Who has won the most seasons of MTV’s ‘The Challenge,’ explained

First known as Road Rules: All Stars and then Real World/Road Rules Challenge, MTV’s The Challenge has maintained a cult following since 1998. But in recent years, it’s branched out with spin-offs and onto other networks, and it’s developed into one of the most popular reality competition shows on television.

Unlike other series of its kind, The Challenge has always been fueled by recurring cast members who show up for several seasons. The most prestigious accolade a competitor can earn is Challenge champion — someone who has come out on top after a hard-fought season chock full of extreme stunts and grueling elimination rounds.

And after 38 seasons of the main show, no one has earned more championships than John Devenanzio — better known as “Johnny Bananas,” or just “Bananas.”

After making his reality TV debut on The Real World: Key West, Bananas joined the competition show for its 13th season, The Duel, in 2006. Fast forward 17 years and he’s taken part in 21 seasons and has won on seven separate iterations of the MTV staple. Further, Bananas also earned a trophy during one of the show’s many spin-offs.

So, let’s dive into Bananas’ career on The Challenge and how he became the most winningest star in the franchise’s history.

Bananas didn’t win his first show until 4 seasons into his ‘Challenge’ journey

Johnny Bananas didn’t come out of the gate as a major player during his first season of The Challenge. Actually, he was the first person eliminated from The Duel. It’s interesting to ponder: what if Bunim/Murray Productions and MTV never gave him a second chance after his quick departure?

Regardless, they decided to extend another invite and he returned for the show’s next iteration, season 14’s The Inferno 3, as part of the “Good Guys” team. Bananas had a much better showing that time around, making it to the final challenge while notching two Life Shields wins along the way. But, his team ultimately lost to their “Bad Asses” counterparts.

Bananas once again laced up his running shoes for his third season in a row, making him a Challenge veteran. But, his time on Gauntlet III went just like his experience on The Duel; he was the first male eliminated again. Going out first in two of three seasons was a rough start to Bananas’ legendary Challenge tenure, but he turned things around in a big way.

The Californian appeared on his fourth consecutive show, The Island, which was a season that largely reflected the CBS juggernaut Survivor. It was The Island where Bananas became a Challenge champion, splitting the $300,000 grand prize with Derrick Kosinski, Evelyn Smith, and Kenny Santucci.

After securing the treasure chest and his marooning on the secluded island ended, Bananas took a brief break from The Challenge. But, he returned for season 18’s The Ruins, which premiered in 2009, and he picked up his second straight title, winning alongside his fellow “Champions” teammates Evan Starkman and Susie Meister, as well as Derrick and Kenny. This season also featured one of Johnny’s most impressive elimination wins. He was thrown into The Ruins against the “Challengers'” final male competitor, the muscled-up Dunbar Merrill. Bananas defeated him in “Rag Doll,” a game that had the two wrestling for a piece of rope.

After ‘Fresh Meat II,’ Bananas competed in the next 15 of 16 seasons while winning five of them

After The Ruins, Bananas once again took a one-season hiatus from the reality competition series, skipping Fresh Meat II. He returned for season 20 which would kick-start a momentous Challenge run. Bananas appeared in every single season of the main show, from 2010’s Cutthroat through 2020’s Total Madness, besides season 23’s Battle of the Seasons.

All in all, Johnny triumphed over his competition five more times, bringing his total championship up to seven — two more than Chris “CT” Tamburello’s five (not including his two “Champs vs.” wins). Speaking of CT, Bananas’ 15-season run started with one of the most iconic moments in Challenge history; but, it was at Bananas’ expense.

CT showed up as a mercenary during Cutthroat and he and Johnny Bananas battled it out in “Back Up Off Me,” an elimination round that had the two competitors strapped together back to back. CT only needed a few seconds to lift Bananas off the ground to carry him like a backpack, leading to the latter’s exit from the show.

Bananas would earn vengeance over CT in the next season, however. They both showed up on Rivals and Bananas earned his third title by winning the 21st season with his partner, Tyler Duckworth. And along the way, the two took CT and partner Adam King out of the game in a physical, head-to-head elimination round.

