The Absolute Best And Worst Dessert Challenges We've Seen On Man V Food

Between hosts Adam Richman and Casey Webb, a whole lot of ice cream and sweet treats have been eaten on food travel show, "Man v. Food." In fact, just one challenge typically consists of enough food to satiate the sweet tooth of a whole family. All of the challenges on "Man v. Food" may look tasty to begin with, but that doesn't mean they remain so after one man takes on the family sized portions. We've taken a look back at all of the "Man v. Food" dessert challenges, and have determined the best and worst of Richman and Webb's sugar-filled endeavors.

Before we get into it, "worst" and "best" can be completely subjective. Here, "worst" simply means we find the challenge to be less impressive, especially considering the proven capabilities of the big eaters. We've based our level of impression on the overall creativity and realistic ability of a challenge along with the challenger's execution. No matter where a challenge falls, Season 1 through 4 saw Richman take on some monster sweets and Webb has been crushing desserts since Season 5. The best and worst of the desserts they've dared to dive into can be found below.

Spoiler alert: this challenge ended with Adam Richman yakking in a can. Crown Candy Kitchen's five malt or milkshake challenge is an oldie, and a baddie. The challenge took place back in Season 1 and consisted of five malt milkshakes, at 24 ounces each. For reference, that's 120 ounces all together, which is just shy of a gallon of milk and ice cream. Even drinking a gallon of water is a challenge for some people!

Only 30 minutes is allotted for this challenge, which means it is quite literally designed for the puke bucket. With this a very likely outcome, the prize of a gallon of free milkshake and a t-shirt doesn't really seem worth it. However, some are arguably just in it for that spot on the Wall of Fame.

After downing an impressive amount of malt, it seemed like Richman was in the home stretch. With only four more partially filled glasses of malt left, though, his stomach just couldn't handle it. He upchucked and was promptly disqualified. One challenger claimed that the milkshake option would be easier, so if Adam had opted for a shake rather than a malt, it's possible he would not have been bested. While that is still quite impressive, the challenge's near impossibility — and high chances of ending in vomit — earn it a place in our "worst" column.

Sometimes a restaurant will pull out all the stops for a challenge, and the Kitchen Sink Challenge from San Francisco Creamery was not only riveting, but absolutely gorgeous. The name does the mammoth sundae justice, because the eight scoops of ice cream sit atop a real kitchen sink. The only way this challenge would be more impressive, is if hot fudge came out of the attached faucet.

After downing two gallons of ice cream with a whole lot of whipped cream, sprinkles, and fruit, Adam Richman was victorious. He finished the sundae, seemingly milk drunk, within the hour he was given to defeat it. Though he did seem to falter at one point, Richman pushed through with a side of fries as an unexpected aid. This was a brilliant play, as the salty fries would be something to offset the onslaught of ice cream and soak up some of the liquid accruing in his belly.

Richman earned free ice cream for a year with his success, which is a pretty awesome prize where food challenges are concerned. Maybe the most coveted of prizes, though, challenge winners also get their picture plastered on the Wall of Fame.

Milkshake challenges are among some of the very worst "Man v. Food" challenges in general, so it shouldn't be a surprise to see where this one from Chick and Ruth's Deli finished. For this challenge, Adam Richman had the belly-aching task of downing a towering six pound vanilla milkshake and a one and half pound corned beef and turkey sandwich. That's a whole lot of dairy mixed with a decent amount of meat, and if food challenges are already rough on your body, then this combination is grueling.

We can't help but think that this Colossal Milkshake Challenge is designed for challengers to spill their guts before taking home the prize. Despite this, Richman actually was able to conquer the two towers of tummy ache. He walked away with a free winner's t-shirt and his face on the Wall of Fame. His victory was likely due to the fact that Chick and Ruth's Deli allow challengers an hour to down the heaping pile of meat and tall shake. Richman looked a little green in the face by the end of the challenge, and he took a full 10 minutes to take the last two bites. If the sandwich had been any larger, he likely wouldn't have made it.

