Bracket Madness: All's Fair in Love, War and MTV's The Challenge

Tonight, MTV’s The Challenge concludes its 26th season. The show, which started in 1998 as the competitive, drunken lovechild of two MTV staples - The Real World and Road Rules - has surpassed its parents to become one of the greatest demonstrations of athletic prowess and drunken antics of all time, and, not to exaggerate, America’s Fifth Greatest Sport. In honor of March Madness, we decided to pit the best of the best against each other to determine the best Challenger. 

And what do we mean by best? It’s easy to determine who’s won the most times or the most money. (Seriously, just hit up the impressively detailed Wikipedia page.) No, we’re in it for the entertainment value! Simply put, who makes for the best TV? Of course an impressive physical game plays a key role, but we’re also looking for the greatest quips, the biggest beefs, the steamiest hookups.

When determining the most entertaining Challenger, we selected 32 competitors for our bracket-style tournament. These contestants were selected by a three-person committee cross-referencing (and arguing over) their own individual lists of worthy inclusions. 

Then, we used hard statistics to seed the Challengers. Each competitor was ranked based on the number of season appearances, total money won, number of final challenges reached, and number of elimination rounds won. The data includes seasons 1 through 25, but excludes the currently airing Battle of the Exes II to preserve our sanity. Everything was as fair as it could be during the seeding process. After that, things got messy. Here is our breakdown of the most entertaining Challenger of all time.

Round 1

The Gauntlet

1. Bananas vs. 8. Nany
It’s no fluke Johnny Bananas keeps getting calls from Bunim/Murray year after year to come back to The Challenge. He’s basically the godfather of the new era and always provides stellar moments. Nany, your feud with Theresa has been wonderful to witness, so just be happy you made it into this prestigious field at all.

4. Veronica vs. 5. Jenn
Jenn with two N’s is a welcome face on any season, but Veronica was Queen Bee for most of her time on the show. She and Rachel ran the house during their prime, lording over everyone that stepped through the door.

3. Laurel vs. 6. Mark
This was the hardest first round matchup decision because both of these Challengers clearly deserve to be recognized. Laurel is bonkers in a serial killer kind of way while Mark is bros with everyone and even co-hosted one season. But nothing can stop Laurel from winning a challenge, and nothing will stop her from taking this match-up. 

2. Brad vs. 7. Sarah
Though Brad was a staple of the middle seasons, posting several finals appearances culminating in a win (although TBH Tori’s politicking had a hell of a lot to do with that), Sarah is the embodiment of The Challenge and the frequent Mama Bear of the house. She wants to win so much but is frequently saddled with shitty teammates. At this point everybody should be pulling for her to finally get the W.

The Inferno

1. Wes vs. 8. Leroy
Maybe after putting in a couple more appearances, Leroy’s awesome chillitude could overtake Wes, and we wish it would. But Wes is as close to a straight-up villain that The Challenge has, and he always manages to stick around in spite of it. Plus, we’re always dying to hear more tidbits about Wes’s off-screen life. Let’s see that monster truck, dude!

4. Aneesa vs. 5. Mike
Mike used to be one of the better competitors during the early, more lighthearted years of The Challenge. However, he consistently relied on his alter ego, “The Miz,” to be a better physical competitor, and took it way too seriously. Aneesa is far more entertaining to watch because every action she does seems authentic. Her outbursts may be laughable, but they serve a purpose… to scare competitors and create entertaining moments.

3. Darrell vs. 6. Emily
This is just a battle of the boring. Both challengers are very good at competing, but that’s it. Emily has had a few notable moments, but Darrell’s altercations with Wes and Brad make him a marginally more entertaining person to watch. 

2. Evelyn vs. 7. Tonya
Evelyn is undoubtedly the better competitor (despite her stupid hair), but Tonya is a classic Challenge pot-stirrer, always inserting herself into mean girl drama and can be relied on to get drunk, cry, and/or take her clothes off.

The Gulag

1. Derrick vs. 8. Frank
Most fans love Derrick, as he seems like a genuinely good dude and a decent competitor, but Frank is infamous for his incessant meddling and constant drama. Audiences may love or hate Frank but either way, he gets more camera time and way more reactions.

4. Evan vs. 5. Coral 
These two are both Challenge staples. Coral is the reason that Evan’s Challenge career started, and Evan is part of the reason that Coral’s career ended. Coral wins for her capacity to play the game in an entertaining way. Evan is a follower. If he weren’t friends with Bananas or Kenny, people really wouldn’t care. Coral is the person you love to hate, and she makes great television because of it. 

3. Cara Maria vs. 6. Camila
Cara Maria gets a lot of narrative screen time and for a good reason. She’s gone from mildly incompetent social leper to an indomitable force that refuses to be eliminated no matter how many times she gets tossed in. However, that doesn’t top the terrifying magnetism of one of Camila’s alcohol-induced psychotic Brazilian breakdowns.

