The Challenge · Season 16
Real World/Road Rules Challenge: The Island
Champion: Derrick Kosinski & Evelyn Smith & Johnny "Bananas" Devenanzio & Kenny Santucci
Season overview
Location
Boca del Drago, Panama
Aired
September 10, 2008
through November 5, 2008
Episodes
9
Players
20
Host
T. J. Lavin
Cast type
Returning players
Cast
| Place | Player | Result |
|---|---|---|
| 1st |  Derrick Kosinski Road Rules: X-Treme | Winner (2) |
| 1st |  Evelyn Smith Fresh Meat | Winner (2) |
| 1st |  Johnny "Bananas" Devenanzio The Real World: Key West | Winner |
| 1st |  Kenny Santucci Fresh Meat | Winner (2) |
| 2nd |  Jenn Grijalva The Real World: Denver | Runner-up |
| 2nd |  Paula Meronek The Real World: Key West | Runner-up |
| 2nd |  Robin Hibbard The Real World: San Diego (2004) | Runner-up |
| 2nd |  Ryan Kehoe Fresh Meat | Runner-up |
| 3rd |  Abram Boise Road Rules: South Pacific | Eliminated |
| 3rd |  Ashli Robson The Real World: Sydney | Eliminated |
| 3rd |  Cohutta Grindstaff The Real World: Sydney | Eliminated |
| 3rd | Colie Edison The Real World: Denver | Eliminated |
| 3rd |  Dan Walsh Road Rules: Viewers' Revenge | Eliminated |
| 3rd |  Dunbar Merrill The Real World: Sydney | Eliminated |
| 3rd |  Johanna Botta The Real World: Austin | Eliminated |
| 3rd |  KellyAnne Judd The Real World: Sydney | Eliminated |
| 3rd |  Rachel Robinson Road Rules: Campus Crawl | Eliminated |
| 3rd |  Tonya Cooley The Real World: Chicago | Eliminated |
| 3rd |  Tyrie Ballard The Real World: Denver | Eliminated |
| 4th |  Dave Malinosky The Real World: Hollywood | Quit |