New Orleans is like a cultural oasis within the United States and the food there is both distinct and delightful. Casey Webb took on Creole Creamery's Tchoupitoulas Challenge while there and this sundae deserves a spot on the list of New Orleans foods you need to try. It's so much more than just a big ice cream sundae, it's a testament to New Orleans flavor.

This four pound bowl of ice cream sets itself apart with its size, but also the unique, Creole and New Orleans inspired ice cream flavors. While you'll find the standby, historic ice cream flavors vanilla and chocolate here, you'll also be introduced to flavors like "Creole Cream Cheese," "Nectar Cream," and "Petit Four." The uniqueness and creativity of the ice cream shop is enough to give this challenge a win, but Webb also knocked back the eight scoops of ice cream and their eight scoops of toppings like it was nothing.

Another feather in the Tchoupitoulas Challenge's cap is that it actually looks appetizing from start to finish. It was a balanced sundae, whereas other sundae challenges look like a conglomerate of melting ice cream that has been dumped on by toppings. This creole sundae was lovingly put together with seemingly perfect ice cream to topping ratios. It also didn't turn into some kind of rainbow milk soup, which is Creole miracle magic in itself.

Adam Richman's last season of "Man v. Food" saw him in the coach's chair as his pupils took on local challenges. Some were successful while others failed, but The Comfy Cow's Ice Cream Challenge ended in utter heartbreak. Adam Richman's champion eater Joseph "Burrito Joe" Nikolai finished the massive, 7.5 pound sundae just to yak it up again. Of course, he was promptly disqualified, as per the challenge's rulebook. Burrito Joe missed out on a t-shirt and his picture hanging up for all to bask in his victory.

We don't blame the guy for yakking, though, because 7.5 pounds of anything straight to the gut is devastating. However, when it's made up of just ice cream and sweet toppings, it's enough to send a person into a complete sugar coma. 15 scoops of ice cream make up the base of The Comfy Cow's Ice Cream Challenge, and that is topped with six different toppings –– not including a bunch of cherries and a not-so-healthy helping of whipped cream.

Other than being a heavy, dense sundae, there's really nothing special about this challenge. There are plenty of customization options available to the competitor, but they're basically just eating a bunch of ice cream over the course of an hour. The sheer amount of dairy warrants that hour in most cases, but after that much time, it's basically just sugary milk soup that participants are left with.

This hot and cold challenge gets some major points for creativity, originality, and an overall heartwarming quality. A pound of spicy popcorn and a huge frozen "hot" chocolate are on the menu at Santa's Candy Castle in the aptly named Santa Claus, Indiana. This imitation castle does a great job of pulling us into the North Pole. The frozen hot chocolate and spicy coated popcorn take us to Christmas morning in a strange, set-in-Indiana alternate reality.

The novelty of frozen cocoa and fireball popcorn is a refreshing break from overdone sundae challenges and sickly sweet oversized desserts. Casey Webb had to eat an entire bowl of flamin' hot popcorn and a tall tower of frozen hot chocolate, topped with about 6 inches of whipped cream. Luckily, he had an hour to do so. Sporting a milk mustache and Cheeto fingers, he reigned victorious after 42 minutes of hot and cold whiplash. Once you add in the image of a very realistic Santa Claus watching over the event in the crowd, this challenge has the makings of a top tier fever dream.

When Webb did it back in 2017, he was one of only five people who had conquered the Fire and Ice Challenge. After his win, his photo went up on their Wall of Fame.

Casey Webb tackled a massive chocolate cupcake topped with layers of whipped cream in Season 6, Episode 13 of "Man v. Food." While the cupcake was certainly huge, the originality of the challenge is up for debate. Fans in the episode's comment section on YouTube claim the cupcake is made possible by a popular novelty mold. This is a little disappointing compared to a lot of the creative and original food challenges on the show.

Webb destroyed the massive chocolate cupcake, which was like eating 22 regular cupcakes, and was still able to stand up to gloat afterwards. Considering this, it's safe to say that this was one of the easiest "Man v. Food" challenges to date. He received a t-shirt for his victory, and, naturally, a photo on Kirby's Wall of Fame.

