Over the years, The Challenge has become a 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” Devenanzio tells Us. “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 example, joined the series in 2006 on 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. And I always feel like like, MTV gave me 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 that I needed to become a WWE superstar and to lead me to where I am today. So I love the show. Every time it’s on, it’s everyone’s guilty pleasure.”
In the beginning of the show, the format was almost always teams and sometimes a Challenge could have up to nine winners. Over the years, the game changed and winning teams became smaller and smaller.
So, who has won more than one Challenge during their time? There have been quite a few multi-time winners, some of who are still competing today. Scroll through the gallery below to see where they are now.
Seasons won: All Stars and Battle of the SeasonsAfter his run on reality TV, Sean went on to serve as district attorney of Ashland County, Wisconsin, and became the U.S. Representative for Wisconsin's 7th congressional district. He married Rachel Campos in 1999, who he met during All Stars. The pair have nine children together. He exited Congress in 2019 when his wife was dealing with “complications” surrounding their ninth child’s birth. Andrew Harnik/AP/Shutterstock
Seasons won: All Stars and Battle of the Sexes 2Eric appeared on Confessions of a Teen Idol after finishing his run on The Challenge. He is married, has a son and works as a health and wellness coach. He last appeared on The Real World: Homecoming in 2021. Araldo Di Crollalanza/Shutterstock; Courtesy of Eric Nies/Instagram
Seasons won: Real World vs. Road Rules and Battle of the SexesLong has hosted multiple episodes of Challenge aftershows and reunions through the years and has worked to cast other reality shows. In 2020, he teamed up with Bunim-Murray Productions and is set to launch a new Challenge series featuring only old-school competitors. The Challenge: All Stars debuted on Paramount+ in 2021. Courtesy of Mark Long/Instagram
Seasons won: Real World vs. Road Rules and The GauntletRoni lives a relatively private life and doesn’t have public social media accounts. She is seemingly married as her last name is now Chance. She has worked at Hearst Magazines as a photo editor since 2006. MTV
Seasons won: Challenge 2000 and Battle of the Sexes 2Dan lives in Nashville and is working on his music career. MTV
Seasons won: Challenge 2000 and The InfernoNow going by Holland, she married Justin Darcy in 2011. They have two daughters. She now works as a senior manager at Deloitte Digital in Denver. Courtesy of Justin Darcy/Instagram
Seasons won: Challenge 2000, The Gauntlet and The InfernoVeronica has continued to appear on seasons of The Challenge and participated in a Challenge special at Universal Orlando in 2019. Courtesy of Veronica Portillo/Instagram
Seasons won: Extreme Challenge, Battle of the Sexes and The Gauntlet 2Jamie worked as the petitions coordinator for entrepreneur Andrew Yang and lives in Illinois with his wife and twins. Courtesy of Scott Yager/Instagram
Seasons won: Battle of the Seasons and The Inferno IIThe Miz is now a professional wrestler and WWE star, competing on Smackdown. He has hosted multiple Challenge reunions and landed his own show, Miz & Mrs., with his wife, Maryse Mizanin, in 2018. The couple has two daughters. Picture Perfect/Shutterstock; MediaPunch/Shutterstock
Seasons won: The Gauntlet, The Inferno, The Inferno II and Fresh MeatDarrell is still competing on the Challenge. He is married, has two children and works as a personal trainer. Courtesy of Darrell Taylor/Instagram
Seasons won: The Gauntlet and The Duel IIRachel is married to Natalie Gee and the couple have three children. She works as a physical trainer at Barry’s Bootcamp in Miami and runs Rachel Fitness. Courtesy of Rachel Robinson/Instagram
Seasons won: The Gauntlet and Battle of the Sexes 2Theo is an actor and comedian who has appeared on Chelsea Lately, Watch What Happens Live With Andy Cohen and @midnight. He released his first comedy special on Netflix in 2016. He also hosts the “This Past Weekend” podcast. Mediapunch/Shutterstock; Courtesy of Theo Von/Instagram
Seasons won: The Inferno and The Inferno IIIAbe married Rachel Missie in 2019 and works in Montana at Soundcolor Studios, which he confounded with his brother. In October 2020, Abe and Rachel announced they're expecting their first child. Their son, Atlas Young, arrived in April 2021. She shared the news that the pair had broken up in September 2021. Courtesy of Rachel Missie/Instagram
Seasons won: The Inferno II, The Gauntlet II and Fresh Meat IILandon is the founder and CEO of Executive Cycling Excursions and is a dental equipment and technology specialist. MB Pictures/Shutterstock; MTV