Battle of the Exes marked Johnny’s next championship, which came right after Rivals. He won the season alongside Camila Nakagawa.

Next, Battle of the Seasons played out, but Bananas was off relaxing and marinating in his second consecutive victory. However, that would be his last break for eight years.

He and teammate Frank Sweeney placed second behind CT and Wes Bergmann in season 24’s Rivals II. Undeterred, Bananas came back and made history in season 25’s Free Agents by setting the championship record. In what was the franchise’s first individual-based game since season 17’s The Duel II, Johnny Bananas beat out the male field and scored his fifth crown, surpassing Darrell Taylor’s record of four.

Although Bananas was used to either winning or at least making it onto the podium, he’d be eliminated before the final challenge in his next two shows: season 26’s Battle of the Exes II and season 27’s Battle of the Bloodlines.

Then, Rivals III went Bananas way — big time. He and Sarah Rice (now Sarah Patterson) dominated season 28 and worked as a well-oiled machine up until they passed the finish line in first place. But, a twist soured their pairing and created arguably the most savage moment in the show’s nearly 40-season run. Because he earned the most points during the final challenge, Bananas had the option to split the $275,000 grand prize with Sarah or keep it all for himself. He elected the former, leaving her penniless.

Interestingly, that move would be the starting point of his career’s worst losing streak. He wouldn’t see a final challenge — let alone hoist gold — for his next six seasons. Many, including Johnny, would joke that he was cursed because of his brutal decision. He was booted before finale night on season 29’s Invasion of the Champions, season 30’s Dirty 30, season 31’s Vendettas, season 32’s Final Reckoning, season 33’s War of the Worlds, and season 34’s War of the Worlds 2.

It wasn’t until Johnny’s 20th season that he extended his championship record to seven. Bananas won his second show as an individual, besting Kyle Christie, Cory Wharton, Faysal “Fessy” Shafaat, and Rogan O’Connor in the final challenge of season 35’s Total Madness. After finally breaking the curse, Johnny announced that he’d be walking away from the show, but was vague about when — or whether — he’d return.

Bananas has competed twice since ending his hiatus

Bananas would end up sitting on the shelf for around two years, missing out on season 36’s Double Agents and season 37’s Spies, Lies & Allies. The Challenge legend couldn’t stay on the sidelines, however. He made his grand return on season 38’s Ride or Dies where he’d make it to the final challenge and place second alongside Nany Gonzalez, and losing out to Devin Walker and Tori Deal.

Ride or Dies is the last season to air under MTV’s main series, which wrapped in March. But, he popped up on Paramount+’s World Championship, the most recent season of The Challenge which ran from March until May. Bananas and partner Justine Ndiba, an alum from CBS’s The Challenge: USA, made it halfway through the season before dropping an elimination round to the season’s eventual winners, Jordan Wiseley and Kaz Crossley.

Bananas also won 2017’s ‘Champs vs. Stars’

When calculating the number of championship wins, the Challenge community typically doesn’t count some of the spin-off shows, specifically the “Champs vs.” iterations, because of the shows’ quick filming time and less-intense nature. There were three in total that premiered between 2017 and 2018: Champs vs. Pros, Champs vs. Stars (2017), and Champs vs. Stars (2018).

Bananas competed in the first two spin-offs. He was the first male kicked off from the “Champs” team during Champs vs. Pros after losing the grudge match between him and Wes. But, Bananas got back to his winning ways during 2017’s Champs vs. Stars. During the final challenge, the “Champs” squad featuring him, CT, and Emily Schromm, beat out the “Stars” crew that was represented by UFC women’s strawweight fighter Michelle Waterson, rapper Justina Valentine, and The Bachelorette alum Josh Murray.

Compared to the “Champs vs.” trilogy, All Stars and the World Championship series are more likely to be considered by Challenge fans (including this writer) as actual wins. But, Bananas has yet to appear on All Stars through three seasons.

Lastly, even though Bananas is the all-time record holder for most championship triumphs, he hasn’t won the most grand prize money. That honor goes to CT, who has nabbed $1,365,000 compared to Bananas’ $1,184,720, per Looper.