Reality television is known for having moments that go viral. Thanks to YouTube and social media, when something major happens on a reality show, you can bet the world will be talking about it for years on end. The Challenge has had some insane moments throughout its 40 seasons. From massive game moves to legendary competition moments, The Challenge has provided a handful of WTF moments that we can’t get enough of.
The Challenge has been a major reality television program since 1998. Evolving over the years, the show originally invited cast members from The Real World and Road Rules to compete in wild challenges for cash. Over the years, new players from other intellectual properties were introduced into The Challenge. No matter who competed, The Challenge has never been short of WTF moments. Here are some of the best of the best moments throughout the history of the show.
The Challenge
- Release Date
- June 1, 1998
- Cast
- T.J. Lavin , Cara Maria Sorbello , Johnny ‘Bananas’ Devenanzio , Aneesa Ferreira
- Main Genre
- Reality
- Creator(s)
- Jonathan Murray , Mary-Ellis Bunim
10 Aneesa Has Yet to Win a Challenge
Various Seasons
Aneesa Ferreira made her MTV debut as a roommate on The Real World: Chicago. Following her run on the show, she made the leap over to Real World/Road Rules: Battle of the Sexes, where she began to solidify herself as one of the faces of the series. She was a halfway decent competitor, she lived for the drama, and she was never shy of fighting for a win. And after competing in nearly 20 seasons on the flagship program as well as the various spin-offs, Anessa has never won. She’s essentially become the Susan Lucci of The Challenge.
Anessa has made the final challenge on The Gauntlet 2, The Duel II, Ride or Dies, and The Challenge: All Stars 1. But she continued to come up short. Hell, there have been seasons when some of her fellow competitors have tried to honor her and help her net a victory, but she just simply cannot get TJ Lavin to call her a champion. At this point, Anessa is one of the most deserving individuals. She’s put in her time and has helped to define the program. At some point it’s gotta work out for her. Right?
9 Cooke Has an “Accident” in Elimination Pool
The Challenge: Rivals II
The Challenge is usually known for the high-stakes drama, fights, and competitions, but sometimes, some comedic moments are just too good not to make it to air. One of those instances occurred during The Challenge: Rivals II. When the season started, Heather Cooke was originally paired with Naomi Defensor, her The Real World: Las Vegas roommate. But after a family emergency caused Naomi to have to depart, Cooke was assigned a new partner she had never met. It was Cara Maria Sorbello, and they were a formidable pair.
They were put into elimination where they were set to face off against The Real World: Portland rivals Anastasia Miller and Jessica McCain. Anastasia was having a bit of a panic attack-slash-fainting-spell prior to the start of the elimination and was having the production team look after her. Well, with the mechanics of the game already placing Cooke and Cara in their contraption, Cooke had a little bit of a bathroom emergency and needed to relieve herself. So she took a tinkle, right in the pool. It was a comic moment during a tense situation; and even if the show is high drama, there is a lot of fun that happens on the side.
8 Ashley Steals Hunter’s Finale Money
The Challenge: Final Reckoning
The Challenge loves to push their players to their limits. So, when the opportunity arises to implement chaos and pair players with people they loathe, The Challenge will most certainly do so. In the final chapter of a series of seasons, The Challenge: Final Reckoning paired up enemies and rivals as they were forced to work together to earn one of the biggest cash prizes in Challenge history. This season was filled with a handful of twists, one of which allowed Hunter Barfield and Ashley Mitchell to enter the game later in the season. Their challenge prowess got them to the end, but it was a rocky road.
For the final challenge, there was a time aspect that, despite working in teams, the players had a clocking ticking that would result in a massive decision in the end: the Millionaire’s Dilemma. Ashley and Hunter ended up landing in first place, but with Ashley having the faster time, she was able to decide whether she wanted to split the prize with her partner or keep it all for herself. Well, don’t mess with a woman scorned because karma is a you-know-what. Ashley decided that, due to the way she had been treated by Hunter and his allies, she was not going to reward him. She took the money. Fans could understand her perspective, but it will forever be considered a savage move.
