On last week’s episode of the Challenge Total Madness, Jenna Compono pulled off a massive upset win against Tori Deal in elimination. Most expected Tori to win because Jenna had problems at home and seemed mentally checked out. Fans who do not care for Tori were quick to make fun for her over-eagerness to jump into elimination with the weakened version of Jenna. While Tori continued to state that she didn’t think the win would be easy, it never felt 100% genuine. Despite Tori’s nervous exterior, there was still a feeling of overconfidence coming from her. Is it one of the Top 10 Most Overconfident moments in the shows history? Nope. However, I got the list and some honorable mentions, so let’s go through some Challenge history.
CT throws himself in against Jay (Total Madness): I think this is more CT underrating Jay’s savvy. All the guys viewed Jay as the lay-up, not just CT.
Georgia’s early presence (War of the Worlds): The expectation that her friend Nicole Bass would get safety because Georgia was a strong player immediately put a target on Georgia and actually got her thrown into the first elimination.
The Young Bucks: Existing. I cheered for them during their peak, but it’s true.
10 Wes calling a house meeting — Battle of the Seasons
On Battle of the Seasons, Wes knew he was going into elimination as his team had got voted in. He then chose to call a house meeting to declare himself the king of the game, essentially. It resulted disastrously. Wes proceeded to face Big Easy in elimination, and as we all know, Big Easy used Wes’s head to ring the bell in Hall Brawl.
The pure bravado of calling a house meeting when you’re at a low point in a game immediately only makes me love Wes more. Win or lose; he makes for great reality television.
9 Dee calling out DaVonne into elimination — War of the Worlds 1
I started with Wes and am going to follow up with his protege. On War of the Worlds 1, Dee picked DaVonne for elimination, stating that DaVonne would be the easiest win. When you consider Dee’s other options were cardio beast Georgia, 6' tall Mattie, and her best friend, Ninja, DaVonne was the best choice. However, she did not need to say it out loud with such confidence beforehand.
Then the elimination happens, and DaVonne wins. I don’t think DaVonne is a better player than Dee, but she definitely served a giant slice of humble pie to Dee at that moment.
8 Bananas ridiculous reaction to getting throw into elimination — Exes 2
One of the weirdest things about Bananas getting crazy upset over Sarah throwing him into the final elimination is in no world should he be surprised by it. The level of over-confidence you need not think you’re getting thrown or to be shocked by it is idiotic. Choosing to vote in Jay & Jenna or Bananas & Nany into a final elimination against a powerhouse physical duo of Leroy & Nia, not putting in Bananas/Nany would get put on a Top 5 Dumbest Moves in a Challenge History list.
Yet, Bananas assumed his alliance with Sarah and his aura as a legend would keep him safe. It did not, he lost his elimination, and was butthurt over it (seemingly to this day, even after stealing money from Sarah).
7 Ninja “The Climbing Expert” — War of the Worlds 2
Edit: There is some controversy regarding this entry. TJ Lavin had said on the Right Reality Podcast regarding them elim: “She was beating Ninja fair and square. Straight up, she beat the shit out of Ninja on that challenge, there’s no doubt about it. It’s just, she missed the hole and she didn’t own it.” However, there are some confliciting notes regarding this elimination that it seems like TJ may not be telling the truth or misremembering what happened.
A weird moment because Ninja technically won this elimination. It is rumored that Ninja kept telling people beforehand that she’s going to dominate Laurel if climbing is involved (climbing is Ninja’s expertise). The elimination was players climbing up a giant pole with the different rungs where they would insert pegs into holes. What happened? Laurel out-climbed Ninja and lost because she missed one of the holes and placed one of her pegs in what was not a hole. To add insult to injury, TJ Lavin blew the horn, thinking Laurel had won as well.
Due to this, Ninja got the win. Laurel was a bit over-brazen with her celebration. However, you can’t get mad at her when TJ BLEW THE HORN. Nonetheless, Ninja’s behavior before the elimination and then her actions/attitude after the elimination rubbed many the wrong way.
6 Hunter “Who Can Beat Me?” Bus Fight — Invasion of the Champions
On Invasion of the Champions, Hunter and Shane began fighting as Shane called Hunter out as a snake, partially to distance the Lavender Ladies from him and guarantee they would vote Hunter out before Shane. I understand the move since Amanda’s #1 was Nelson, and that wasn’t changing. Ashley’s #1 was Hunter, and he saw an opportunity. Shane’s move did not work, but while fighting with Hunter, it got Hunter to yell in the bus ride home from the club: “WHO CAN BEAT ME? WHO HERE CAN BEAT ME?” Hilariously, CT raises his hand in the background and points to himself, unbeknownst to Hunter.
