13 Cringey Moments From Ric Flair's Career Fans Should Know

Read update

Ric Flair’s cringe-worthy moments in the wrestling world sadly date back to the 1990s in WCW, in a number of cases over choices that were beyond his control as the powers that be plugged him into unfortunate situations that risked tarnishing his legacy. Flair hasn’t been a saint either, though, including making some regrettable choices in the public eye over social media related to his podcast endeavors. While the sixteen-time world champion will still go down as one of the best-respected wrestlers who ever lived, he can also be a complicated figure for some hardcore wrestling fans to celebrate wholeheartedly.

Few wrestlers are more well-known in the world of pop culture than Ric Flair, with the Nature Boy being someone that even non-wrestling fans are aware of. He has had a fantastic career inside the ring, putting on some incredible matches in unforgettable storylines which helped Flair capture countless titles along the way.

However, while the two-time Hall Of Famer has been involved in a lot of positive situations, there have also been a few cringe-worthy spots in his career as well. Some of them were entertainingly bad, while others were poor to watch, and fans should be aware of this side of Flair as well.

UPDATE: 2023/09/08 16:30 EST BY MICHAEL CHIN

Ric Flair’s cringe-worthy moments in the wrestling world sadly date back to the 1990s in WCW, in a number of cases over choices that were beyond his control as the powers that be plugged him into unfortunate situations that risked tarnishing his legacy. Flair hasn’t been a saint either, though, including making some regrettable choices in the public eye over social media related to his podcast endeavors. While the sixteen-time world champion will still go down as one of the best-respected wrestlers who ever lived, he can also be a complicated figure for some hardcore wrestling fans to celebrate wholeheartedly.

13 Ric Flair Losing On Vader’s Behalf At Uncensored 1995

Hulk Hogan v Vader Uncensored 1995 Cropped

WCW Uncensored 1995 looked to mark the blowoff of the feud between Hulk Hogan and Big Van Vader in a main event strap match. Things went off the rails when Ric Flair got involved.

RELATED: Hulk Hogan Vs. Vader: How WCW Botched This Dream Feud, ExplainedIt’s not The Nature Boy’s fault that things went awry, but as he wrote in his book, he was cajoled into returning early from a retirement angle to interfere in the match. The comeback undermined the gravity of him losing a match with his career on the line a few months earlier and was only exacerbated by Flair appearing in drag—a disguise so he could get the jump on Hogan. The cherry on top of this embarrassing outing was that Flair nonsensically lost on Vader’s behalf as The Hulkster wound up dragging The Nature Boy, not Vader, to all four corners of the ring to somehow be declared the winner.

12 Ric Flair Unmasked As The Black Scorpion

Ric Flair’s rivalry with Sting was long and winding. It appeared that Sting had a momentary reprieve from that storyline when he was terrorized by the masked Black Scorpion—an angle that wasn’t well-received but was at least different.

However, when WCW’s plans for a surprise reveal of The Black Scorpion’s identity went awry. Al Perez had been working under the hood but abruptly left the company. Some rumors suggest WCW intended to debut The Ultimate Warrior in the gimmick, but he wouldn’t end up signing with WCW for nearly eight years. In lieu of a better solution, WCW cast Flair in the role—a redundant plot point and a spot he himself has called one of the most embarrassing of his career.

11 Ric Flair’s Public Feud With Mark Madden

Ric Flair has an uncomfortably long history of public break-ups with long-time friends. One of the most awkward instances of this came in March 2022 when The Dirtiest Player in the Game parted ways with friend and podcast co-host Mark Madden.

Madden announced he was leaving the show over Twitter, only for Flair to correct him in front of the masses, saying Madden had been fired. The exchange between the two continued over social media, and while the particulars of how their partnership ended remain murky, Flair in particular came across poorly for how he chose to present himself and airing dirty laundry.

10 A Game Of Musical Chairs

Over the years WWE has booked some strange concepts that have been cringey to watch, and one of them involved Ric Flair. This saw him be part of a musical chairs game, which was done to create a number one contender for the Intercontinental Championship.

It was a ridiculous segment that didn't make anybody look good, and was something that didn't help build a credible storyline for the title. Considering Flair's history in this industry, seeing him strut around some chair was a low moment for him.