7 Killa Kam’s Master Plan
The Challenge: Final Reckoning
With all the twists and turns that The Challenge throws at the competitors, sometimes it’s hard to figure out the game as it changes each time you play. But when you figure out a way to hack the game, you become a legend. Kam Williams became a legend when she concocted a brilliant plan during The Challenge: Final Reckoning. Only, she couldn’t have her glory because TJ Lavin had a plan up his sleeves. The way that The Challenge: Final Reckoning worked was, teams secretly voted one of the losing pairs into the Armageddon elimination round. Kam Williams was paired up with Kayleigh Morris after their original partners were sent packing for a physical altercation. She was eager to secure her place in the game and was ready to manipulate everyone in the process.
Killa Kam came up with a brilliant plan. Having won the daily challenge alongside Kayleigh, she announced her intentions to vote for Kyle Christie and Brad Fiorenza or Joss Mooney and Sylvia Elsode, which shocked the house as Sylvia was her close friend. But it was all a ploy and part of her master plan. So the house came together to implement burn votes so the only votes that would matter would be Kam and Kayleighs. Everything was about to work out according to plan. That is until TJ was like psyche! TJ introduced Hunter Barfield and Ashley Mitchell as Mercenaries and ended up earning a spot in the game. Sadly, this one major twist would help aid in Kam’s downfall, but what a different outcome this season could have had if Kam’s plan worked out.
6 Belou Brings Her Baby
Real World/Road Rules Challenge: Battle of the Seasons
The early seasons of The Challenge, or Real World/Road Rules Challenge as it was called then, was a completely different beast. It was a celebration of fun and silly games that united the best of the best from The Real World and Road Rules. The season that truly changed the course of the series was also one of the most underrated seasons in the franchise: Real World/Road Rules: Battle of the Seasons. While it was still The Real World vs Road Rules format, the cast was divided into teams of two that united cast members from their original franchise. Between the introduction of the Inner Circle, having Mark Long and Eric Nies as hosts, and the crazy drama that ensued, Battle of the Seasons was so much fun.
Filmed in Cabo San Lucas, Mexico, you would think that the wildest moment of the season was either the timely nickname that Beth Stolarczyk was given or the filming-pausing hurricane. The biggest WTF moment came from former Road Rules: Europe castmember Belou Den Tex…who brought her baby to the child. Yes, that’s right. An infant. In the Challenge house. Based on how the show is today, it would never fly, ever. But 2002 was a different time. Belou and her partner Chris Melling only lasted three episodes, but Belou’s baby made a lasting impression.
5 Vets Lose Due to Big Easy’s Collapse
Real World/Road Rules: Gauntlet III
Forcing a group of rookies to battle a bunch of veterans just didn’t seem quite fair. But that was the format for Real World/Road Rules: Gauntlet III. The veterans squad was completely annihilating the rookies. When a veteran was ultimately sacrificed, it was because they saw them as weak or a liability in the final challenge. Oh, and if they were all good pals with an alliance, you would be safe. Such was the case with Evan Starkman, Kenny Santucci, and Eric “Big Easy” Banks. The trio were good pals from Real World/Road Rules: Fresh Meat. They had quickly become the new faces of the program. And they wanted to celebrate their friendship by winning a challenge together. Only when they reached that final challenge, host TJ Lavin had some rules and stipulations for the final challenge.
The final challenge was called the Army Strong Final Challenge. TJ made it quite clear that all team members must cross the finish line in order to win. The final featured a bunch of the challenges seen during the season at checkpoints. It was a fairly straightforward challenge. The only hitch was that the Army Strong mentality featured all the team members chained together. You are only as strong as your weakest link. And for the vets, their weakest link was Big Easy. Literally. In the middle of the challenge, Big Easy passed out. He was being dragged by his teammates until they had to stop. On the ground, his eyes almost rolled in the back of his head. He had to be removed from the group to receive medical attention. The vets lost their weakest link and finished first. Until they were reminded that all teammates had to finish. Without Big Easy, by default, they lost, and the rookies won the season. This moment forced all future players to truly think of the big picture in the end as they competed during the season.
