Bananas has made an actual career out of being a Challenge mainstay, and he'll step on just about anyone to earn his "salary" — which is now the highest amount that any competitor has earned on this franchise. Before Total Madness, he had not made it to a final since he stole the money from his partner Sarah Rice in Rivals III – leading many to believe he was cursed. But he put all that curse talk to bed once and for all by winning a record seventh time in his 20th season, making him the most decorated Challenge champ of all time. And he’s not done yet.

No. of Seasons: 20

Seasons Won: 7

Trips to the Final: 9

Elimination Wins: 10 of 24

Total Winnings: $$1,184,720