Ranking 21 of the Most Memorable Contestants From MTV’s The Challenge

21. Kyle Christie & Paulie Calafiore

  •  # of Challenges- Kyle (3), Paulie (2)
  • Finals- Kyle (Vendettas), Paulie (Final Reckoning)
  • Money Won- Kyle ($20,625), Paulie ($0)

Kyle and Paulie’s inclusion on this list is equal parts respect for their current status, and a nod to their future. There are plenty of other contestants that are deserving, but these two are currently making a huge impact. Both men gained famed through other shows — Kyle via Geordie Shore, and Paulie via Big Brother. Kyle made his debut on Vendettas and impressed immediately. He formed a relationship with Challenge legend Cara Maria, and won three daily challenge’s en route to a third place finish.

Paulie arrived on the scene last season, and claimed third place alongside Natalie — another a Big Brother alum — on Final Reckoning. Paulie created national headlines following his hookup with Kyle’s ex, Cara Maria, due in part  to having a relationship at home with former Bachelor contestant Danielle Maltby.

The two men are currently marred in a heated rivalry on War of the Worlds. Both Kyle and Paulie are fierce competitors. Kyle is an imposing figure, while Paulie is a superior athlete capable of winning nearly every daily challenge. In addition to being physical threats, the two have explosive personalities that make for great television. There is no reason to believe these two will not be a crucial part of the series going forward.

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20. Diem Brown

  • # of Challenges- 8
  •  Finals- The Gauntlet III, Battle of the Exes
  •  Money Won- $53,000

One of the most beloved people to ever grace MTV’s airwaves, Diem Brown tragically lost her battle with ovarian cancer in 2014. Diem’s personality and wit led to her quickly becoming a fan-favorite. Despite never winning a season, Diem routinely advanced far in the game. After coming up just short on The Gauntlet III, Diem earned second place on Battle of the Exes. Diem was paired with CT — her former longtime boyfriend. Diem twice fought cancer and returned to compete, but tragically had to step away from her final Challenge, Battle of the Exes II, when her cancer returned a third time. Diem’s legacy has lived on through her family, fellow Challenge contestants, CT, and MTV.

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19. Ashley Mitchell

  • # of Challenges- 5
  •  Finals- Invasion of the Champions (won), Final Reckoning (won)
  •  Money Won- $1,121,250

Ashley hasn’t been a fixture for as long as many of her fellow Challenge legends, but she has certainly made a lasting impact on the franchise. After making a respectable run in her first showing on Rivals III, Ashley thrust herself into the limelight through her work on Invasion of the Champions. Ashley isn’t afraid of the big moments, as evidenced by her two challenge victories during Invasion en route to an impressive victory in the final challenge. However, what really separates Ashley is her stunning actions at the end of Final Reckoning. Coupled with former love interest turned rival, Hunter, the duo was nearly unstoppable leading up to the finale.

Pitted against three other teams, the winning team would claim the $1,000,000 prize — with one caveat. The individual partner whom finished with a better time would decide whether the prize would be split, or kept to him or herself. Ashley and Hunter outlasted the others, with Ashley besting Hunter in the end. When it came time to make a decision, Ashley buried Hunter verbally and decided to keep the money for herself. In making that decision, Ashley has become one of the biggest villains in Challenge history. Hunter, however, got a piece of revenge just two episodes into the follow-up season — War of the Worlds — and eliminated Ashley from the competition.

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18. Mike “The Miz” Mizanin

  • # of Challenges- 5
  •  Finals- Battle of the Seasons ’02 (won), The Gauntlet, The Inferno, The Inferno 2 (won)
  •  Money Won- $130,500

The most well-known individual to come from The Challenge universe is undoubtedly, The Miz. Before he became a WWE Superstar, Miz was known as the brash loudmouth from The Real World: Back to New York. Miz went around the house displaying his dream wrestling character, which would eventually become a reality five years later. In between his Real World season and WWE star-turn, Miz was a force on The Challenge. Miz displayed his knack for the game immediately, winning Battle of the Seasons (2002) in his debut Challenge. He fell short of winning in the two subsequent finals, but Miz once again claimed glory in The Inferno II — his final seasonThe Miz has become a global star courtesy of his time with the WWE. He has 18 total championships under his belt, and remains a main event character. He has also recently made an impact on the Challenge scene, acting as the host for multiple reunions and specials.