4 Good Guys Brad and Darrell Fight
Real World/Road Rules Challenge: The Ruins
Throughout their tenure on The Challenge, Brad Fiorenza and Darrell Taylor were considered reasonably good guys. They were incredible competitors and genuine people, but the stress of competition can sometimes get the best of people. For these two, it certainly did. During Real World/Road Rules Challenge: The Ruins, the passion and desire to win overshadowed smart decisions. The season was split up by champions and challengers, for which Darrell was a champion and Brad had yet to win. And Brad was eager to finally win a season.
With frustration pervading the air, some innocent banter among friends led to an unfortunate fight that resulted in both men being forced to leave the game. Darrell, an experienced boxer, knocked Brad to the ground and continued to pound him. Brad was completely knocked out and had a swollen eye to prove it. Despite being remorseful and regretful for this unfortunate incident, the rules are the rules, and they were disqualified for competing in this season.
3 Julie Tries to Kill Veronica
Real World/Road Rules Challenge: The Inferno
The mantra of “do what it takes to win” has limits. Such was the case during Real World/Road Rules Challenge: The Inferno. Julie Stoffer would consider her actions by doing whatever it takes to win. Others would consider it attempted murder. Julie was already a target on the show because of her previous beef with the OG Mean Girls of the show. Julie was a competitor, a major trait and flaw that often got the best of her.
During a zip line challenge, Julie knew that The Real World team needed a victory, so she was determined to ensure it would happen by any means necessary. Unfortunately, she took things too far when she began to sabotage Veronica Portillo‘s performance by messing with her safety harness. Julie was not listening to the pleas of Veronica or the other competitors on the other side of the building. She had one mission in mind, and that was to win. In the end, the heat was called. This was easily one of the scariest and jaw-dropping moments in the history of the show.
2 Bananas Backpack
The Challenge: Cutthroat
Johnny Bananas and CT Tamburello are easily two of the most infamous contestants to ever step foot on The Challenge. They have had two very different journeys on the show. For Bananas, he went from a good guy to a diabolical villain. For CT, he went from a bad boy to a humble man. After punching two cast mates in two separate seasons, CT hadn’t been back on the show in a few seasons. His presence was missed, but other competitors filled the void. One of which was Johnny Bananas. Bananas became a mastermind from a political perspective, as well as one of the strongest physical threats. But that would all be put to shame in a shocking elimination challenge.
On The Challenge: Cutthroat, TJ Lavin introduced a shocking twist where the two players in the Gulag would not go head-to-head but against a Heavy Hitter. For the men, that Heavy Hitter was the triumphant return of CT Tamburello. CT had cooled off as a person, but he was eager to prove he deserved to come back. And this performance in Back Up Off Me was exactly what it took. In the challenge, Bananas and Tyler Duckworth had to compete against CT and whoever had beaten the beast or had the fastest time would win. Something overtook CT because when that horn sounded, the man slaughtered Bananas, carrying him like a backpack as he stomped on the barrel, tossing him straight into it. It will forever be one of the most dominating single performances the show has ever seen.
1 Bananas Steals Sarah’s Finale Money
The Challenge: Rivals III
Johnny Bananas was not the greatest of guys the longer he remained on The Challenge. But he solidified himself as the biggest villain in the history of the show when he shocked the world with his shocking decision. In the third part of The Challenge: Rivals series, the men and women were paired up with individuals they had an intense history with. For Bananas, he was paired up with Sarah Rice. She was an incredible competitor but became his rival almost by default. Well, she did nominate him for the final elimination during The Challenge: Battle of the Exes II.
Even though they were paired up, Bananas had a grudge. Bananas and Sarah were easily running away with the season. They were going to win as a team. And they did. But in TJ Lavin’s final challenge, there was a twist. There’s always a twist. Throughout the various checkpoints in the final challenge, the players earn points. And those points played a major factor in the final result. Bananas earned more points than Sarah and thus had the option of splitting the money or taking it all. Bananas, with a smirk on his face, walked away with all the money, leaving Sarah with nothing but disbelief. It was a shocking and vile move that fans still can’t get enough of.
