The Funniest Man V. Food Mishaps

When "Man v. Food" premiered on the Travel Channel in 2008, it sought to answer one very important question: just how much can one man really eat? Its original host, Adam Richman — and his successor, Casey Webb — shone a new spotlight on the world of competitive eating, as each man tried to complete some of the craziest food challenges that U.S. restaurants have to offer.

Inevitably, not all of these challenges go to plan. As its name suggests, each episode of "Man v. Food" truly is a battle between copious amounts of food and the limits of the human appetite and body. Sometimes, even the strongest of stomachs are no match for a 190-pound burger or a 72-ounce steak. Over the years, food has got the best of both Richman and West, leading to some hilarious mishaps that have been caught on camera for audiences to watch over and over. Here are some of the funniest moments "Man v. Food" went sideways.

Of all the foods to overwhelm Adam Richman during his time on the show, milkshakes at first seemed to be the most innocent. While visiting Crown Candy Kitchen in St. Louis, Missouri, he was challenged to take on one of the oldest food challenges in the country that just over 50 people have achieved in the past century: drinking a whopping 15 malt shakes in less than 30 minutes.

It should come as no surprise that this feat quickly proved to be more sickly than sweet. Richman soon found himself swamped by the sheer amount of sugar and dairy in the beverage. Even though he got to choose the flavors himself (he opted for vanilla, eggnog, coffee, and a chocolate-coffee mix), and implemented a tactic of mixing each shake so it had a thinner, more milky consistency, it became increasingly tough for him to swallow each beverage.

With just four drinks to go, nausea got the better of Richman, who then had to hurry to the bathroom. Not only did this mean he was disqualified, but the episode had to be censored and adults rather dramatically covered the eyes of nearby children as the milkshake decided to make a reappearance before Richman could make it to the toilet. All told, it was a win for milkshakes and a loss for Richman's stomach.

One of the most infamous moments on "Man v. Food" happened in Sarasota, Florida, where Adam Richman took on Munchies 4:20 Café's Fire In Your Hole Challenge. This involved finishing 10 chicken wings drenched in an über-spicy sauce made of habanero pepper, hot sauce, cayenne, crushed red pepper, and the extract of the infamous ghost pepper, certified to be 170 times hotter than Louisiana-based Tabasco sauce.

Eating 10 wings covered in this hellish concoction with only small sips of water to keep him sane ended up being easier said than done. Richman — who's usually pretty unflappable when it comes to spicy foods — ended up bailing out of the challenge after just two wings, fleeing to the walk-in freezer with a glass of milk in hand.

It was later revealed that Richman was set up to fail. In a 2017 appearance on Hot Ones, he claimed the cafe sabotaged him by using an entire bottle of ghost pepper extract. Richman was less upset about the loss than the potentially dangerous methods used to make it happen. As he explained to host Sean Evans, the wings (which reportedly used some of the same ingredients found in police grenades) caused his tongue and nostrils to swell by the time he made it to the bathroom. "The reason why I'm mad is not because of my record," Richman said. "I don't give a s*** about that. It's that it's cavalier and dangerous."

Milkshakes once again threatened to be Richman's downfall during the Colossal Challenge at Chick & Ruth's Delly. Tasked by the Maryland diner with consuming a 6-pound vanilla milkshake and a 1.5-pound turkey and highly salty corned beef sandwich in less than an hour, he dove straight into the milkshake without a straw — only to get blindsided by a brain freeze as the blood vessels in the roof of his mouth began to constrict.

"Right now it's too cold to go on," Richman admitted, rapidly stirring his shake. "I've got a little bit of brain freeze right here. I'm gonna let this melt for a little bit, work on the sandwich for a bit."

Fortunately, it was only a minor setback. An undeterred Richman waited for the epic brain freeze to subside before trying a new strategy –  chewing a little bit of sandwich, followed by a few sips of shake, then a few more bites of the sandwich, and so on. It ended up being a winning approach, as Richman not only beat his competitor and self-proclaimed local milkshake enthusiast Heather (who bowed out before she even touched her burger) but managed to beat the challenge with just 10 minutes to spare — becoming only the third person out of hundreds to attempt so.

Spice led to another of "Man v. Food's" most iconic mishaps while Adam Richman was filming season four in New Mexico. Midway through his opening monologue in an Albuquerque field, Richman fell foul of that voice in your head that encourages you to act upon your wildest impulses — fearlessly biting into a pepper that ended up being much spicier than he expected.

