Top 20 WTF moments in UFC history

In a sport once referred to by Republican Presidential nominee John McCain as “human cock fighting”, it’s an easy assumption that there have been a lot of wild, bewildering, and downright weird moments in the past 20 years. The UFC has had its fair share of situations which have left those watching saying, “WTF”. There have been strange fights, strange entrances, and more than enough strange people involved in the UFC’s history. Here are the top 20 WTF moments.

#20: It’s “Championship” not “Challenge”

Doomed from the start. It’s absolutely incredible in every way imaginable that the UFC has lasted this long and grown this big. For all those watching 20 years ago or who rented the VHS tape from the “special interest” section of a local video store or who are catching up on the history via the internet, the very first words ever uttered at UFC 1 were an enormous mistake.

“Hello, ladies and gentlemen, you’re about to see something you have never seen before - the Ultimate Fighting Challenge.”

It’s championship! IT’S CHAMPIONSHIP! Unbelievable. The first pay-per-view event of its kind was introduced and hosted by karate and kickboxing champion Bill “Superfoot” Wallace who was in rare form on November 12th, 1993. Moments after screwing up the company’s name in his first breath, Wallace burped while mentioning the McNichols Sports Arena. Actually, “Superfoot” belched the word arena, which he did politely excuse himself for.

That was only the beginning. The very beginning of a night of fights, which would feature a tooth getting kicked out of sumo wrestler’s head and the watershed moment for Brazilian jiu-jitsu. The entire event’s conception was a giant commercial for a brand of submission wrestling taught by the Gracie family and it was wildly successful as that martial art has become bigger by the day. Subsequently, the sport of MMA has become pretty big too, but a lot of that came years later in events far different than the original.

#19: The era of nipple pinching

There was definitely a time when some of the best and most famous fighters in the UFC started all of their fights by pinching their nipples. Yep. It was all thanks to current UFC welterweight champion Georges St-Pierre and something he read in a book. Supposedly, St-Pierre learned that Roman soldiers would pinch their nipples for good luck prior to going into battle. Sure, GSP, sure.

Either way, the UFC fighters who comprised Team Jackson’s began doing it in the Octagon. From the Canadian-born champ himself to The Ultimate Fighter 2 winner and former UFC light-heavyweight champ Rashad Evans, and just about everyone else who was a member of the Albuquerque, New Mexico gym was pinching their nipples live on pay-per-view or on free TV.

You just haven’t lived until you’ve seen Keith “The Dean of Mean” Jardine, with that face/goatee that only a mother could love, pinching a nipple or two before getting bloody in a caged-brawl. Of course, guys like St-Pierre and Evans tried to play it off like it wasn’t weird, but good ole’ Jardine would give a little smile to the camera when tweaking.

#18: BJ Penn gets kissed by a dude during entrance

At UFC 94, it was champion vs. champion as multi-division talent and future UFC Hall of Famer “The Prodigy” B.J. Penn was stepping up in weight to rematch Georges St-Pierre for his welterweight title. It was a superfight; it was the superfight. The 155 pound champ fighting the 170 pound champ who roughly 3 years earlier fought to a controversial split-decision.

With Penn heading to face the toughest opponent he could ever ask for and to do it at a higher weight, probably the last thing the fighting Hawaiian needed was to be kissed on the cheek on his way to the Octagon by a known former male prostitute slash heroin addict. Yep. If you paused or rewound when that long haired, tattooed, stringbean of a man pops his head out of the crowd to plant a wet one on the then UFC lightweight champ’s cheek, you may - emphasis on “may” - have recognized turbulent semi-famous rapper Mickey Avalon’s face.

UFC President Dana White has said over and over again throughout the years, that he likes to keep his distance from fighters during fight week and, especially, fight day because he doesn’t want to mess with their mindset. That’s the UFC boss saying that he gives one speech to all the fighters to get them jazzed up, but besides that he doesn’t talk or really interact with any of the fighters because White worries it may mess with their tuned in fighting mentality.

