Tyler was the second male eliminated on both his first season (the Duel 1) and second season (Gauntlet 3). In those two seasons, his highlight was eliminating Johnny Bananas in “I Can”, a game where players bet on whether or not the other could lift a copious amount of watermelons. Tyler made an awful move by picking the only person who would have aligned with him, and then made another poor choice by choosing elimination juggernaut Derrick for his second elimination. On Gauntlet 3, he fell for Ryan Kehoe; meanwhile, Ryan regretted making out with Tyler and made fun of him behind his back.

When Tyler showed up for Cutthroat, expectations were low. However, an unexpected 15–30 lb weight gain (from eating), end up turning Tyler into a powerhouse. Tyler becoming a 6-foot tall man with a 200 lb frame, made him an intimidating presence. Add in the fact he was a well-educated collegiate swimmer who ran Iron Man races for fun, and he was now one of the biggest all-around talents in Challenge history. Tyler became a vital member of the Red Team on Cutthroat and eliminated Johnny Bananas and Derrick Kosinski. It was an extremely impressive considering Derrick had won his three previous seasons, and Johnny Bananas would go on a stretch where he’d won his two previous appearances and then his two following seasons as well.

On Rivals, he and Bananas paired up and were the most consistent team in the daily challenges. In the end, they won a critical elimination against CT and Adam, where Tyler took two gigantic hits from a fully powered CT. He proved himself the most by finishing and winning the intense Rivals 1 final despite having Food Poisoning.

Tyler went from two time early exit to two-time Challenge Champion. Sometimes we should wait before we call a competitor a flop.

2 Johnny Bananas

If you told a Challenge Fan in 2008–2009 that in a decade that Johnny Bananas would be a 6x Champion and recognized by a significant portion of the fandom as the greatest player in Challenge History, they’d have the same reaction as Christopher Lloyd in Back to Future learning that Ronald Reagan became the President.

Johnny Bananas was never bad at the Challenge. However, during his first five year stretch on the show, he was at best a B+ player. Johnny lived largely in the shadow of Kenny and Evan. He was able to feast from their riches and pick up two titles from the Island and the Ruins, seasons where he didn’t do much aside from being Kenny’s friend. Hell, even Derrick wanted to beat the shit out of Johnny at some points. Bananas was also in the shadow of more prominent stars like CT and Wes. He wasn’t the winner that Landon and Darrell were. He didn’t have the fan support that players like Derrick and Brad had.

When Cutthroat arrived, it was Johnny’s time to play without either Kenny or Evan. What happened? His team failed in all the challenges, and he got backpacked by CT. Even when Johnny and Tyler won Rivals 1, the edit never celebrated them. The attention was on Kenny, Wes, Evan, CT, and even Mike Ross more than he and Tyler. At the reunion, they got snubbed for more exciting topics. Once Evan and Kenny were forced to leave, it was then Bananas rose and became a legitimate superstar (which is wild since he was already a 3x Champion).

On Exes 1, he got partnered with an elite player in Camila. Together they were the best team in daily challenges, won a crucial final elimination, and took home the win in the final. Not to mention, they had a rocky relationship on the show, and Bananas began to mimic many of Kenny’s phrases and idiosyncrasies. He’d continue to be a significant figure on Rivals 2, and then have one of the all-time great wins on Free Agents. He’s created a bigger star status and been a major face on Bloodlines, Rivals 3, Vendettas, Final Reckoning, etc. Since then, he’s been featured on the Bill Simmons Podcast, gotten a job hosting a show on NBC, was granted a spot in the Miz’s fantasy football league and gets paid close to six figures just to appear on the Challenge.

1 Cara Maria Sorbello