After a beat of silence, Richman threw his head back in horror as the spice set in. As is the case with practically all his spice-related challenges within the show, he managed to handle the fiery kick pretty well — but judging by the look on his face, his shaking hands, and the desperate, silent "Why?" he lobbed to the sky, he still suffered pretty badly for this particular mistake. Sadly, it seems as if the Travel Channel decided against using this take in the final version of the episode, but at least they were kind enough to share the outtake online.

There's spicy food, and then there's food that is so mind-numbingly spicy it stings your fingers as well as your taste buds. In the Hellfire Challenge, Adam Richman encountered food that very much falls into the latter category.

Not only did he have to eat all 12 of the fiery hot wings presented to him at San Jose's Smoke Eaters Hot Wings — each coated in a made-to-order sauce that contained the equivalent of six habanero peppers — but he specifically had to do so sans gloves so he could lick the sauce from his hands once he was done. Yikes.

Halfway through the challenge, Richman appeared to be suffering so much that it looked like he was in the midst of an existential crisis. In his own words, "each finger was like licking fire. But then the torture really began: five minutes of waiting. No relief, only time." Once he'd gnawed each wing down to the bone, he was forced to sit through an "afterburn" period where he was banned from washing his face or hands or drinking water. "With nothing to soothe my molten mouth, I drifted to the very brink of unconsciousness," he claimed. Entertaining for us to watch, sure, but it appeared to be absolute torture for Richman to experience.

The meat sweats get the better of all dedicated carnivores at some point — especially if you're trying to devour an 8-pound grilled sirloin steak. While visiting Puerto Rico, Adam Richman attempted to do just that as a part of Vaca Brava's Vaca Acosta Challenge (also known as the Sleeping Cow Challenge), which gave him 40 minutes to finish his steak as well its accompanying mountain of fries, bacon, mushrooms, onion, gravy, and Parmesan cheese.

This kind of meal doesn't go down too easy, especially when combined with the humid, sticky Caribbean climate. It all became too much for Richman, who had to temporarily pause his efforts to dry off with some paper towels. This wasn't just a comfort issue, either, as Richman found himself losing so much water from his body that he struggled to find the saliva necessary to swallow his food (which is kind of key in an eating competition).

While Richman managed to shake off the meat sweats, he struggled to get back on track. While he ate most of the steak, he only finished about half of the fries. So dire was the situation that he even admitted that if he'd ever given any serious thought to becoming vegetarian, this was the time. In Richman's words, "The meat sweats are so, so real."

When Richman decided to retire from competitive eating in 2012, Casey Webb stepped in to take his place. The new host of "Man v. Food" proved to have an appetite just as powerful as the last — but even he has found himself in some sticky situations during his tenure on the show.

After heading to Allan's Authentic Mexican Restaurant in Portland, Oregon, Webb took on the Diablo Burrito Challenge — the name given to the task of downing a 2.2-pound burrito filled with 10 of the hottest chili peppers in the world. Unsurprisingly, this was no easy feat. Despite diving in with a strong strategy to start by eating the two serrano "horns," these proved to be so spicy that Webb was hit by a stubborn bout of what may be the least dignified way to duck out of a challenge: hiccups.

These only got worse as Webb tried to power through the burrito (which he described as tasting "like if lava had a flavor") itself. Although he managed to finish half of the burrito in five minutes, the combo of pain and hiccups — which seemed to only get worse with every sip of water — put him at a disadvantage. Flushed, sweating, and struggling to breathe, Webb's time ran out with a third of the burrito remaining.

In case you hadn't noticed, dairy is a recurring threat in the world of "Man v. Food." It claimed yet another victory in Kentucky's Comfy Cow Ice Cream Challenge. As was the case with all of the show's fourth season, this episode saw Adam Richman take a step back from competitive eating and instead coach local recruits to win over-the-top food challenges. This time, the lucky (or, considering what happened next, unlucky) participant was warehouse custodian Joseph "Burrito Joe" Nikolai, who attempted to finish a 7.5-pound ice cream sundae comprised of 15 scoops of The Comfy Cow's famous ice cream, as well as fruit, whipped cream, and a quarter-pound of nuts. He had to down it all in just 60 minutes.