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17. Sarah Rice

  • # of Challenges- 9
  •  Finals- The Ruins, Cutthroat (2nd), Battle of the Seasons ’12 (3rd), Battle of the Exes II (won), Rivals III (won)
  •  Money Won- $173,689

Poor, poor Sarah. Despite being one of the best female competitors in Challenge history, she will always be remembered for anything but her own ability. Before diving into one of the most memorable moments in reality television history, let’s look at Sarah’s impressive Challenge résumé. Out of the nine competitions she has been a part of, Sarah has reached five finals. At the conclusion of her past two shows, Sarah has come out on top. Sarah partnered with Jordan Wiseley to win Battle of the Exes II, and claimed the throne on Rivals III alongside Johnny Bananas. While Sarah technically won Rivals III, she ended up being the biggest loser of the season. In what has become The Challenge’s most memorable moment, Bananas elected to keep all of the money to himself — leaving Sarah with nothing. After all of her hard work, she received $0 of the $275,000 prize. Sarah hasn’t returned to the show since being betrayed by Bananas, and there is nothing to suggest she will ever be back.

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16. Jordan Wiseley

  • # of Challenges- 4
  •  Finals- Rivals II (3rd), Battle of the Exes II (won), XXX: Dirty 30 (won)
  •  Money Won- $583,000

Perhaps the most impressive contestant in Challenge history due to his physical limitations, Jordan has proved to be one of the most dangerous players throughout the show’s many seasons. Born with only one fully functional hand, Jordan has made the most of his chances. Despite not being a great political player, Jordan has consistently made it far on the show. Partnered with the supremely-athletic Marlon on Rivals II, the duo survived two eliminations before ultimately finishing in third place. After a disappointing performance on Free Agents, Jordan has won two consecutive seasons — Battle of the Exes II and Dirty 30. Jordan is also 5-1 in eliminations and has 11 daily challenge wins to his name.

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15. Abram Boise

  • # of Challenges- 9
  •  Finals- The Inferno (won), The Inferno II, The Inferno III (won), Cutthroat (2nd)
  •  Money Won- $103,500

Abe is a very good competitor. He has shown to be an intelligent guy and is clearly a physical threat. However, Abe is also a hothead — to say the least. He has been kicked-off multiple seasons of Road Rules due to physical altercations with fellow contestants. Abe was a feared, yet respected, player during his time with The Challenge. When he was locked in on the competition, there weren’t many people who could keep pace with Abe. He was a dominant player during the Inferno trilogy, and remained a top-contender throughout his tenure. He doesn’t have a standout record in eliminations, due in part to other players seeking to avoid head-to-head matchup’s with the fiery figure. Abe is also famous for his dramatic relationship with Cara Maria, who would become the main catalyst in a few heated moments involving Abe. It would be a surprise to see Abe return to the show, but it sure would be entertaining.

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14. Mark Long

  • # of Challenges- 6
  •  Finals- Real World/Road Rules Challenge (won), Battle of the Sexes (won), The Gauntlet 2, The Duel II (3rd)
  •  Money Won- $80,184

Mark Long is one of the true OG’s of The Challenge. Mark was a member of the first Challenge in history, Real World/Road Rules Challenge. Mark was a member of a stacked Road Rules squad, which only lost one daily challenge. After securing a title, Mark went on to also win Battle of the Sexes. After a fourth place finish on Battle of the Sexes 2, Mark reached two more finals. Mark is one of the best all-around players in Challenge history. In addition to being a competition beast, Mark was universally liked by his peers. Rumor has it that Mark has been pining for a return at the age of 47…does he still have it in him?

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13. Camila Nakagawa

  • # of Challenges- 10
  •  Finals- Battle of the Exes (won), Rivals II (3rd), Invasion of the Champions (2nd), XXX: Dirty 30 (won)
  •  Money Won- $561,250

The lingering question hovering over Camila is, will she ever return to The Challenge? Easily one of the best female competitors in reality history, Camila has not been asked back to the show following a string of despicable behavior. The discussion of whether she should be allowed to return is for another day. The truth is, had it not been for her bad choices, Camila may have been seen as the female face of the franchise. After a slow start to her career, the Brazilian won Battle of the Exes. Camila and Jemmye won two elimination rounds en route to a third place finish on Rivals II. One of Camila’s greatest achievements was knocking out Laurel on Invasion of the Champions. In her last main Challenge, Camila was victorious on Dirty 30. Two victories, a 9-4 record in eliminations, and over $500,000 in career-winnings — Camila is a devil of a competitor.

