. Bob Orton Jr and Dick Slater would attack Flair for the bounty which seemingly took Ric out with a career-ending neck injury. Flair would make the triumphant return though and beat Race for the championship in a bloody steel cage match at the first ever Starrcade.

Ric Flair will always credit Race igniting his career and passing him the torch hence why it’s in the top three Ric Flair rivalries.

The way Ric Flair credits the likes of Harley Race and Dusty Rhodes for elevating him to a top star is the same way the Stinger could credit Ric Flair for elevating his career. If this was an article about Sting’s greatest rivals, Ric Flair would be number one. Their feud spanned over four decades as it started in the 1980s and ended in the 2010s. When Sting showed up in JCP/WCW he was so charismatic, magnetic, and an instant fan favorite with his over-the-top personality, that you knew he was going to be the perfect foe for Ric Flair who loved the spotlight to be on him.

In 1988, Sting challenged Flair for the World Championship at the first Clash of the Champions which ended in a 45-minute time-limit draw. Sting would go on to feud with Flair’s Four Horsemen stable mates and also would face Flair throughout the next couple of years. In the Summer of 1989, Sting came to the aid of his old-rival Ric Flair when the odds were stacked against him in a feud with Great Muta and Terry Funk. This led to Sting being invited to join the newly reformed babyface Four Horsemen stable. However, when Sting earned the opportunity to challenge Flair for the championship they kicked him out of the group. Sting and Flair would face off at the Great American Bash where the Stinger would win the World Championship for the first time in an unforgettable moment.

The two would continue to be rivals in the years following, including the infamous Black Scorpion angle, wrestling on both the first ever and last ever episodes of Monday Nitro, and even continued their feud in the 2010s in Total Nonstop Action.

Dusty Rhodes was one of Ric Flair’s influences and mentors early in his career. When Ric Flair finally found himself though he couldn’t be any more different than Rhodes. Rhodes was the blue-collar common man who didn’t have the typical wrestler physique but was full of heart and fire. He was the son of a plumber and instantly relatable. Ric Flair was the “limousine ridin’, jet flyin’, stylin’, profilin’, kiss stealin’, wheelin dealin’ son of a gun” with all the arrogance and money in the world. Flair was self-obsessed and less relatable as he felt like he was better than everyone else. The things they had in common were their charisma, unique swagger, the gift of gab, and the ability to tell a story in the squared circle. It was during Rhodes’ rivalry with Ric Flair that we got the famous “Hard Times” promo.

Their rivalry stretches all the way back to the mid-1970s as they had their first matches in 1975. It really took off in the 80s once the World Championship became involved. Flair would beat Dusty Rhodes for his first World Championship in somewhat of a shocking victory in 1981. Although they continued feuding off and on throughout the years, in 1985 things really picked up. The Four Horsemen was formed during Flair’s feud with Rhodes. The segment where the Horsemen broke Dusty’s arm was some of the most captivating television at the time. They would feud all over America in front of sell-out crowds while making a lot of money. Rhodes would beat Flair for the championship at the Great American Bash in a Steel Cage match. Flair would win it back but they continued to create exciting television with one another until Rhodes left JCP in 1988 when they had their last ever singles match. They would not wrestle each other again in the 90s. But interestingly enough, they teamed up in their last ever match together.

Their rivalry also extended in real-life backstage as the two were always trying to one-up each other in showing off who was more successful. It’s hard thinking about either man without thinking about the other. WOO!