Seasons won: The Gauntlet II and The DueiJodi is married with a son and they live in Germany. She also runs Sweaty but Ready Fitness. Courtesy of Sweaty But Ready/Facebook
Seasons won: The Gauntlet II and The RuinsSusie hosts the "Brain Candy" podcast with former Challenge star Sarah Rice. She founded the WAVE Podcast Network with her husband. They have one son. Courtesy of Susie Meister
Seasons won: The Duel and Rivals IIWhen he’s not competing on the Challenge, Bergmann lives in Kansas with his wife and dog. He works as a startup engineer for BetaBlox. Rob Latour/Shutterstock
Seasons won: The Inferno 3, The Island and The RuinsDerrick is divorced with one son, living in West Virginia. He cohosts the "Challenge Mania" podcast. Us exclusively announced in January 2021 that Kosinski is engaged to Nicole Gruman. They wed in July 2022. Byron Purvis/AdMedia Newscom/MEGA; Courtesy of Derrick Kosinski/
Seasons won: The Inferno 3, The Island and RivalsAfter competing on the Challenge fresh out of high school, Evelyn attended the University of San Diego then went on to Harvard Law School. Since 2015, she has been working as a fellow for a human rights program in Cambodia. Courtesy of Evelyn Smith/Instagram; Courtesy of Evelyn Smith/Facebook
Seasons won: The Inferno 3, The Island and The RuinsKenny has worked in physical training in New York City ever since leaving the show. He is a brand ambassador for Michelob ULTRA and created STRONG New York health and wellness series. Chris Pizzello/AP/Shutterstock; Courtesy of Kenny Santucci/Instagram
Seasons won: The Gauntlet III and CutthroatTori currently lives in Nashville, Tennessee, and shares two sons with ex-husband and Challenge vet Brad Fiorenza. She works as a sourcing recruiter for Amazon. In October 2020, she married lawyer Dusty Gwinn. The pair welcomed their first child together the following year. Courtesy of Tori Hall
Seasons won: The Island, The Ruins, Rivals, Battle of the Exes, Free Agents and Rivals IIIJohnny Bananas has appeared in more Challenges than any other competitor and plans to continue until he’s physically unable to do so. He hosts NBC’s First Look and joined the cast of Worst Cooks in America in 2020. He began hosting Celebrity Sleepover on NBC in 2021. He dated Big Brother winner Morgan Willett from 2019 to 2021 after meeting on War of the Worlds. Courtesy of Johnny Devenanzio/Instagram
Seasons won: The Duel II and The RuinsEvan resides in New York and is the founder and president of The Bait Shoppe agency. He married in 2016 and has one son. Courtesy of Rachael Kari Starkman/Facebook
Seasons won: Cutthroat and RivalsAfter winning two seasons of The Challenge, Tyler moved to Long Beach, California, where he works in special events at the Long Beach Museum of Art Foundation. Carolyn Contino/BEI/Shutterstock; Courtesy of Tyler Duckworth
Seasons won: Rivals and Rivals IISince her last appearance, Paula married Jack Beckert and the pair have three kids. She lives in New Jersey and works for Power Home Remodeling Group. Courtesy of Paula Meronek/Instagram
Seasons won: Battle of the Exes and XXX: Dirty 30After the Challenge, Camila moved to Oregon. She welcomed her first child, a boy, in July 2020. Courtesy of Camila Nakagawa/Instagram
Seasons won: Rivals II, Invasion of the Champions, War of the Worlds 2, Double Agents and Spies, Lies and AlliesAlthough CT is still competing on The Challenge, in his off-time he lives in Boston with his wife, Lilianet Solares, and their son. The pair's wedding special aired on MTV in 2018. The couple separated ahead of season 36 in 2020 but got back together after filming wrapped. Courtesy of Johnny Hickey/Instagram
Seasons won: Battle of the Exes II, XXX: Dirty 30 and War of the Worlds 2Jordan and Challenge star Tori Deal got engaged during War of the Worlds 2. The pair recorded music together while living in Los Angeles and he also works as an actor, appearing on episodes of The Blacklist and If Loving You Is Wrong. In November 2020, Jordan and Tori announced their split. Courtesy of Jordan Wiseley/Instagram
Seasons won: Battle of Exes II and Rivals IIIAfter leaving The Challenge, Sarah launched a podcast, "Brain Candy," with Susie Meister. In 2019, she announced that she and her husband had split after four years together. Courtesy of Sarah Rice/Instagram
Seasons won: Battle of the Bloodlines and VendettasWhen she’s not competing on The Challenge, Cara Maria lives in Montana and creates Armor Up! workouts. She lives with boyfriend Paulie Calafiore. MTV; Courtesy of Cara Maria/Instagram
Seasons won: Invasion of the Champions and Final ReckoningWhen not competing, Ashley lives in Las Vegas and spends her time traveling. Courtesy of Ashley Mitchell/Instagram
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