Meanwhile, seconds away from the biggest and most difficult fight of his life, Penn’s got Avalon’s unwanted lips pressed against his face. The MGM Grand’s security failed that night.

#17: Forrest Griffin can cry if he wants to

Not once, but twice. The Ultimate Fighter season 1 winner and former UFC light-heavyweight champion and UFC Hall of Famer and huge fan favorite Forrest Griffin has cried inside the Octagon. Not tears of joy, but bawling in defeat. Honestly, many fighters - male fighters - have cried in and out of the cage, watch any episode of The Ultimate Fighter ever. But, it was simply shocking seeing that raw emotion streaming down Griffin’s face after seeing him in several bloody bouts.

At UFC 66, Griffin lost inside the Octagon for the first time in a really real way. Two fights earlier, Griffin lost a split-decision to Tito Ortiz, but that back-and-forth battle was nothing like this. Team Jackson product Keith Jardine tore apart Griffin in less than a round by dropping Griffin and then blasting him with vicious ground and pound, which brought a quick close to the bout. Whether it was the TKO or losing a fight he was the favorite to win, when the cameras spun around to see Griffin’s reaction - he was sitting against the cage sobbing.

Obviously, Griffin received and still does receive a lot of flack for that unflattering moment, so when Griffin found himself in a similar situation a few years later getting flattened by then UFC middleweight king Anderson Silva - Griffin took action. That “action” was running out of the Octagon to shed any tears in the locker room instead of in front of an entire arena of jeering and very unforgiving Philadelphia fight fans. While, he got additional flack for that, it was the right decision.

Seriously though, Griffin’s a tough SOB. The man is a 5x Fight of the Night winner and 3x Fight of the Year winner and was in the most famous fight in company history, which he won. Also, Griffin is a solid humanitarian. But, he cried a couple times and that was memorable too.

#16: Lyoto Machida drinks urine

Almost always, his own. There was that one time, just a few months ago, he drank a sexy lady Brazilian TV reporter’s pee and she drank his, which really makes American television seem quite tame. But we digress…

Former UFC light-heavyweight champion Lyoto “The Dragon” Machida pisses excellence and then drinks it every morning. Or at least his Shotokan karate master dad, Yoshizo Machida, does and Lyoto does it most mornings. Either way, the 19-4 striking specialist does drink his own urine as a part of “urine therapy”, which is based in the idea that one’s first pee of the day contains nutrients. Talk about bad morning breath!

The Machidas’ practice of this odd, ancient, and still medically unfounded idea was revealed in a truly TMI episode of UFC’s Countdown show previewing Machida’s rematch title defense against Mauricio “Shogun” Rua at UFC 113. With all the incredibly skillful knockouts Machida has recorded inside the Octagon including the Knockout of the Year crane kick on Randy Couture, there will always be the truly unforgettable detail of this enigmatic fighter’s life that he wakes up, pees in a cup, and then drinks it.

#15: Rousimar Palhares celebrates win while fight is still going on

As many have learned recently, Rousimar Palhares might not be all there in the head. Actually, what has gotten “Toquinho” (translates to “tree stump”) in trouble is stopping his attacks too late, but one of the more confusing moments was when Palhares stopped too early at UFC 134.

In the first UFC event held in Brazil in 13 years, Palhares was picked to fight in front of his home country fans against the New Jersey tough Dan Miller. While many expected the two Brazilian jiu-jitsu blackbelts to engage on the ground, “Toquinho” began the bout winging his massive gorilla arms at Miller and caught him with so big shots. With around 30 seconds left in the first round, Palhares dropped Miller and administered some ground and pound. Referee Herb Dean got awfully close to examine how Miller was defending these punches, but he never signaled Palhares to stop.

Nevertheless, Palhares did stop - prematurely. The muscular middleweight walked away triumphantly with arms raised in the air then he hopped onto the top of the cage to see the Brazilian crowd more clearly as he celebrated his win. Things became a bit awkward as Dean then had to inform Palhares the bout did not end and he needed to go back to roughing up Miller if he truly wanted to be the winner.