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12. Evelyn Smith

  • # of Challenges- 7
  •  Finals- The Inferno 3 (won), The Gauntlet III, The Island (won), Rivals (won)
  •  Money Won- $167,000

Evelyn may be one of the most underrated contestants in Challenge history due to her lack of appearances. Physically gifted enough to turn down a softball scholarship, Evelyn made the competition side of the game look easy. After an early exit on Fresh Meat at the hands of Wes, Evelyn reached three-straight finals. She rolled through The Inferno 3, narrowly lost The Gauntlet III, and stormed through The Island to win her second season. In her last appearance, Evelyn teamed up with Paula on Rivals, and promptly won her third season. It was evident Evelyn possessed a mind that equaled her physical ability. Having not appeared on The Challenge since Rivals, Evelyn focused on school. After attending the University of San Diego, the star graduated from Harvard Law School in 2016.

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11. Emily Schromm

  • # of Challenges- 3
  •  Finals- Cutthroat (3rd), Battle of the Exes (3rd), Rivals II (won)
  •  Money Won- $55,000

If Emily Schromm wanted to make a career out of The Challenge, there is no doubt she would be the greatest female competitor of all-time. As it stands, Emily has only appeared on three main seasons — and one Champs vs. Stars season, which she won — and has reached the final all three times. Over the course of those three seasons, Emily sports a perfect 5-0 record in eliminations. She partnered with Paula and coasted her way to a Rivals II victory. Off the screen, Emily is a huge personality in the fitness world. At one time named Women’s Health’s Next Fitness Star, Emily has found a perfect way to showcase her athletic ability. If she decides to compete once again, the rest of the house will surely need to step up their game.

Image Source: Denver Post Photo by Cyrus McCrimmon

10. Evan Starkman

  • # of Challenges- 6
  •  Finals- The Gauntlet III, The Duel II (won), The Ruins (won)
  •  Money Won- $151,293

If it weren’t for his forced departure, would Evan be mentioned among the best of the best? Probably. Is it fair to say, regardless of his departure, that he is among the best? Yes. Evan was one of the best players in the game almost immediately upon his arrival. On his first season, Fresh Meat, Evan and his partner, Coral, won five of the first six daily challenges. On The Duel, he won six more daily’s before being eliminated by CT. He won 10 more on The Gauntlet III. It wasn’t until The Duel II that Evan won his first final, but he didn’t wait long to add to the trophy case — as he also took home first on The Ruins.

On Evan’s last Challenge, Rivals, he was once again eliminated by CT. For as good as he was physically, Evan’s greatest attribute was his political game. In teaming up with Bananas and Kenny, Evan always had an advantage entering the game. It is a shame we will never see him compete again, but his game play will remain highly valued.

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9. Kenny Santucci

  • # of Challenges- 8
  •  Finals- Fresh Meat (2nd), The Inferno 3 (won), The Gauntlet III, The Island (won), The Ruins (won), Fresh Meat II (2nd), Rivals (2nd)
  •  Money Won- $236,293

Kenny can’t hold a candle to many of the show’s greats when it comes to daily’s and eliminations, but he may be the torch bearer when it comes to the political game. Kenny appeared in 7-of-8 finals, and only faced elimination six times. He totaled 35 daily wins and a 5-1 record in eliminations. Kenny had the ability to talk anybody into a game move that he wanted — even if it meant convincing a rival to do something in his favor. Kenny often allowed Bananas and, to a lesser extent, Evan take the heat for moves the group made. Fresh Meat II was far and away his best season, as he and Laurel dominated throughout the competition. His two biggest blemishes remain his performance in Rivals, and his ouster from the franchise. Despite coming in second on Rivals, Kenny was clearly the weaker partner compared to Wes. Like Evan, Kenny is in essence blacklisted from the show and will likely never return.

