10 Weirdest Moments Of Ric Flair's Career

Starting his career in 1972 and retiring in 2011, Ric Flair is considered one of the greatest of all time, a legend who’s done it all, seen it all, and won (at least) 16 world titles in the process. He’s been both babyface and heel, popularized how stables function in wrestling, and competed in some of the greatest matches of all time as well as some of the worst.

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But let’s not focus on the good or bad of Ric Flair’s career. Let’s take a look at some of the weirdest things he’s done in his long career, some of which are classic and some of which are regrettable.

10 Having A Woo-Off With Jay Lethal

Despite wrestling what some would call the perfect retirement match at WrestleMania XXIV, Ric Flair continued to wrestle outside of WWE and found himself in Impact Wrestling. While some consider it a tarnishing of his reputation, it did create one of the best moments of his late-career as Jay Lethal was revealed as being able to do a spot-on impression of The Nature Boy -- and not just the signature Woos, but his actual promo style. This led to an intense, hilarious segment where both Flair and Lethal dueled via cartoonish renditions of all of Flair’s mannerisms, including the woos.

9 Buried Alive

It’s not uncommon for wrestlers in storylines to get attacked and even abducted, but Flair’s experience in 1999 is pretty exceptional. There were plans for a storyline where The Filthy Animals would kidnap and bury alive various legends who’d then band together to form a counter group, but that never happened. All that remained of the concept, however, was a segment of Nitro containing footage of the Animals burying Flair in the Las Vegas desert. However, Flair would eventually return unscathed, and no mention of his abduction and attempted murder was made.

8 Having His Hall Of Fame Speech Cut Off

The WWE Hall of Fame is a strange beast unto itself. There’s no physical building, the lineup of inductees is basically “wrestlers who aren’t on the outs with the company,” and even the ceremony itself has offered some strange moments. Unexpectedly, one such moment happened during Ric Flair’s induction.

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Flair -- again, considered one of the all-time greats -- ended up going incredibly long in his speech, with no sign of stopping. This caused Vince McMahon and the rest of the production crew to get nervous, so Triple H was forced to lean in and tell Ric Flair to hurry up and wrap up the culmination of his entire career, a decision that drew boos from the live crowd.

7 Ric Flair Is The President

Flair was a great in-ring competitor, but he was also unparalleled on the microphone, capable of delivering memorable, high-intensity promos. He also had a tendency to strip off his clothes in the heat of a really good promo, which felt extremely common as late 1990s WCW went on. In one memorable promo, The Nature Boy stripped down to his (University of Florida) boxer shorts and confronted a (fully clothed) Roddy Piper, bellowing “I am Ric Flair, the President of the United States” -- one of Flair’s greatest out-of-context moments.

6 The Dusty Rhodes Costume

One of Flair’s most legendary feuds was with Dusty Rhodes in the 1980s, and in 2001, he was party to Jeff Jarrett’s feud with Rhodes’ son Dustin. In anticipation of a tag match between Dusty Rhodes/Dustin Rhodes and Ric Flair/Jeff Jarrett, Jarrett wrestled a goofy one-minute squash match against a guy in a fat suit, cowboy hat, and a mask that looked vaguely like Dusty Rhodes. Soon enough, the fake Dusty would unmask to reveal Ric Flair, creating an incredibly bizarre image of Ric Flair in a fat suit.

5 The Final Nitro

March 26, 2001, was an emotional night for WCW, as it would air its swan song in the form of the final episode of Monday Nitro. The last bout on the program was between Ric Flair and Sting, whose rivalry defined the company. It’s a short match lasting all of seven minutes, but it’s a weird moment because Flair infamously wrestled in a T-shirt. This is because Flair just had surgery and his physique wasn’t actually ring-ready, but it’s still a weird quirk of this historic moment in wrestling.

4 Ric Flair Falls Into A Hole

At Impact Wrestling’s 2010 Destination X PPV, a main event World Title match between AJ Styles and Abyss ended in a DQ because Abyss chokeslammed AJ through the mat. That’s a weird enough booking decision, but what followed was even weirder.

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In the aftermath, Ric Flair and Desmond Wolfe ran in to brawl with Abyss, but both end up falling into the same hole that Styles went down in the most cartoonish fashion. This is ostensibly supposed to be a “send fans home happy” moment, but it ultimately came off as strange above everything else.

3 Ric & Lacey

It’s inevitable -- especially in WWE -- that a given manger will end up betraying their client in favor of a new client, causing a feud. In 2021, Ric Flair ended up ditching his daughter Charlotte in favor of Lacey Evans, who began wearing Ric’s robes to mess with the younger Flair. There was also that weird moment when Charlotte found her father doing very close-contact training with Evans. The angle got weirder once Lacey Evans got pregnant in real life, which resulted in on-screen hints that the kid was Flair’s. The storyline was quickly dropped once Evans had to leave television, and even Flair himself objected to the program.

2 Flair’s Commitment Issues

It’s not beyond the pale to say that Flair’s various tics and tendencies -- the wooing, strutting, the stripping, elbow dropping his own jacket -- are all pretty peculiar, especially outside the context of wrestling. WCW ended up making Flair’s strangeness canon once Piper got The Nature Boy committed to an asylum. What followed were skits wherein Flair would do all his Flairisms while wearing his signature robe and surrounded by extras doing their best impressions of patients in One Flew Over the Cuckoo’s Nest.

1 Musical Chairs

On the 7/5/2004 episode of Raw, the ever-problematic Eugene was the guest boss of the show, so he opened the show by booking a game of musical chairs featuring Tomko, Stacy Keibler, Chris Jericho, Jonathan Coachman, Jerry Lawler, Tajiri, and Ric Flair. The whole segment -- set to “Pop Goes The Weasel” -- is weirdly wholesome and charming because it’s so out of character for pro wrestling, especially WWE circa 2004. Flair ends up losing this game by strutting too much, and Jericho ends up getting the win. To make it weirder, this musical chairs game was for a shot at the Intercontinental Championship.

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