Richman's expert advice was to keep a strong pace and liquidate the ice cream as much as possible. This got Nikolai off to a good start, and he cleared a pound of ice cream in a matter of minutes without suffering from brain freeze. But sadly, this steady speed ended up being Nikolai's downfall. While he managed to finish the entire sundae and its toppings, he promptly vomited the whole thing back up — forcing the Travel Channel to cut to a screen apologizing for "experiencing digestive difficulties" – which meant that the food, not man, won the challenge on a technicality.

When Casey Webb sat down to attempt the 29-Inch Pizza Challenge (in which he had to, surprise, eat a 29-inch pizza) at Schiappa's in Lebanon, Illinois, he brought Ryan Maassen — a former champion who conquered the same challenge 10 years earlier – along for the ride. However, even the combined efforts of two stomachs weren't enough to overcome a surprisingly stubborn obstacle: cheese.

Everything started strong for the pair, but the cheese on the pizza hardened as it cooled, making it much tougher to swallow. As if struggling to force down increasingly dry crusts wasn't enough, the toppings also caused a logistical nightmare as the green peppers, onions, black olives, mushrooms, and pepperoni began to slide off each slice when Webb and Maassen moved on to the crust-free inner pieces. While they later implemented additional strategies — such as standing up to digest the food more quickly — the pair were a few slices short of finishing when their allotted 30 minutes came to an end.

Entertaining though this cheesy palaver may have been for viewers, we can't help but feel this must've been one of the more disappointing losses. Had they won, Webb and Maassen would have secured not just the standard t-shirts and comped meals, but a free pizza of their choice every month for the next year. What a missed opportunity.

Throughout his 85 episodes of "Man v. Food," Adam Richman proved himself to be relatively impervious to heat. However, a visit to Orochon Ramen in the Little Tokyo district of Los Angeles pushed him to the limits of his considerable spice tolerance.

In just 30 minutes, Richman had to finish a 2.2-pound bowl of the restaurant's Special No. 2 — a ramen soup made up of Orochon Ramen's secret spice mix and chopped jalapeños. What started as a strong attempt soon devolved into a fiery nightmare. Once Richman was done with his noodles, he downed the remaining broth and tears gradually began to stream down his cheeks. There was a moment where it looked like he was considering all his life choices. Things got so bad that someone had to step in and sponge the combination of tears and sweat off his face.

Weaker men would have thrown in the towel then and there, but, miraculously, Richman powered through. Against all odds, he managed to drain every drop of ramen, something only a few hundred participants out of 20,000 have achieved, earning himself a well-deserved spot on Orochon Ramen's Wall of Bravery.

One of "Man v. Food's" most memorable mishaps is still ongoing to this day. Back in season one, Adam Richman traveled to New Orleans, where Acme Oyster House dared him to eat a mind-boggling number of oysters (180, to be precise), a challenge that an average of five out of six competitors failed.

With the aid of some lemon and hot sauce, Richman successfully guzzled down the oysters like a champ in just 21 minutes and ended the challenge surrounded by towers of plates and empty mollusk shells. However, it turns out that the challenge didn't end when Richman left the French Quarter. Nearly 10 years after the episode first aired, Richman made a guest appearance on The Premium Pete Show, where he admitted that he's struggled to eat oysters ever since.

"After the oyster challenge in New Orleans, which was over half a decade ago, I think I may have had less than a dozen since," he revealed. "It just turned me off." Considering the sheer amount of food he consumed during his time as a competitive eater, the shocker isn't that Richman can't stomach oysters anymore, but that there aren't more foods on that list.

Adam Richman isn't just a self-proclaimed, lifelong gastronaut; he's also a diehard fan of the New York Yankees. That's what made the stakes so personal in season one's Eagle's Challenge, where he tried to chow down a 5-pound burger with 20 slices of bacon and cheese, 5 pounds of fries, and a giant pickle more quickly than his competitor. His goal: avoid losing and being forced to wear an "I Love Boston" shirt.

Unfortunately, Richman was out-eaten by former Eagle's Deli and Restaurant employee, Chuck Whittall (who, as a Boston Red Sox fan, would've been forced to wear an "I Love New York" t-shirt if he lost). Weighing their leftovers, it was revealed that Richman had eaten six ounces less of his burger and fries, meaning he had to change into his new shirt then and there. Richman didn't exactly look pleased about having to do so, but he at least begrudgingly shook his rival's hand before covering his face while taking a picture for Eagle's Deli and Restaurant's Wall of Shame.