2. CT vs. 7. Theo
Theo was one of the best talking heads The Challenge ever had, offering insight and humor in many of the early seasons. But let’s be honest, CT brings so much to The Challenge he might as well be getting producer credit. His iconic fight with Adam on the first episode of The Duel 2 is longer than Theo’s entire highlight reel.

The Dome

1. Kenny vs. 8. Timmy
Timmy is certainly the goofiest Challenger in the show’s history while Kenny, aka Mr. Beautiful, is one of the loudest. Kenny’s jerkish attitude propels him along in this bracket, but let’s give Timmy his due. Timmy was always having the most fun, while acknowledging how absurd it all really was. 

4. Landon vs. 5. Rachel
Rachel may be a great physical athlete, but the only reason she has ever entertained us in the past is because of her friendship with Veronica. What gives Landon the edge is his underdog win during Fresh Meat 2, which left viewers feeling for the kid as he struggled to make it to the final. Landon takes this one… just barely.

3. Abram vs. 6. Katie
Katie was never viewed as a competent competitor and often had teammates trying to intentionally lose challenges in hopes she would be eliminated. Yet, that hatred only fueled her fire and she got off some spectacularly bleeped out monologues over the years. Abram is a wild man with intense energy, but only became super endearing when he was in a relationship with Cara Maria. 

2. Paula vs. 7. Diem
This is a very difficult matchup to assess. Diem, rest her soul, was a warrior. Her struggle with cancer is heartbreaking, and her relationship with CT became one of the longest story arcs in Challenge history. Though Diem was the emotional center of every season she was a part of, Paula is a far more entertaining person to watch. She embodies everything The Challenge stands for: she’s competitive and she knows how to put on a good show.

Round 2

The Gauntlet

1. Bananas vs. 4. Veronica 
Bananas embodies what it means to be an entertaining Challenger. Never admitting you’re wrong? Check. Shouting loudly and longer than anyone else to get your point across? Check. Berating other Challengers if they defy your plans? Check. Veronica has some great moments that we can remember fondly (i.e. The Gauntlet three-way and The Inferno high ropes freak out), but Bananas has better overall entertainment value. Veronica helped build the show, but Bananas brought it to new heights.

3. Laurel vs. 7. Sarah 
Sarah is possibly the competitor most devoted to the very idea and experience of The Challenge. But Laurel’s unparalleled brand of ruthless crazy definitely comes out on top. Laurel kept an honest-to-God burn book of those who had “gone against her” in one-way or another and vowed revenge on all of them. If she had a little trove of voodoo dolls using actual human hair from other Challengers, it wouldn't surprise us. 

The Inferno

1. Wes vs. 4. Aneesa 
The problem with Wes is that he doesn’t know how to make people like him. He won’t hesitate to throw his best friend Danny under the bus to stay in the house one more week, and he has a past of throwing challenges just to prove a point. Aneesa knows how to make friends and be a competitor at the same time. But mostly, she knows how to command attention for all the right reasons, and it makes for some entertaining television

3. Darrell vs. 7. Tonya
Darrell had a great run on The Challenge and caught an easy first match-up, but Tonya is a shitstorm of crazy who subsists completely off of alcohol. A milquetoast Darrell has no chance against her. Darrell, watching you compete was great, but I’d rather see Tonya dump clothes into the pool every season than have you lying around the house. 

The Gulag

5. Coral vs. 8. Frank 
Coral has walked into every competition aware of herself, and she demanded that everyone notice. Even in The Gauntlet 3 when the veterans tried to screw her over, she demanded respect until they refused to give it... then she screwed them over instead. Frank, though, is like your one friend who gets blackout drunk every weekend and leaves you voicemails talking about the hot guy he just boned. It’s funny and entertaining at first, but it eventually gets really old.

2. CT vs. 6. Camila
Camila is insane in the best way, but she only has two gears: drunk or mildly competitive.  CT, on the other hand, gives us so many different sides of his personality. We’ve seen his sentimental side with Diem, his crazy side with every Challenger he’s ever had beef with, his playful side with his partners in recent Challenges as he tries to make them like him, and the best: the “I will destroy everyone in my way so that I can win” side. 

The Dome

1. Kenny vs. 4. Landon
This one’s a no-brainer. Landon plays by the rules. He doesn’t believe in alliances, and he plays a clean game. While that may be honorable, it’s far from the great television personality that Kenny has. Although Landon could easily beat Kenny in a physical competition, this bracket isn’t about physical capability; it’s about the capability and willingness to entertain viewers. 

2. Paula vs. 6. Katie
Katie may be a firecracker, but Paula has burned brighter for longer. Paula plays the game and has fun doing it, while Katie only has the underdog card to play. Paula is a stalwart competitor, but also understands how to get screen time and use it effectively. She’s fun, funny, and can shout around the house with the best of them. Katie is a good watch for a little bit, but she’ll always start to grate on the viewer eventually. 