So, Miller and Palhares shared a moment wear body language can break the language barrier as the two recognized they needed to go back to punching each other in the face. That’s when, Miller nailed Palhares with a punch that nearly KOed the guy who was on top of the cage only seconds ago.

Eventually, Palhares did go on to pick up a unanimous decision.

#14: Nick Diaz and UFC 137

Did you know that UFC 137 was originally supposed to be in Liverpool, England? Crazy, right? There were some scheduling issues and the event was moved to Las Vegas. Pretty wild and weird stuff.

Oh yeah, and then there was all that other stuff where Nick Diaz was supposed to fight UFC welterweight champion Georges St-Pierre for the title in the main event, but Diaz was kicked off the card for skipping a press conference. And then it was revealed at said press conference that GSP was going to defend his title against fellow Team Jackson-Winkeljohn member Carlos Condit who was set to fight B.J. Penn in the co-main event. But that fight didn’t materialize because St-Pierre tore his ACL not long later and was out for a year, and Condit decided he would wait to tangle with the champ. So, the UFC settled with re-instituting Diaz to UFC 137 to have him face his idol, Penn, in the main event. Wait, what?!

For those wondering, that situation had never happened before in the UFC. Diaz missed three separate flights to be at that press conference and, apparently, had been ducking the camera crew following him around for the UFC 137 preview show. Getting pulled from a headlining title fight like that was unprecedented and, in the end, Diaz still was the main event, which is hilarious.

The fight with Penn was one for the ages too. It was all the mean mugging and boxing one can expect and gets delivered each and every time from the Stockton slugger. Easily, the best moment of the fight was something only the elder Diaz would ever do, he headbutted Penn’s pawing jab. Who headbutts their opponent’s fists?!

#13: Paul Daley suckerpunches Josh Koscheck

Ardent critics of the sport and/or the MMA ignorant, probably assume that these blood-thirsty cagefighters have to pulled off each other after every fight with chain lassos. Meanwhile, by far the majority of fights end with handshakes and hugs. In many regards, it’s a very gentlemanly competition with five-minute breaks for accidental kicks to the cup and congratulatory words between opposing coaches regardless of the outcome. But…

There’s always the exception that proves the rule. And for the UFC, it’s British brawler Paul “Semtex” Daley and his post-fight cheap shot against veteran villain Josh Koscheck.

At UFC 113 in a title eliminator for the welterweight belt, Koscheck took a rather boring takedown-heavy decision. The lead-up to the bout was classic Kos with tons of trash talk and promises of knockouts, which Daley and fight fans ate up with a spoon. Of course come fight night, the former NCAA Division I National Champion wrestler from Edinboro University did hit Daley with something, but it wasn’t a punch - it was a blast double-leg takedown. From there, Koscheck rode Daley on the ground and never allowed the KO artist a second to throw hands.

When the clock ran out, Koscheck began his victory lap, but was quickly met by Daley with a left hook that caught Kos on the kisser. Referee “Big” Dan Miragliotta jumped into action and bear hugged Daley while giving him a tongue lashing on proper post-fight etiquette. Later that evening, UFC Prez Dana White revealed that he had banned Daley from the UFC, which has stood to this day.

Daley’s admitted since then that the emotions of the trash talk plus the way the bout played out lead him to the regrettable rash decision. Not to mention, there was that part in the fight where Koscheck pretended he got kneed in the head, which a slow-mo replay revealed that the knee merely grazed the accomplished wrestler/actor’s blonde afro.

#12: Keith Hackney at UFC 3

If there was one fight to show new fans or never-watchers the wild west-like early days of the UFC, Keith Hackney vs. Emmanuel Yarborough is it.

At UFC’s third event, David fought Goliath in the Octagon and won. On one side of the cage, the 5’11” Kenpo karate blackbelt with a semi-mullet; on the other, the 6’8” and 600+ pounds of former sumo wrestler from Rahway, NJ. They say size matters, but not to Hackney who struck first with a open palm uppercut, which dropped Yarborough. Hackney tried to pounce on the felled mammoth, but Yaborough regained his wits and turned the tables on Hackney by getting his back and delivering some wallops of his own. Hackney fought back in a frenzy with Yarborough gripping and ripping Hackney’s black tanktop.