9 Lacey Evans Storyline

The last major storyline that Ric Flair ended up being involved in during his WWE career was one that had people cringing as he turned on his daughter to work alongside Lacey Evans. It was an odd angle as the company teased and alluded to the idea that Flair and Evans were in a relationship.

While nothing was ever made official, there were enough hints to make it clear that was the idea that fans were supposed to think, which was a strange one. It wasn't something that people wanted to see, and it was a negatively cringey situation for him to be involved in.

8 Ric Flair's Last Match

Much like many wrestlers from his generation, Ric Flair has had a difficult time ending his wrestling career. Despite the fact he got a great send-off by WWE against Shawn Michaels, the Nature Boy has gotten back in the ring several times, including a recent match in 2022 which was billed as his last-ever encounter.

Flair teamed with Andrade El Idolo to face Jeff Jarrett and Jay Lethal, and it was certainly cringe-worthy at times, with Flair no longer looking at his best. The match wasn't the best, but fans have split opinions on whether it was fun to see or not. there's no doubt that moments like Flair passing out from dehydration or faking a heart attack were cringe-worthy to see.

7 Trying To Kiss Becky Lynch

Another cringey moment in Ric Flair's career came when he was working as Charlotte Flair's manager, which often saw him cheat to help his daughter pick up victories. However, at the 2016 Royal Rumble, he did so in a rather unconventional, and creepy manner when he kissed Becky Lynch.

It's a side of Flair that is often spoken about in a negative light, and there's a reason WWE took this out of the PPV with edits after the fact, so any new fans would miss it. This simply wasn't a good spot, and shouldn't have happened.

6 Announcing Team Flair vs. Team Hogan

Whenever WWE heads to Saudi Arabia they like to take legendary names with them, and in 2019 it was Ric Flair and Hulk Hogan who went. Obviously, WWE didn't want them wrestling so the company set up a Team Flair vs. Team Hogan match, but the creation of it was cringe-worthy to watch.

The two men, clearly past their primes, decided to fire up as if they were going to fight, only for things to then turn into jokes. It was strange to watch, and is something that many may have found funny as they relived their primes for a brief segment.

5 Hall Of Fame Speech Cut Short

The Hall Of Fame is a huge deal for any wrestler, but when you have the legacy of Ric Flair it becomes an even bigger deal. When he was first inducted, fans were excited to hear him tell stories of his career, but Vince McMahon ended up worrying about the timing of it.

That led to a cringe-worthy moment as Triple H had to go up to him, mid-speech to inform the Nature Boy his time was up. When Flair just continued, the Game awkwardly had to go again, which was an odd situation to witness.

4 Appearing On Miz TV

In 2013 WWE attempted to get The Miz over as a babyface by having Ric Flair become a manager who would guide him, which was a strange enough situation as it was. He passed the Figure Four Leglock to him, and the two would work together for a brief period.

However, during this he ended up on Miz TV, which led to a cringey segment as he and Miz went back and forth hitting Flair's catchphrases as the Nature Boy strutted around the ring, bouncing off the ropes, which was a strange moment that fans either found hilarious or terrible.

3 Being Committed In WCW

Another random moment that came in Ric Flair's career was during his WCW storyline against Roddy Piper in WCW, when the company decided that the Nature Boy should be committed to an asylum. This led to him being shown with patients who had mental difficulties, while Flair was being as charismatic as possible.

He would wear a robe and strut around dropping his usual catchphrases in segments that were supposed to be funny, but ultimately felt very awkward and cringey to watch.

2 A Fake Heart Attack

The idea of a wrestler pretending to have a heart attack inside the ring is something that would never happen nowadays because it is insane to think about, purely because it doesn't make anybody look good. However, during Ric Flair's WCW career that is a moment that took place with him.

It wasn't a good look for Flair in that moment, especially because some of the fans appeared to be legitimately concerned about his status. This was something that everyone involved would likely change if they had the option to, but it did end up taking place, with fans not being keen on it.

1 The Woo-Off

One cringey moment from Ric Flair's career that people need to know about came from his time working in TNA with Jay Lethal. The younger wrestler is well-known for his ability to cut impressions of certain wrestling legends, and Ric Flair just so happens to be one of them.

That led to them having a 'Woo-Off,' during one episode of the show. They went back and forth screaming the classic catchphrase at each other as things became increasingly more over the top. It was a ridiculous segment, but it has become popular over time, which is why fans should be aware of it.