Sadly, challenger hopefuls will be disappointed to hear that Kirby's Kupcakes closed for good. As there are similar or identical cupcake molds out there, though, you could technically recreate the challenge at home. Just pop some cake mix into the massive mold and pipe a couple thick ropes of icing around the result, and you've got yourself one Goliath Cupcake Challenge to feast your face on.

It's always refreshing when a food challenge is based on amazing, made-fresh food, and Betty's Pies is known for its tasty homemade pies. Casey Webb headed to Duluth, Minnesota for a smörgåsbord of pie in Betty's Pig Trough Challenge. Three slices of pie, a banana, four scoops of vanilla ice cream, and a ton of toppings make up this calorie rich challenge.

Half a pie and what is essentially a large banana split actually doesn't sound like a lot for this big eater, considering some of the food we've seen the "Man v. Food" host put away. The real challenge here is in the time limit. Webb only had 20 minutes to defeat the Pig Trough, and he did it in just under half of that. Webb walked away with a t-shirt and a darn good dessert, featuring Betty's Bumbleberry, key lime, and lemon angel pies. That's right, the challenge allows for participants to choose their own pie flavors, of which Betty's has many.

Betty's Pies offered up a somewhat humble challenge that featured delicious, quality food with just enough hurdles to make it interesting. For that, the Pig Trough Challenge earned its place on the side of "Man v. Food" bests.

Yet another ice cream challenge had Casey Webb's brain freezing. Despite this, he did come up with a solid strategy to sink the Titanic, focusing on the cones while the hot fudge melted the ice cream below. He came out victorious, but we're questioning if the win was worth the ice cream soup he slurped to get there.

Justine's Ice Cream Parlour's Titanic Sundae shouldn't be confused with the same-named sundae Adam Moran went up against in one of Beard Meats Food's easiest challenges. Justine's is located in Ocean City, Maryland and consists of eight large scoops of creamy ice cream. The sundae is topped with four cake cones, a whole bunch of whipped cream, and six toppings of the challenger's choice.

The problem with this challenge isn't the sand castle bucket that it comes piled into. Instead, it's the exorbitant amount of toppings the challenger needs to eliminate before getting to the ice cream. By the time one reaches the middle of the bucket, you're left with a melted mess. This is especially true if the competitor chose different ice cream flavors for all eight of their scoops. Justine's offers over 20, and with all the toppings, that's just a lot of sugary flavors melding together.

Casey Webb took his crew and sweet tooth to Sota Hot and Cold in Minnesota for an ice cream topped stack of crêpes. These three massive crêpes act as a charcuterie board of desserts, with rolled ice cream, fresh fruit, whipped cream, and dessert biscuits strewn on top. Most diners would be full from just the fruit toppings, as there are about three cups of fruit, including mango, kiwi, and a mix of berries.

Webb was unable to eat the dish in under the allotted 20 minutes, but three huge crêpes plus 25 rolled ice creams is an enormous ask. Rolled ice cream is more dense than regular ice cream, so there was more to this challenge than meets the eye. We don't know how much fluffy, regular ice cream these 25 rolls would be equivalent to, but we'd wager that they would put some of his other sundae challenges to shame.

If you had your heart set on taking on this hot and cold challenge, you'll be sorely disappointed. Sota Hot and Cold is now permanently closed, so you'll have to scrape this challenge together at home if you want to try it. 

Casey Webb won this massive key lime pie challenge with two minutes left on the clock, but at what cost? A 3.5 pound of key lime pie sounds like heaven in theory. However, this dense block of pie is actually the kind of challenge that would have key lime pie fanatics never wanting to touch another slice again.

Season 8 took Webb to The Fish House for this dense challenge, where the normal sized pies actually look amazing. The meringue of the challenge version is made up of around a dozen egg whites and has to be completed in 30 minutes or less. Needless to say, it's far from "a piece of pie" to complete. In fact, according to an employee at The Fish House, Webb was the first and last person to take on this challenge. It was solely offered for "Man v. Food," but luckily the delicious, homemade pies are still available at the restaurant in Key Largo — including slices of key lime.

Another mark against this tart, texture nightmare of a challenge? The reward was akin to a slap in the face, as Webb earned yet another slice of pie. Thankfully, he also got a t-shirt out of the endeavor.