Then the bout had a cartoonish and pro-wrestling intermission as Yarborough shoved Hackney into the cage door, which burst open and sent Hackney out of the Octagon. Hackney ran back into cage, ran to his side, and, with a fire in his eyes, nodded to referee “Big” John McCarthy that he was ready for one more go around. The clash of body types resumed, Hackney hopping around looking poised to strike, itching to strike, and then - he struck.

Like a white tiger, Hackney swung his claws at Yarborough’s head; more human like, Hackney sidekicked Yarborough’s knees. The end came when Yarborough caught Hackney’s kick and reeled his opponent into, but Hackney began to blast Yarborough to the side of the head, which brought the big man to his knees. From there, a bevy of punches were delivered to the giant’s head until McCarthy had seen enough and called the mythical match-up to a close.

All told, it took Hackney a second shy of two minutes to earn the immortal nickname “The Giant Killer”.

#11: Keith Hackney at UFC 4

To the right people, the guy is an American legend. Let’s be honest, Keith Hackney’s name should be yelled from the rooftops every July 4th. Did you read the previous entry, Hackney defeated a literal giant in 1994! Three months later, Hackney scored the most devastating submission finish of them all: repeated punches to the genitals.

Technically speaking, Hackney won by a one handed choke over Joe Son, but we all know why Random Task from “Austin Powers” really tapped.

It was a different ball(s) game in the mid-90’s. Hair pulling was legal, the rounds had no time limits, actually there were no rounds, and, as mentioned, groin strikes were a-okay inside the Octagon. First thing first, how was every fight not decided by groin strikes, right? If it’s legal, wouldn’t that be everyone’s go to move? Apparently not. No one took advantage of the flimsy rulebook better than Hackney did at UFC 4.

The bout quickly went to the ground as Son tried to take the seasoned striker Hackney out of his element with an early takedown attempt. Hackney ended up on top with Son holding Hackney in a headlock. To loosen his opponent’s hold, Hackney began delivering knuckle-sandwiches to Son’s private parts. Initially, Son tried to blindly block them with his knee while trying to maintain through the pain, but after a couple cleanly landed on the family jewels, Son was pretty much done.

The legendary Hackney wasn’t done in the UFC and fought two more bouts (both losses) with one featuring a glorious flowing mullet and a wondrous failed somersault kick.

#10: Tim Sylvia s**ts his pants during a fight

It’s an incredibly unfamiliar term, an obsolete one to be exact, but it’s absolutely the most appropriate word given the WTF situation. Before the revealing the mystery, let’s take a quote from the man himself on the story’s authenticity.

“If you look at the fight you’ll see that when my shorts came down, you’ll see the wet mark in my underwear," revealed former UFC heavyweight champ Tim Sylvia to the horror of everyone forever.

To befoul one’s trousers or, in this case, one’s sponsored fight shorts. Live on free television in the main event at UFC Ultimate Fight Night 3, the world saw something horribly historic, but most likely didn’t realize it at time. The opportunity to see the infamous brownish wet stain, specifically, appeared as the 6’8” Sylvia pressed his unlucky opponent Assuerio Silva against the cage as Silva clung to Sylvia like a cat in a tree.

The seemingly unembarrassable Sylvia explained that he had been feeling ill all day and been battling a case of the “runs”. And that battle manifested itself again in the cage. While it was a fairly mundane fight that went the distance, Sylvia did take home the unanimous decision despite dueling with two very different opponents.

#9: Nate Quarry vs. Kalib Starnes

It takes two to tango and Kalib Starnes was in no mood to dance.

At UFC 83 in Montreal, the reasonable thing to do may have been for Starnes to tell his opponent Nate Quarry that he more or less had no intention of fighting that evening. Or, at least, that’s taking Starnes at his word that his lack of fight in front of his countrymen was a silent protest against the unfairness of the UFC.