Round 3

 

The Gauntlet

1. Bananas vs. 3. Laurel
It’s really easy to say that Bananas should take this one. He’s a Challenge legend, has the most wins, the most money made… he’s the overall number one seed! For the majority of his Challenge career, he’s been an easy target to hate; he uses everyone he can to win, and he’s screwed over friends to get to the finals. But there is something that almost comes off as inauthentic in him. Many of his jokes seem forced and sometimes they aren’t even funny. Laurel is very authentic. She says what’s on her mind, she doesn’t screw anyone over, and deep down she’s actually a sweet person (when she wants to be). She plays the game upfront and deserves respect for doing so. 

The Inferno

4. Aneesa vs. 7. Tonya
Aneesa was built for this show in a way that most other Challengers were not. She controls the house with her alpha personality and can vocally eviscerate anyone on command. Her physical performances are not always the best, but the girl lives for dominating eliminations. Aneesa is always stirring things up with talk about how awesome she is...everyone that gets in her way is just pathetic. In contrast, Tonya’s brand of crazy gets old after a while, especially when the cast turns on her. Aneesa’s bits always come across as entertaining.

The Gulag

2. CT vs 5. Coral
We all know Coral is a first ballot Challenge Hall of Famer. She was a legend even while she was still on the show getting everyone to do whatever she wanted with total impunity. Anyone that crossed her was going to feel her wrath, and that makes for a great Challenger. But then there’s CT. This is a dude that literally threatened to eat a guy’s face for crossing him. Nobody wants to mess with CT, and that includes the authors of this article.

The Dome

1. Kenny vs. 2. Paula 
Paula’s nutty behavior in the beginning of her Challenge career emphasized why we call her Paula Walnuts, but as her time on the show continued, her need to finally win turned her into a focused competitor. While she was still the Paula we love, she was a lot tamer. Kenny has never changed over the course of the show. He was an arrogant, pompous ass when he first started, and in his last appearance he was still hurting girls’ feelings, competing like a badass, and stirring up enough drama to make everyone hate and love him at the same time. Paula is arguably one of the most entertaining girls on the show, but Kenny (and Kenny Maria) move on to the Final Four.

Final Four

3. Laurel vs. 2. CT 
Laurel may have an extensive Challenge history of intense competition, but if The Challenge were an advertising firm, CT would be a Senior Executive and she’d be an intern. CT is so downright intimidating that Bunim/Murray brought him in to spice up the Cutthroat, leading to one of the most epic elimination rounds of all time. Meanwhile Laurel walks around like the HBIC she totally is, but people still try to eliminate her. No one touches CT. He’s gone from being a douchebag to a lovebird to a psychopath to a chill friend to a lovebird again, and now he’s resting on a combination of them all to consistently succeed in challenges. 

4. Aneesa vs. 1. Kenny
Aneesa had a really good run in this bracket. To start off against a beloved Challenge staple and make it all the way to the final four as one of the last two women standing is no small feat. While Aneesa can hold her ground with Kenny based on shit-talking and drama, there is something to be said for competing and winning, too. Aneesa may be an elimination round queen, but the best she’s ever done is third place. With Kenny, at least there’s a better chance for a win

The Challengionship

1. Kenny vs. 2. CT 
For most committed viewers, The Challenge has followed them over the years as they’ve grown up. Audiences have seen the show shift from the stupid, pointless, inane challenges (“who can keep their hands on this block of ice the longest?”) to crazy athletic, death-defying challenges (scaling the sides of skyscrapers, routinely climbing a mountain to win the final challenge). But let’s face it; The Challenge has always been a misogynistic show. The men treat the women terribly on a consistent basis. In the beginning, the men threw challenges to get rid of women so they could have stronger teams. Then, as the show changed and the producers found a way to work around the blatant disregard for the women’s physical abilities, men started openly berating women for any reason they could come up with. Kenny has always been one of those guys, even berating his female allies. In comparison, audiences have seen CT grow as a person. He started out as a pompous meathead, but over time he’s become one of the advocates for strong female competitors who get screwed over by politicking. CT has learned the error of his ways and has become one of the most respectful men in The Challenge house. 

But more than that, his history deserves to be recognized. The guy who acted like an ass when openly attacking team member Leah for being “weak” during Inferno became the guy that helped Cara Maria through an injured hand during Free Agents. The guy who verbally eviscerated Wes in The Duel became the guy that stood by Wes in Rivals 2. And the guy who was frequently disqualified for punching/nearly killing fellow challengers Davis and Adam became the guy more concerned with repairing his relationship with Adam than winning Rivals. Most viewers can probably admit to having hated CT at one point and then eventually loving him. It’s impossible to say that for Kenny. You either hate him or love him, with no in between. 

CT is still one of the most physically capable, most entertaining Challengers, and if you put him up against every other Challenger in this bracket (and Challenge history), he’d win every match.