The year 1991 saw a major defection in pro wrestling, as Ric Flair began to experience with WCW management, leading him to jump ship to rival WWE — and with the competition’s World Heavyweight Championship around his waist, to boot. Flair had spent the 1980s as a top star and a decorated champion, a trend that continued in his new stomping grounds as he’d become a two-time WWE Champion before he returned to WCW in 1993.

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Following WCW’s demise in the early 2000s, “The Nature Boy” returned to WWE, where he spent most of the rest of the decade. Over the course of those two runs, he engaged in a number of memorable rivalries with top stars and midcarders alike, so let’s take a look at all the ones worth talking about, starting with the least satisfying.

10 Hulk Hogan

Ric Flair vs. Hulk Hogan

When Ric Flair initially arrived in WWE in 1991, he went after pretty much every notable wrestler in the company, including top babyface Hulk Hogan. Flair ended up getting under the Hulkster’s skin in a major way by November, as he cost Hogan a match — and the WWE Championship — against The Undertaker at Survivor Series. It seemed like a big match at WrestleMania 8 was in the cards, but suddenly plans changed and Flair fought Randy Savage in the middle of the show. Hogan and Flair did have some matches in WWE, however, including a tag match against one another on Saturday Night’s Main Event and a couple of matches broadcast on WWE’s MSG Network show.

9 Roddy Piper

Ric Flair vs. Roddy Piper

Before running afoul of Hulk Hogan, Ric Flair initially run afoul of Roddy Piper, taking him on in a Survivor Series match the same night that he interfered in Hogan’s match. Bolstered by Ted DiBiase, The Mountie, and The Warlord, Flair would defeat Piper’s team, which included Bret Hart, Virgil, and The British Bulldog. That wouldn’t be the end of their relationship in WWE, however — during Flair’s second run, the two former rivals would become tag team partners in 2006, going as far as capturing the tag titles together.

8 Mr. Perfect

Mr Perfect Vs Ric Flair

During Ric Flair’s early ‘90s run, he had a couple of guys in his corner: Bobby Heenan as his manager and Mr. Perfect as a ringside enforcer. However, by the end of 1992, Mr. Perfect would get fed up with Heenan’s antics and turn face, joining Randy Savage in a tag match against Flair and Razor Ramon.

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After Perfect eliminated Flair from the 1993 Royal Rumble, the two former associates had a Loser Leaves WWE match on the third-ever episode of Raw, a forgotten classic that marked Ric Flair’s departure from the company.

7 Vince McMahon

Ric Flair vs. Vince McMahon

As soon as the WCW/ECW Invasion storyline ended with the dissolution of the invading Alliance, WCW got one final win with the return of Ric Flair to WWE in November of 2001 and the revelation that “The Nature Boy” was now a co-owner of the company. This, of course, drew the ire of WWE boss Vince McMahon, leading to several encounters between the two men. Their first, a street fight at Royal Rumble 2002, was Flair’s first televised WWE match since 1993. Five months later, it would all come to a conclusion with a match on Raw for full-control of WWE, which ended with McMahon winning thanks to some help from Brock Lesnar.

6 Carlito

Ric Flair vs. Mick Foley

Most of Ric Flair’s WWE feuds were against some of the biggest names in the company, but he also had a memorable storyline with Carlito. After questioning the midcarder’s passion and work ethic, the two initially formed a tag team, only for tensions to mount and a full-on feud ensued, with Flair putting away his young rival at Judgment Day 2007. Two years prior, the two men also feuded over the Intercontinental Championship, with Flair dethroning Carlito as champion and then defending the belt in a rematch that proved to be one of Carlito’s best matches ever.

5 Triple H

Ric Flair vs. Mick Foley

Triple H and Ric Flair were stablemates in the heel faction Evolution from 2003 to 2005, but by October 2005, Triple H was out due to injury and Ric Flair had turned babyface in the meantime. Upon returning to action that month, Trips turned on his friend and mentor, and the two clashed in several brutal matches. After Flair managed to retain the IC Strap at Taboo Tuesday, weeks later the two had an acclaimed Last Man Standing match at Survivor Series, which Triple H won.

4 Edge

Ric Flair vs. Mick Foley

In 2005, Ric Flair got arrested by the police following a road rage incident, which of course became a matter of kayfabe concern when Edge began to make fun of it on his talk show segment, The Cutting Edge. The two would meet inconclusively at New Year’s Revolution, but that wouldn’t be the end of their feud.

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After Ric Flair interrupted Edge and Lita’s in-ring “Live Sex Celebration,” the two rivals would finally collide in an awesomely violent TLC match on Raw that saw Edge retaining his newly won WWE Championship against Flair.

3 Mick Foley

Ric Flair vs. Mick Foley

The Edge feud wouldn’t be the only instance of real life issues becoming wrestling angles for Ric Flair in 2006. Flair and Mick Foley had real-life enmity that became fodder for an in-ring rivalry, starting with Flair winning a 2/3 falls match against Foley at Vengeance. Two months later would come the big showdown: a great I Quit match at SummerSlam 2006, which ended with Ric Flair getting the win over his kayfabe and real-life rival.

2 Shawn Michaels

Ric Flair Vs Shawn Michaels (WrestleMania XXIV)

In late 2007, Ric Flair proclaimed that he would never, ever retire, which prompted aforementioned rival Vince McMahon to prove Flair wrong by placing a stipulation of every Ric Flair match: if he lost, he would have to retire. “The Nature Boy” spent months defending his livelihood against a parade of stars, but it was Shawn Michaels who finally got the job done. Their match at WrestleMania 24 was a classic — not only was it well-wrestled, but Michaels delivered an iconic moment by uttering “I’m sorry, I love you” before ending Ric Flair’s WWE career.

1 Randy Savage

Ric Flair vs. Randy Savage

As far as WWE rivalries, Ric Flair’s best feud was arguably against Macho Man Randy Savage, in an angle that involved both great wrestling and also a compelling storyline. After Flair won the WWE Championship in the 1992 Royal Rumble, Savage emerged as his WrestleMania 8 challenger, and the mind games began to surface as Flair tried to convince Savage that he had dated Miss Elizabeth before Savage. Savage would defeat Flair at ‘Mania, but their rivalry would continue, including “The Nature Boy” interfering in Savage’s match with The Ultimate Warrior at SummerSlam, injuring the champ in the process. The injury would come into play days later as Ric Flair successfully dethroned Randy Savage to win back the title.