Being a wrestling legend doesn’t shield you from having some embarrassing moments throughout your career in the ring. Whether those moments are enjoyable surprises or questionable booking decisions, the fact is that they still remain memorable. Especially because they're associated with people better known for glory and victories.
So, here is a list of some of the most humiliating losses the greats have suffered. Moments that will live on forever, for as long as there are upcoming generations interested in professional wrestling!
10 Chris Jericho Vs Fandango
Not to dismiss the talent of Johnny Curtis a.k.a Fandango, but he isn’t exactly the most iconic wrestler. Curtis did his best with the hand he was dealt, and managed to get far with his charisma and his catchy theme song. But for Jericho to lose to him on the grandest stage of them all, it definitely didn’t feel like a deserved victory.
Not to mention that legends need to be more careful with who they put over or they risk cheapening the value of their rub. This is an even more embarrassing loss in retrospect, considering the divergent roads the two wrestlers’ careers have taken since then.
9 Razor Ramon Vs 1-2-3 Kid
Monday Night Raw is the iconic show that it has become because of moments like this. A moment that had Sean Waltman (a.k.a the Kid) get an upset win over the cocky Razor Ramon.
This win launched Waltman’s career. He became 1-2-3 Kid after the match, and eventually X-Pac - among many other variations of the same name. Not only did this win affect the victor, but it also helped turn the established star in Razor Ramon into a face eventually.
8 The Rock Vs The Hurricane
Hollywood Rock is considered by many to be the best variation of The Rock’s character we've seen throughout his legendary WWE tenure. It allowed him to showcase his excellent heel work and natural charisma to the fullest.
However, one WWE Superstar of that time took offense to everything the Rock has become and confronted him about it. This memorable feud was filled with comedy gold and it continued to develop until the two faced one another in the ring, where the Hurricane managed to pull and upset and beat the Rock (with the help of Stone Cold Steve Austin).
7 Kurt Angle Vs Eugene
There is no doubt that Eugene’s character wouldn’t fly in today’s wrestling world, due to its offensive nature. Not to mention that it's quite cringeworthy in retrospect. At the time, however, he was one of the biggest acts on the roster for a while. He even became an Olympic gold medallist for a brief time.
Eugene was able to achieve this impressive feat when he managed to avoid getting tapped out by Kurt Angle for 3 minutes, as part of the Kurt Angle Olympic gold medal invitational that was taking place at the time.
6 John Cena Vs Kevin Federline
WWE’s love for mainstream validation is well-known. All you have to do is look at the huge number of celebrities that have graced the WWE ring over the years. While some of those have been essential to help elevate the WWE to the next level, others have been quite the desperate attempt.
When Federline got into an odd feud with John Cena, it did feel like one of those instances. However, you have to give props to Federline, who managed to channel his natural heel charisma. On the first Raw of 2007 (and with some help from Umaga), he even managed to get a pin win over Cena.
5 The Undertaker Vs Maven
Maven was the first Tough Enough competition winner. However, he will forever be remembered for his fan-favorite theme song as well as his, now iconic, crisp looking drop-kick that ended up eliminating The Undertaker from Royal Rumble 2002.
As if that wasn’t enough by itself, you had a mix of JR’s iconic commentary and the crowd’s monstrous pop, as well as Maven’s celebration and Taker’s facial reaction on top of it all. Fast forward a few weeks later and Maven is pinning Taker on an episode of SmackDown for the Hardcore Championship, with the help of The Rock.
4 Ric Flair Vs Rico
Ric Flair’s tenure in WWE after the fall of WCW isn’t necessarily the greatest look for an all-time great, from a win-loss perspective. He has lost a remarkable number of matches to so many wrestlers. One of those is Rico, who wasn’t even taken seriously with the gimmick that the WWE saddled him with.
This win wasn’t necessarily to push Rico, as much as it was to showcase how far removed Flair was from his younger former self. A segment with Triple H followed and it touched on that same idea. Eventually, this was the starting point that led Triple H and Flair into forming Evolution.
3 Hulk Hogan Vs Billy Kidman
During the dying days of WCW, Billy Kidman managed to pin Hulk Hogan three times in a row. This was part of the push intended for the younger talent over the established big names, in hopes of creating some new stars through The New Blood vs the Millionaire’s Club feud.
However, it reeked of desperation, especially considering that Kidman didn’t have enough charisma to benefit from this type of push. While the idea itself is an admirable one in theory, it backfired and showcased the panic that was running amok backstage, after years of terrible booking and younger talent being buried.
2 Triple H Vs The Brooklyn Brawler
It’s true that it was a three-on-one handicap match, but the intention of this bout was for Triple H to flex his abilities over a number of jobbers. Of course, one of those jobbers was none the other than the jobber’s jobber, the Brooklyn Brawler. After Triple H pinned Kai En Tai, he was left to face The Brooklyn Brawler in a one-on-one situation.
Nobody would have even imagined that the impossible would happen, but then the three count took place: Triple H was on the receiving end of a humiliating loss, with some help from Chris Jericho.
1 A.J. Styles Vs James Ellsworth
James Ellsworth was not even supposed to have the career he has had, considering he was just used as a jobber to put over Braun Strowman during his monster push. However, he managed to get himself over with the WWE Universe when he uttered his legendary “any man with two hands has a funny chance” line from his in-ring interview prior to the match with Braun Strowman walking down the ramp.
Eventually, he got another shot during the Dean Ambrose and A.J. Styles feud. He scored a win over the Phenomenal One, thanks to the former (who happened to be the special referee that night).