A couple of episodes later, Hunter gets taken out by a simple sudoku puzzle where he gets beaten Cory Cheesy Pasta Wharton and Nelson Ordacity Thomas. All it took to beat Hunter was a 3rd-grade puzzle.
5 Tony Time runs out during the Final — Vendettas
Tony’s entire Challenge career reflects a crazy amount of over-confidence. Whether it is getting torched in eliminations, or stumbling in heights challenges, Tony has been humbled a ridiculous number of times in his Challenge career with a small amount of highs (there are some great highs!).
Vendettas was the season where it felt like Tony was finally breaking through as he came in with a new physique, was suddenly good in the daily challenges, and dominated the political aspect of the game alongside Zach. With near 40k dollars in his individual bank account, Tony assumed the final would be Tony Time. He then quickly realized a Final is much harder than he ever expected (the Vendettas final was 40% as tough WOTW 1 Day 1). Tony did not manage his cardio well, fell to last place among males immediately, and got purged out of the game with no money to show from the season.
4 Paulie’s Purge Performance — War of the Worlds 1
Right before Paulie performed in the final purge of War of the Worlds 1, he looked into the camera and said he was not only going to be in the final, but he was going to set the best time out of anyone in the challenge.
Paulie then proceeded to wipe out multiple times in grand fashion (none of the other males fell once). The guy killed numerous daily challenges, won a crucial elimination earlier in the game, and then he drank too much of his own kool-aid and flopped with the stakes at their highest. It’s okay; he totally redeemed himself with War of the Worlds 2 final performance!
3 Jordan’s Chirps at Johnny Bananas — Free Agents
This next one is an amalgamation of moments from Jordan on Free Agents. Jordan expected to become King of the Challenge following his strong rookie performance on Rivals 2. He kept gunning after Johnny Bananas and taking shots at him and his abilities. When Johnny beat Isaac in Balls In, Jordan said that the win doesn’t matter if it’s not against him. Yet, the following week, Jordan was beating his chest like he won the Super Bowl after beating Swift in an elimination.
Jordan then played the boldest move by getting his friend Johnny Reilly to put Bananas in elimination, where Jordan would pull all the kill cards and face Johnny in elimination. I do give props to Jordan for going through with the move since he knew the elimination was Wrecking Wall, and he’d be at a disadvantage. Nonetheless, Jordan has to be on this list.
2 Sarah Rice is really good at puzzles — Rivals 1
On Exes 1, Sarah Rice was extremely confident that she and Kailtyn would defeat Jasmine and Jonna in their elimination, especially if the elimination was Sarah’s specialty, puzzles. Sarah is one of the best players in Challenge history; I’d probably rank her in the Top 10 regardless of gender. Rivals 1 is not a shining moment for her. In an elimination that was a simple puzzle that you would play at a Cracker Barrell, Sarah made a massive flub early on, whereas Jonna had her beat from the start.
Jonna, a player who would struggle with multiple puzzle and memory challenges going forward, defeated “Puzzle Expert” Sarah Rice. It’s similar to beating Wes in a swim, Darrell in an endurance comp, or Nelson in a mispronunciation battle. People who hate Sarah are always going to use this moment against her, and then when you add that she was so confident in the house going in, it only adds insult to injury. It was the last time Sarah got eliminated on a Challenge.
1 Wes guns for Cohutta — The Ruins
Yeah, Wes made this list two times. Honestly, we could put him on this more, put two suffices. Wes is both a character and a competitor, and oh boy, some of those early Wes seasons are chocked full of unfiltered confidence and testosterone. Modern Wes is confident in a more machiavellian or evil cartoony fashion. Ruins Wes is a douche-nozzle mixed with the resume of what was either 2nd or 3rd best competitor in the show’s history, to that point. He was the first individual male champion, carried Casey Cooper to a Final, and had an 8–0 elimination record.
On the Ruins, Wes did not like Cohutta because he was not happy with how friendly Cohutta was with KellyAnne (Wes’s current GF). Even though Cohutta was interested in Susie romantically, Wes immediately decided he did not like Cohutta, and his goal was to take him out. Since Wes knew he was likely going into elimination, he took his shot at Cohutta after the fifth daily challenge, declaring himself a mercenary. He then had smarmy confessionals where he feigns remorse about taking Cohutta’s girl and taking him out of the game. What happens? Cohutta torches Wes in their elimination and sends Wes on a downward spiral that he legitimately doesn’t fully recover from for about five years. Cohutta slayed the King, got to make out with Susie, and got cemented in Challenge history as a legend. Wes then became a humble person. Not.