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The 20 Best Episodes That Defined The Challenge Legacy
20 Aug
Summary
- Iconic moments include Bananas Backpack and Ashley's prize theft.
- Diem's resilience and courage captivated viewers and castmates.
- Jordan's bold move against Bananas showcased his fearless spirit.

Entertainment Weekly has ranked the 20 most defining episodes of The Challenge, showcasing moments that have solidified the show's legacy. These selections highlight the intense rivalries, shocking betrayals, and incredible displays of resilience that have captivated audiences over the years.
Iconic moments include Johnny Bananas' unforgettable 'Bananas Backpack' elimination against CT, where CT carried Bananas to victory. Ashley Mitchell's decision to keep the entire prize pot from her partner, Hunter, in Rivals III also remains a defining, albeit controversial, event.
Diem Brown's appearance on The Duel, shortly after completing chemotherapy, exemplified her strength and courage. She bravely removed her wig during a challenge, a moment that showcased her resilience and earned her widespread admiration.
Jordan Wiseley's bold move to intentionally face Johnny Bananas in an elimination on Free Agents, despite being a perceived underdog, marked a pivotal point in his career and the show's lore.
Other notable episodes feature Coral Smith's defiant declaration, Laurel Stucky's controversial elimination win, and Derrick Kosinski's grueling pole wrestle with Joss Mooney, demonstrating the show's capacity for both extreme drama and athletic prowess.