There’s the other option, Quarry was too much for Starnes, frustrated him early, and when the fight was nearing a close - Starnes was more than ready for it to be over. In the first round, Quarry outstruck Starnes by landing 30 significant strikes to 2. In the second, the numbers were nearly identical with Starnes landing a grand total of 3 significant strikes to Quarry’s 29, plus “The Rock” defended a few takedown attempts. The third and final round is where Starnes and Quarry’s bout went from forgettable to phenomenal.

In the final minute or so of the bout, Starnes put his bike in reverse and began backpedaling away from Quarry with no interest in engaging. Quarry chased and chased until he saw the absurdity and decided to exploit it. At first, Quarry play-acted a running man as to poke fun at Starnes running away from him. The Canadian crowd laughed and cheered Quarry with no punch or kick from Starnes in revolt.

With no threat, Quarry finished the bout with his left hand covering his face and his right arm blindly flailing from behind it. If you’re a “Saved by the Bell” fan, it was Screech’s self-defense. Adding to the absurdity, the judges gave the decision to Quarry, but only Sensei Cecil Peoples got it right giving the bout 30-24 in favor of Quarry.

#8: Anthony Pettis wins title and no one knew it

The final fight in WEC history was a five round lightweight title fight between then champion Benson Henderson and challenger Anthony Pettis. It was 25 minutes of back and forth action exhibiting the best that this evolving combat sport has to offer and was punctuated with a last minute, gravity-defying kick affectionately known as the “Showtime Kick”. In the end, Pettis took the bout and the belt as the WEC roster was folded into the almighty UFC’s roster.

Just shy of three years later, the UFC had itself a rematch of one of the best title collisions MMA has ever known. Again, Henderson had the belt and Pettis was looking to claim it. The major difference, the first meeting was in Glendale, Arizona where Henderson lives/trains and the second meeting was set for UFC 164 in Pettis’ hometown and current residence Milwaukee, Wisconsin. The hype was quite high as the first fight was so great and Henderson had yet to taste defeat since Pettis.

As the two took to the Octagon, the highlight reel striker Pettis was greeted like he was already the champion and Henderson’s aura of invincibility was unmistakable. It was only natural to assume another 5 round war before it started, but the bout ended so suddenly the crowd didn’t have a chance to react.

After a few exchanges, Pettis got into a rhythm with some strong kicks to the body. “Showtime” went for a Capoeira cartwheel kick, which Henderson countered with a takedown and it appeared like the first round would end on the floor right there. But Pettis shot his legs up for an armbar attempt and Henderson appeared to counter it. Then Pettis let go, ran to the cage, jumped onto the cage, and celebrated while a confused crowd tried to understand that their hometown hero just won the UFC lightweight title. Even referee Herb Dean didn’t know exactly what happened.

No controversy at all, just strange. Henderson didn’t shoot up in protest. Apparently, Henderson verbally submitted and Pettis heard/felt Henderson’s arm pop.

#7: Georges St-Pierre is not easily impressed

It was either the UFC’s greatest bit of trash talk ever or the worst or the best.

At UFC 63, the boss of the Octagon’s welterweights Matt Hughes took on the only man to defeat him in five years, B.J. Penn. It was set to be a rematch of their January 2004 title fight, which Penn won via armbar. Cut to the 2006 showdown, Penn nabbed the first two rounds with the waning moments of the second stanza showing Hughes defending Penn’s submission attempt(s). Entering the third, Penn was visibly gassed or injured or something. Meanwhile, Hughes was poised to pounce and did with a takedown into side-mount with relentless punches that brought an end to another successful title defense for Hughes.

While Hughes was busy celebrating with his team and his gold belt, the UFC decided to bring Hughes’ next title rematch into the cage, Georges St-Pierre. After a quick hug between past and future opponents, Joe Rogan gave the mic to St-Pierre and that’s when he told Hughes, “I was not impressed by your performance.” DRAMA!

