Over the years, The ChallengeIt has become a popular sport. That’s definitely the case if you ask some of those who have won multiple times — and there are quite a few.
“We’re literally dangling from tanks, explosions are feet away from us. I mean, the amount of danger and just insanity that takes place with the challenges,” six-time champ Johnny “Bananas” DevenanzioTells Use. “They really ratcheted up the insanity and the danger level in season 35. It’s not just our living conditions, but the challenges. What are you guys gonna think of next?”
Since its debut in 1998, the show has continuously changed — from formats to hosts, to competitors. However, there are some stars who just can’t stop winning. Johnny, for instance, joined the series in 2006. The Duel. He has competed on 20 seasons and still holds the title for the most wins, his latest being 2021’s Total Madness.
Mike “The Miz” Mizanin, one of the most successful to come out of the show, still returns to host reunions — and is still thankful.
“I love that show. MTV is where I got my start. And so I will always come back to MTV and always do whatever they need me to do, because that’s what they gave me,” the Real World alum says. “They gave me my start. They gave me the confidence to become a WWE Superstar and led me to where today. It’s a show I love. Every time it’s on, it’s everyone’s guilty pleasure.”
The format of the show was almost always teams, but sometimes it was a combination of both. ChallengeYou could have as many as nine winners. Over the years, the game evolved and the winning teams became smaller.
Who has won more than one? ChallengeWhat was their time like? There have been many multi-time winners, some still competing today. Look through the gallery to see where they are at the moment.