The Challengehas been a critical component ofMTV’s success. The reality competition show that started as a spinoff fromThe Real Worldfranchisecame to become its entity and has brought names into the industry that will be recognized for many years. With its 40th season coming up soon, it’s time to identify why the show is as great as it is; many personalities from this show have left their mark and made reality television history. Names likeJohnny Bananas, Jordan Wiseley,CT Tamburello,andCara Maria Sorbellohave made their mark on the franchise and have named themselves some of the best players of the show with multiple seasons under their belt and showcasing what it takes to have a good game plan.
With the show introducing many new players that will eventually take over thelegacy of older players, the new people need to take notes from the veterans and their past seasons to ensure they have the same impact. From exes to rivals to stealing the money and being the sole winner, many seasons have become cultural phenomena that can make it challenging to choose the best, but these seasons have created the most impact.

The Challenge
15’Battle of the Seasons'
The 2002 series wastruly the game-changer forThe Challenge.Teams of two comprised ofThe Real WorldandRoad Rulescast members represented their seasons as the two franchises did battle to see who would prevail in the end. This season was a complete switch from the previous season where there were two teams from each series competing against one another. The season sawMark LongfromRoad Rules: The First AdventureandEric NiesfromThe Real World: New Yorkserving as hosts.
There were some majorly iconic moments throughout the season, includingBelou Dex Texbringing her baby to the game and the hurricane that almost destroyed the entire season. In the end, TeamReal Worldwon out, but they did make a deal withmostof theRoad Rulesplayers to ensure everyone was walking away with a monetary prize at the end. The biggest casting decision from this season was the pairing ofThe Real World: Back to New York’sMike “The Miz” MizaninandCoral Smith. Their dynamic made these ride-or-dies became instant legends of the series.

14’Fresh Meat'
WithRoad Rulesslowly coming to an end, the series needed to find new blood to join the roster of future Challenges. The series watches as12 newbies were paired with legendary alumfromRoad RulesandThe Real World. Week by week, pairs would be eliminated until three teams remained. The winners wereDarrell Taylorand his fresh meat partnerAviv Melmed, who has now broken her absence with an appearance onThe Challenge 40: Battle of the Eras.
This season trulyset the course of the second era of the series. First, it was the first time alumni fromThe Real World: Austinappeared on the show. This wasWes Bergmann’s first time reaching the final and solidifying himself as a competitor. From theFresh Meatside, it introduced the world toKenny Santucci, Evan Starkman, Evelyn Smith, andDiem Brown.

13’Battle of the Seasons’
Former stars fromThe Real WorldandThe Challengeunited to determine which cast was the best of the best. For this season,teams of four former roommates competed in hopes of being the Power Teamin order to place one team into The Arena. That team would then choose one male and one female member of their team up for elimination. They would face off against the losing team of the week. The 8 teams of 4 included 7 teams fromThe Real Worldand one composite team comprised solely ofFresh Meatcast members.
Like many series before it, the series allowed many new faces to start to take their place inThe ChallengePantheon, establishing themselves as key figures in the show’s history. In the end, the entire quartet fromThe Real World: San Diegowon the prize. The season saw the reunion ofThe Real World: AustinexesDanny JamiesonandMelinda Stolpand the return ofTrishelle CannatellafromThe Real World: Las Vegas.

12’The Inferno'
The Real Worldwas pitted againstRoad Rulesin a season that took on a similar format toThe Gauntlet. As one of the seasons that helped launch storylines that would linger for seasons to come, the first iteration ofThe Infernobrought immense drama and major legends of the game. This season proved that likely due to the format of their original program, the players from Road Rules would always dominate, causing the sequel editions to change the team format to Good Guys versus Bad Asses.
TeamRoad Rulestried everything they could in hopes of having the best team they could at the end, so they usedKatie Cooleyas a scapegoat. They would toss challenges to send her into the elimination. Meanwhile, Team Real World were thrilled to have her as their unofficial mascot. It did work out in the end for Katie as she did win alongside the individuals who tried to eliminate her. But, by far,the most memorable moment of the season involved Julie Stoffer taking off Veronica Portillo’s safety harness.