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8. Landon Lueck

  • # of Challenges- 4
  •  Finals- The Inferno II (won), The Gauntlet 2 (won), Fresh Meat II (won)
  •  Money Won- $184,166

The only thing holding Landon back from topping this list is his lack of experience. A veteran of only four seasons, Landon is arguably the most dominant player the game has ever seen. He won his debut Challenge, The Inferno II, and doubled-down by winning his next Challenge, The Gauntlet II. Landon was well on his way to another victory on The Duel II, until Brad pulled a rabbit out of his hat to hand Landon his only defeat. Landon returned for one final season, Fresh Meat II, and won his third Challenge in four tries. Landon didn’t have much of a political game to speak of, mainly because it didn’t seem to be important to him. With his athletic prowess, it didn’t matter at all. If he returns to The Challenge, however, he may need to immerse himself more into the fabric of the game.

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7. Laurel Stucky

  • # of Challenges- 5
  •  Finals- Fresh Meat II (2nd), Cutthroat (2nd), Rivals (2nd), Free Agents (won)
  •  Money Won- $201,000

If there is any female competitor that can stand up to Emily’s physicality, it’s Laurel. To say Laurel is a competition beast would be an understatement. Despite competing in only five Challenge’s to date, Laurel has stacked up 17 daily victories. If anyone doubted her ability to win as an individual, Laurel made sure there was no mistaking her dominance with her performance on Free Agents. En route to winning her first Challenge, Laurel won four eliminations — knocking out the likes of Aneesa and Cara Maria. Her first and only elimination defeat came at the hands of Camila on Invasion of the Champions. With a 9-1 record in eliminations, and no worse than a second place finish on any season, Laurel is clearly the most feared female competitor in Challenge history. If she comes back, there is no clear candidate to take her out.

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6. Derrick Kosinski

  • # of Challenges- 10
  •  Finals- The Inferno II, The Inferno 3 (won), The Island (won), The Ruins (won), XXX: Dirty 30 (2nd)
  •  Money Won- $211,293

Derrick may not get the credit he deserves. By competing alongside the likes of Bananas, CT, Wes, Kenny, and Evan, Derrick is sometimes put on the back burner. However, when you account for his size, Derrick is arguably the most tenacious Challenger pound-for-pound. After reaching the final of The Inferno II, Derrick showed up to The Gauntlet 2 on a mission. Derrick was sent into Gauntlet after Gauntlet, and came out on top four-straight times. Derrick was ultimately eliminated right before the final, but he would avenge his loss tenfold.

Two more seasons of heartbreak separated Derrick from his goal. Then, starting with The Inferno 3, Derrick won three-straight Challenge’s. Add in a second place finish on Dirty 30, and Derrick is arguably on one of the best streaks the series has seen. An absolute pit bull in eliminations, Derrick holds a sterling 8-4 record. Currently sitting out War of the Worlds, Derrick is busy hosting the Challenge Mania podcast.

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5. Cara Maria Sorbello

  • # of Challenges- 13
  •  Finals- Cutthroat (2nd), Rivals (2nd), Rivals II (2nd), Battle of the Bloodlines (won), XXX: Dirty 30 (2nd), Vendettas (won), Final Reckoning (4th)
  •  Money Won- $602,250

The female face of the franchise, the Challenge queen, Cara Maria. Since her debut on Fresh Meat II, Cara has been a polarizing figure. Seen as a quirky loner who had a thing for the resident bad boys, Cara’s game wasn’t immediately respected. Despite finishing second on Cutthroat, Rivals, and Rivals II, Cara didn’t breakthrough until Battle of the Bloodlines. However, where Cara really gained momentum was the season Dirty 30. Cara returned from the Redemption House and ended up finishing second for a fourth time.

On Vendettas, Cara became the first sole winner in Challenge history when she narrowly edged out Zach for nearly $400,000. Despite finishing fourth on Final Reckoning, Cara’s game that season — and currently on War of the Worlds — has been overshadowed by her drama with Kyle and Paulie. If people can look past her public spats, it is clear Cara is a true Challenge legend. A constant threat to take home the grand prize, Cara is tough to eliminate. In 19 eliminations, Cara holds an impressive 13-6 mark.

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4. Wes Bergmann

  • # of Challenges- 11
  •  Finals- Fresh Meat (3rd), The Duel (won), Rivals (2nd), Rivals II (won)
  •  Money Won- $248,000

Wes is as polarizing as they come. If you are a staunch Bananas’ defender, you likely despise Wes. If you can’t stand Bananas, Wes is probably your guy. Both a top-notch competitor and one of the shrewdest players in Challenge history, Wes probably doesn’t have the results his overall game should have yielded to this point. Despite being stuck with Casey — one of the worst competitors the show has ever seen — on Fresh Meat, Wes was responsible for five elimination victories and carried the duo to third place. In one of Wes’ best moments, he defeated in Derrick in what is regarded as one of the best eliminations in series’ history — and went on to win The Duel.

