Every Season of The Challenge, Ranked: #24 — The Island

Michael Alvey
15 min readApr 8, 2022

Location: Boca del Drago, Panama

Host: TJ Lavin

Aired: 2008

Champions: Evelyn, Johnny, Kenny, Derrick

Overall Thoughts: I’m sure many people are wondering why I have this season so high.

While there’s a lot about this season I don’t like — mainly the format and the bad treatment of some of the women — there’s also so much I love about The Island.

This is almost a Real World season masquerading as a Challenge season. As a fan of messy drama, there’s few better in that category than The Island.

The booze was running rampant, and the lack of protein turned the cast into animals (looking at you, Dunbar). Sometimes it was ugly, but it was entertaining as hell.

Besides the messiness, the Johnny vs. Evelyn storyline is in my opinion the best season-long narrative in Challenge history.

For Evelyn to be against Johnny the entire season, then be forced to team up with him in order to win the final…it doesn’t get much more compelling than that.

The Island spawned so many future storylines, most notably the Kenny vs. Wes feud that came from Kenny hooking up with Johanna.

No matter how you feel about this season, there’s no denying this — it’s one of the most important in the history of the show.


  • Kenny hooking up with Johanna
  • Abe getting stung by wasps
  • Dan snapping on Dave
  • Abe trying to quit, and still almost winning the vote-off against Bananas
  • TJ berating Dave for quitting and Ashli for putting herself into the Face-Off with an injured foot
  • Paula getting smoked in the Ball Buster Face-Off
  • “Take your telescope and shove it up your fucking ass”
  • Evelyn giving the greatest speech in Challenge history, calling out “The Family” and stealing Johnny’s key
  • The Dan and Robin “limp dick” fight
  • Kenny and Johnny cutting a deal with…