11’Fresh Meat II'
Like the first iteration ofFresh Meat, the second edition was another game changer for the franchise. Set in Whistler, British Columbia, this was the first time the show officially was changed toThe Challenge. With the new generation of players establishing new battle lines, immense rivalries, includingKenny SantucciandWes Bergmann, became a central storyline for the season. In the end, nice guys can finish first, asLandon Lueckand his partnerCarley Johnsonwere victorious.
In a shocking turn of events,Darrell Taylor, the winner of the firstFresh Meat, found himself eliminated first. What was more shocking was that his partner,Cara Maria Sorbello, would be invited back for future seasons after her first run. Second chances truly do work out in your favor! The season helped launch the careers of Cara Maria,Laurel Stucky, Theresa Gonzalez, andBrandon Nelson.
10’Rivals I'
Something thatThe Challengeis very well known for is creating rivals throughout the franchise. Many of the players at this point have known each other for years. Whether they met throughThe Challengeor during their time onThe Real World,this show thrives on drama, which is why it was essential to createRivals.This season was chaotic because of the influential personalities in it. The premise of this season was to have pairs of people who have blatantly told each other that they hate them and have them compete for a grand prize.
Some of the pairings were CT Tamburello andAdam Kingsince they had an altercation during their season ofThe Real World: Paris,Wes Bergmann,andKenny Santuccibecause, throughout their time on the show, they have always said how much they disliked each other, and Cara Maria Sorbello andLaurel Stuckybecause they were not the best of friends during their breakout season ofFresh Meat II.By having pairings in which they hated each other, it would be challenging for the players to put their trust in each other when they wanted to rip each other apart. Ultimately, the winners were Johnny Bananas andTyler Duckworthfor the men andEvelyn SmithandPaula Meronek for the women.This show brought the drama, the altercations, and a heated finale in which no one knew who to root for because every player was in their prime.
9’Cutthroat'
Cutthroathas one of the most memorable moments in Challenge history regarding iconic moments of reality television that will go down in history. This season brought many fan-favorite challengers into one, and it became the first season in which there would be multiple winners since it was a team competition. What could go wrong if prominent personalities compete against each other for money and work in teams? The separation of the teams would be a critical factor in how the season would be handled, and the division would be perfect. Having Johnny Bananas andDerrick Kosinskiin the blue team, they were the straight leaders of that team,Brad FiorenziandTori Fiorenzicontrolled the red team, andAbram Boiseand Cara Maria were the leaders of the grey team.
The gameplay of this season was fascinating because it was a veteran-run game. It would be easy to throw in a rookie if anyone went into an elimination. Still, once the competition started getting more demanding and challenging, they had to throw in vets for elimination, creating the best moment ever. Johnny Bananas was unfortunately thrown into elimination, but he may have thought he had it easy with his opponent until he saw he was going against a mercenary to move on to the final. It was C.T. After being on pause for physical altercations with Adam King, this was his big comeback, and he made an impression. They were strapped into each other during the elimination and had to drag the opposing player to a barrel to win. It seemed easy for a man’s elimination, andBananas seemed formidable enough, but he did not expect C.T. tocarry him like a backpacktwice and lose right before the final.
8’Rivals III'
At this point, Johnny Bananas had made his mark onThe Challengeand created many rivals throughout his time on the show. DuringRivals III,it was the same asRivals I,in which teams would be with their rival, but this time around, it was male and female rivals, which brought even more drama into it. This was an iconic season because it was one of the first timesthe show brought in people from anotherMTVshow,Are You the One?,which created the rivalry betweenDevin WalkerandJohnny Bananas. Of all the Bananas wins he has, this one was important and crazy because he was with his rivalSarah Patterson.
At the beginning of the season, they thoroughly despised each other because of Sarah’s decision in the past season, and Bananas could not get over it. Still, as the season progressed, they became a powerhouse and the clear winners, but they were not expecting the twist of all twists. When they won,TJ Lavin allowed Johnnyto choose whether to share the money with Sarah (he beat her at making the final in less time) or take the money and run. Many people thought he would share, but he made the crazy move of taking the money away from Sarah, which declared him the biggest villain in reality T.V.
7’Free Agents'
WithFree Agents,the show was taking a chance of having all the players go against each other and only having one winner. It was a fun season to see how everyone would use their skills and politics to get out of eliminations and make it to a final. The season also had an exciting elimination format by havingcontenders flip different boards until someone got the “kill” card and go into an elimination immediately.Having to decide their fate by chance only made the players more nervous, and having to scramble around who should go down to determine their fate.
During this time, it was Jordan Wiseley’s second season, and after showing his skills inRivals II,it would be interesting to see how he could handle his own game. He was coming in as a strong rookie and full force against Johnny Bananas, which led to one of the most excellent eliminations in which Bananas was waiting for his opponent, and Jordan decided to make the move of flipping all the tables and send himself to elimination to go against one of the GOATS of the show finally. Ultimately, he was all talk and was humbled quickly after Bananas went on to eliminate him and win the season.
6’Battle of the Exes'
BesidesThe Challengeconstantly creating enemies, it has also had some luck at creating relationships that have flourished after the show or creating the downfall of terrible relationships. EnterThe Challenge: Battle of the Exes,in which exes from throughout the franchise come together and work as a team to win the competition. This season had many iconic and sometimes questionable couples, but the drama it brought was intriguing for viewers because, in some partnerships, it was a will they not situation.
The most iconicChallengecouple has always been C.T. andDiem Brown.The pair met each other during the show, and their chemistry was undeniable. After many ups and downs during their relationship,seeing them as viewers work together and make it to the final was a beautiful moment for the franchise and brought closure to the two of them. C.T. and Diem were the fan favorites to win the whole season, but had it not been for Johnny Bananas andCamila Nakagawa,they would have been able to win. This season has a great cast, but the final is a full-circle moment for viewers to see how well C.T. and Diem worked.