After being bogged down by having to deal with the super trio of Bananas, Kenny, and Evan for two seasons, Wes reached the Rivals final while partnered with a sub-par version of Kenny. Wes once again reached the mountain top on Rivals II, as he teamed with CT to take the throne. Brash, confident, and antagonistic, Wes has taken part in more eliminations than any other Challenger. He also has the most victories with 19 overall, leaving the star with a 19-6 record. Wes recently returned for War of the Worlds, after last appearing on Rivals III.

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3. Darrell Taylor

  • # of Challenges- 8
  •  Finals- The Gauntlet (won), The Inferno (won), The Inferno II (won), Fresh Meat (won)
  •  Money Won- $243,055

Darrell is a guy nobody wants to mess with, just ask Brad. Darrell has been in and out of the mix since his debut on The Gauntlet. He started off his career with a bang, winning the first four Challenge’s he was a part of. Remarkably, Darrell only appeared in one elimination over the course of those four seasons. Now, back to Brad. Going for his fifth-straight Challenge win, Darrell appeared to be full-steam ahead on The Ruins. He defeated both Danny and Cohutta in eliminations, and showed no signs of relinquishing his crown. Then, Brad instigated Darrell into attacking him. Both men were immediately disqualified, thus ending Darrell’s quest for a five-peat.

The following season, Fresh Meat II, saw Darrell shockingly lose Episode 1. Following a seven-year hiatus, Darrell returned for Invasion of the Champions. He reminded his fellow competitors why he is a four-time champion by eliminating Zach and Bananas. Ultimately, CT ended Darrell’s run right before the final. Approaching 40, Darrell may not have many Challenge’s left in him — though he remains a true legend of the game.

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2. Chris “CT” Tamburello

  • # of Challenges- 15
  •  Finals- The Inferno, The Inferno II, The Gauntlet III, Battle of the Exes (2nd), Rivals II (won), Invasion of the Champions (won), XXX: Dirty 30 (3rd)
  •  Money Won- $265,000

Let’s face it — an in-shape and determined CT is the most unstoppable force in Challenge history. He may not have the most wins under his belt, but there is no denying his greatness. Despite having to leave three shows early — Inferno III and Duel II for fighting, Exes II for Diem — the titan has reached seven finals, and had advanced to at least the final elimination 10-straight times up until Final Reckoning (with the exception of his DQ’s). Between the main seasons and Champs vs. Stars, CT has 56 daily victories and nine elimination wins. In addition to his two main Challenge titles, he has also won Champs vs. Stars two times in a row. No longer the hothead he was early on, CT has become one of the most well-respected players in the game. When he’s engaged, there aren’t many players capable of standing up to CT’s power or wit.

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1. Johnny “Bananas” Devenanzio

  • # of Challenges- 18
  •  Finals- The Inferno 3, The Island (won), The Ruins (won), Rivals (won), Battle of the Exes (won), Rivals II (2nd), Free Agents (won), Rivals III (won)
  •  Money Won- $685,543

Out of all the many legends that have spawned from The Challenge franchise, there is one man that stands above them all. He isn’t the most physically gifted. He certainly isn’t the best in head-to-head eliminations, but Johnny Bananas is The Challenge. Between the main shows and the spin-off, Bananas has appeared on 20 seasons since his debut on The Duel. He has 62 daily victories, six Challenge wins, and one Champs vs. Stars title. Bananas has made a career out of being the most outlandish character on the show. He is a master manipulator and the greatest political player the show has ever seen. From The Inferno 3-Rivals III, Bananas went on an absolute tear. He reached 8-of-12 finals, taking home six Challenge titles and cementing himself as the most iconic Challenge participant of all-time.

The most infamous moment in the show’s history took place at the end of Rivals III. As discussed earlier, Bananas opted to keep the entire grand prize instead of splitting it with his partner, Sarah. In what has become one of the most watched moments in reality television history, Bananas made his decision with no hesitation. Although he hasn’t finished higher than fifth since his historic move, Bananas will remain The Challenge’s foremost participant until he decides to move on.

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