So benign and, yet, so cutting. Who would have ever guessed GSP would dis Hughes or dis anybody and do it like that to his face. It was a character breaking moment for St-Pierre, but his monotone, robotic delivery made it more hilarious than hurtful.

#6: Diego Sanchez’s cross

“The Dream” more like “Vampire Hunter”.

It seemed to be just your average entrance as Diego Sanchez walked to the Octagon for his main event match-up with Jake Ellenberger. The Ultimate Fighter 1 winner had an intense look on his face chugging through the bowels of the Omaha Civic Auditorium, but nothing seemed out of the ordinary until Sanchez came through the curtain and into the seated arena.

BOOM! Sanchez has a cross!

From out of nowhere, Sanchez was armed with a shiny crucifix in his extended right hand and was ready to wield it like he was Van Helsing. Add to that, Sanchez was mumbling or talking to himself or reciting a vampire curse.

#5: Bad Blood: Dana White vs. Tito Ortiz

When talking about “the” fight that never happened, many will point to Brock Lesnar vs. Fedor Emelianenko, but there’s an argument to be made for UFC President Dana White vs. former UFC light-heavyweight champ Tito Ortiz.

In all seriousness, in 2007, an exhibition boxing bout was billed between the unlikely pairing. Supposedly, it was all Ortiz’s idea and was written into his UFC contract that he would get to live out the “Fight Club” fantasy of punching his boss in the face. IN THE FACE! What may have been dreamed as a hard sparring session in the UFC’s gym during office hours became a possibly pay-per-view with a behind-the-scenes special when the Nevada State Athletic Commission said it wanted to sanction it.

That odd 90 minute countdown following around White as he worked out, lost weight, trained, and then some at 37 years old is the only testament to this unfought fight. The bout’s unfortunate end came with Ortiz no-showing the weigh-ins with no plans of it being rescheduled.

Why didn’t the boxing match happen? Maybe Ortiz realized beating up his boss isn’t the best idea or maybe the prospect of White having any success in the bout would make Ortiz lose a ton of integrity as a former champ and potential future Hall of Famer.

#4: Team Nogueira and Team Mir eating each other’s bodily fluids

The 8th season of The Ultimate Fighter took the usual prank war to an unbelievable disgusting and cringe-inducing level. Most seasons, there are a guys messing with each other’s clothes or beds or their sleep, but messing with a man’s food was verboten. That was until Team Nogueira and Team Mir entered the house.

The first team to strike was Mir’s. Apparently, Tom Lawlor had been ordering fruit platters and would often come home to find them partially eaten. The platters were the kind where the fruit are packaged in water. Lawlor and some of his degenerate teammates decided to set a trap by removing the water and replacing with their piss. And by “piss”, I’m talking about a cocktail of several men’s urine.

Spoiler alert, we watched several members from Team Nogueira eat fruit that had marinated in the other team’s pee. Later, Team Mir reveals the horrible truth to Team Nogueira.

To retaliate, Phillipe Nover mentioned that someone on Team Mir was eating the sushi roll platters he had been ordering. The degenerates on Nogueira’s team decide that someone should put a different bodily fluid on the sushi for that Mir teammate to unknowingly eat.

Spoiler alert, we watched Dave Kaplan from Team Mir eat sushi that had been laced with Kyle Kingsbury’s ejaculate. Later, they all laughed at Kaplan while UFC fans wondered, where’s the cagefighting?

#3: Wanderlei Silva wants to do what to Chuck Liddell?

Give the guy a break, it’s not his first language.

In the greatest English as a second language moment ever, “The Axe-Murderer” Wanderlei Silva told the world that he had plans of doing something a lot more lurid than trying to knockout Chuck Liddell inside the Octagon. And I quote, “I want to f*** … I want to fight with Chuck.”

GLORIOUS!

