Through his career as a professional wrestler, Nature Boy Ric Flair made his name as one of the best of all-time. He ruled the NWA in the '80s while Hulk Hogan was running wild in WWE. When Flair made his way to WWE, he took over there too and won the world title in a Royal Rumble match. Through his career, Flair won 16 world titles.
However, for a wrestler to have a great career, he needs great rivals who can push him to the limit. That has been no problem for Ric Flair, who has had several of the best matches in wrestling history. Here is a look at the 10 best Ric Flair matches ever, from his days in the NWA to WWE to his eventual retirement.
10 RIC FLAIR VS. STING (CLASH OF CHAMPIONS)
If there is one man that Ric Flair will always be connected with, it is the man called Sting. Flair handpicked Sting to be his successor, and it was a great choice as Sting went on to become the face of WCW during the Monday Night Wars, and he was there thanks to Flair putting him over so well in their feud.
It all started at the first-ever Clash of Champions event in 1988. This was the most important match of Sting's career, and the Flair made the still young Sting look like a star. It ended up as a 45-minute draw, and Sting was declared the future of the business.
9 RIC FLAIR VS. VADER (STARRCADE 1993)
Before he went to WWE and allowed the company to bury him beyond recognition, Big Van Vader was one of the hardest hitting, most dangerous stars in the world. He was so scary that Hulk Hogan didn't want to work with him when he came to WCW. However, Flair does not pass up a challenge.
Vader and Flair battled at Starrcade 93 and beat Vader to win the WCW world championship, which was different from the NWA title he held 10 times before. While Flair was a star before this, his win over Vader after returning to WCW from WWE was career-defining, and it was one of the best championship wins of his career.
8 ROYAL RUMBLE (1992)
When Nature Boy Ric Flair arrived in WWE, he was a star. For those who read the Apter magazines in the '80s, they knew all about the NWA world champion and wanted to see how he did against the WWE superstars. For those who didn't read them or watch Crockett Promotions, Bobby Heenan was there to put him over big-time.
Then, Ric Flair entered the 1992 Royal Rumble as the third entrant at the age of 42. He outlasted names like Undertaker, Hulk Hogan, and Sycho Sid, and ended up winning the entire thing to become the new WWE world champion, his first reign with that title. He was an immediate WWE star.
7 RIC FLAIR VS. SHAWN MICHAELS (WRESTLEMANIA 24)
While most of Ric Flair's best matches came in the NWA and WCW, he had a pair of classics in WWE as well. In the 1992 Royal Rumble, at the age of 42, he won the WWE world title. Against Shawn Michaels at WrestleMania 15 years later — at the age of 57 — Flair had another instant classic.
Honestly, by this time, Flair was nowhere near his peak. He was older, slower, and couldn't do as much athletically in the ring as he could before. However, Flair was still a master storyteller and was in the ring with one of the best of all-time in HBK. Shawn won the match and retired Ric Flair on the biggest stage of them all.
6 RIC FLAIR VS. BARRY WINDHAM (CROCKETT CUP 1987)
It is hard to pick out one match between Ric Flair and Barry Windham that was the best of their series. They had a great match at Beach Blast in 1993 right before WCW left the NWA banner. They had another great match at Slamboree in 1994. The two former partners in the Four Horsemen always tore down the house.
However, their best match came years before those two battles. In 1987 at the annual Crockett Cup event, Flair put his NWA world title on the line against Windham. The two battled in a hard-fought match that went 25 minutes and ended with Flair holding the tights for the cheap win. Windham was one of the best in the business in 1987.
5 WAR GAMES (GREAT AMERICAN BASH 1987)
Nature Boy Ric Flair is one of the best singles wrestlers in history. However, he is also great in other types of matches. The Royal Rumble in 1992 showed Flair at his best. However, he was also in the first-ever War Games match in 198 at the Great American Bash. This match was a rousing success and became one of NWA fan's favorite gimmick matches.
This specific match had The Four Horsemen, consisting of Ric Flair, Arn Anderson, Lex Luger, Tully Blanchard, and manager J.J. Dillon taking on The Road Warriors, Dusty Rhodes, Nikita Koloff, and manager Paul Ellering. While they took the easy way out by having Dillion submit for the loss, this match was gloriously violent and a highlight of old-school NWA.
4 RIC FLAIR VS. RICKY STEAMBOAT (CHI-TOWN RUMBLE)
Yes, all three of the Ric Flair vs. Ricky Steamboat matches are on this list because they are that good. Forget about Tomasso Ciampa vs. Johnny Gargano and Stone Cold vs. The Rock — this was the best trilogy in professional wrestling history. This was their first match in February 1989 at the Chi-Town Rumble.
Flair was the evil heel and Steamboat, the ultimate babyface. Even with a referee knockout (the legendary Tommy Young), Ricky Steamboat held on to win the match and win his first-ever NWA World Championship with a small package.
3 RIC FLAIR VS RICKY STEAMBOAT (CLASH OF CHAMPIONS VI)
The second match in the Ric Flair vs. Ricky Steamboat series too place in April 1989, two months after The Dragon won the NWA world title. This was Clash of the Champions VI: Ragin' Cajun, and this time Ricky was defending his title against Flair. This match went for almost an hour, and it never felt like it.
There needed to be one more match between the two, but if Steamboat won here, it would still make him the official winner of the feud. So, the ending was perfect. Steamboat pushed off the turnbuckle and landed on Flair. Tommy Young counted to three and declared Steamboat was the winner. However, both men's shoulders were down, so a third match was necessary.
2 RIC FLAIR VS. RICKY STEAMBOAT (WRESTLEWAR)
The final match in the Ric Flair vs. Ricky Steamboat trilogy took place one month later. It was at WrestleWar: Music City Showdown, and by this time, both men had earned each other's respect. Flair was still a dirty wrestler, and Steamboat was still the clean-cut champion who refused to cheat.
This match was not the hour battle of the prior month, but still went 30 minutes and saw the two men doing everything they could to win. This time, it was Flair who took advantage of a Steamboat mistake to wrap him up with a cradle and win his title back. The two men fought three times, and every match was brilliant.
1 RIC FLAIR VS. TERRY FUNK (CLASH OF CHAMPIONS IX)
Terry Funk was an NWA world champion in the '70s, and by 1989, most people figured he was over-the-hill and past his prime. Remember, this was still a few years before his reinvention in ECW, where Funk became a hardcore legend. This feud started after Flair beat Steamboat for the world title at WrestleWar.
Funk congratulated Flair on the win after the match and then asked for a title shot. Flair dismissed him, which Funk took as disrespect, and he killed Flair, piledriving him through a table. The two battled at Clash of Champions IX in an I Quit match, and it was a brilliant display of violence that Flair ended up winning, proving he could wrestle any type of match put in front of him.