If the Freudian slip wasn’t amazing enough on its own, at the time, a lot (maybe most) of UFC fans had no idea who was the bald man with the accent was, what his Pride t-shirt was really referencing, and they definitely didn’t know why he was allowed to talk about such sexual depravities with their UFC light-heavyweight champ in the holy Octagon. So many questions for fans watching UFC 61, which Liddell didn’t even fight at.

In 2006, Silva was incredibly popular in Japan fighting for Pride and was their middleweight champ with a fan-friendly frenzied striking style, but Silva was just some random guy to those in attendance who paid to see Ken Shamrock vs. Tito Ortiz II. And not only did they not get why he had the pleasure of fighting Liddell, they certainly had a WTF moment when Silva said he wanted to F the champ.

To top it off, Silva didn’t fight Liddell when they said he would, so Silva wouldn’t be seen in the UFC for over a year as if the fateful words from UFC 61 were just a weird dream.

#2: The Upset

Frankly, there’s only one underdog Cinderella story that ever needs to be mentioned in UFC history: Matt Serra over Georges St-Pierre. No one believed it could happen and unless your name is Matt Serra or Ray Longo, you’re lying through your teeth.

At the onset of The Ultimate Fighter season 4 labeled “The Comeback”, it was explained that these former UFC fighters were getting a chance to not only win the show’s tournament and the contract, but they were also winning a shot at their division’s UFC title. The two weightclasses were welter and middle with respective champions St-Pierre and Anderson Silva waiting for the show winners.

The first winner turned title fight match-up was Travis Lutter vs. Silva at UFC 67. Weirdly enough, Lutter showed up to those weigh-ins with a shaved head and a couple pounds overweight. The extra LBs nullified the bout for the belt and it turned into your average shot at Silva. Actually, Lutter did quite well and got mount on Silva, but, soon enough in the second round, Lutter was finished by elbows while stuck in a triangle choke.

The second winner turned title fight match-up was undersized Serra vs. the then pound-for-pound best in the company, St-Pierre, at UFC 69. It was a million to one shot that the predominantly BJJ oriented Serra would be able to take the much bigger GSP down and submit him, which seemed like Serra’s only hope to analysts and fans everywhere. Strangely enough, it didn’t take long at all for Serra to walk into the Octagon and put a few fists upside the champ’s head in the most shocking knockout in the sport ever.

With the referee attending to the then former champ, Serra calmly walked away from the felled St-Pierre and did a one-armed cartwheel and proceeded to celebrate with a phenomenal amount of “oh, I guess you doubted that the little guy from Long Island could do it” faces.

#1: The man with one boxing glove

His name was Art Jimmerson.

He was a professional boxer and he was worried about protecting his jab hand. That’s the simple answer to “why?” that everyone had and will continue having each and every time they view that UFC 1 bout between Jimmerson and UFC Hall of Famer Royce Gracie. But there’s so much more to it than that because they say a picture is worth a thousand words. For Jimmerson, that picture is him with a big red boxing glove about to fight a gi-wearing soon-to-be martial arts revolutionary.

Gracie is a legend and it all started with the 6th degree Gracie jiu-jitsu blackbelt taking on Jimmerson in the quarter-finals of the UFC 1 tournament. Gracie went on to win the tournament with three submission wins that night and, funnily enough, the man with one boxing glove lasted the longest, was finished by the least, and never once threw a punch with that one glove.

Jimmerson didn’t know what he was getting himself into. It was a bare-knuckle match and that made him worry about protecting his money making lead hand for his boxing career. The right hand he left free with just some tape around the wrist because Jimmerson did understand that there could be grappling. But “One Glove” didn’t know any grappling and that showed immediately.

Gracie got the fight to the ground fairly quickly with some probing front kicks followed by a tackle takedown. Gracie went right into side control, which no doubt Jimmerson didn’t know the name of let alone how to escape from it. Gracie moved to mount, Jimmerson tried to get up, he couldn’t, Gracie hit him with a couple palm strikes, Jimmerson tried to get up again and couldn’t, so Jimmerson tapped.

End of fight, but the beginning of countless conversations about the UFC starting with, “Remember that guy who had one boxing glove? What the eff was that about?”