Rupert Boneham

Pearl Islands, All-Stars, Heroes vs Villains, Blood vs Water

To celebrate the 40th season of Survivor, we’re counting down the 40 Most Influential Survivors to ever play the game. Because Survivor is a game, a tv show, and a rabid fandom, we’re taking all forms of influence into consideration for this list. Go here to view the criteria we are using to determine what qualifies for the list. Note: this list is presented in chronological order and there will be spoilers for various Survivor seasons. Rupert Boneham is the 9th entry in this series.

In the beginning, Survivor was designed as a society-building exercise that also contained game elements. Jeff Probst likes to suggest that the show was (and is) a social experiment that reflects society. And the earliest seasons of the show generally tried to cast a group that would cover as many demographic categories as they could- age, race, geographic locations, sexuality, income, etc. The show also highlighted its locations, forcing Americans to play the game and survive in various far-flung locales.

But in season seven, the show tried something a little different. With the season set in the Pearl Islands off the coast of Panama, the show focused on a theme related to the location: the rich history of piracy in the region. Thus, the opening scene of Pearl Islands– still perhaps the greatest start to a season premiere the show has ever had- is a marooning. Thinking that they were going out for a publicity photo shoot, the players are informed by Jeff Probst that they have just a few moments to gather up as many supplies as they can before jumping into the water and swimming to shore in whatever clothes they had worn for the photo shoot. Once there, they’d have to wander into a local village to haggle and barter for whatever they thought might help them in the game.

It’s in that local village that we first meet Rupert. As the other players are desperately trying to invest in items that will help themselves and their tribe, it quickly becomes clear that the thing that Rupert is most heavily invested in is the theme of the season. Probst just told them on the boat that this place is known for piracy, so Rupert decides to do the thing that pirates are famous for: stealing shoes.

Wait.

(Checks notes.)

Nope, that’s correct. He stole shoes. Just like a pirate!

The cast of Pearl Islands was loaded with characters, and Rupert became its breakout star. With the tank top of a hippie, the skirt of a tribemate (the jeans he began the game with caused chafing in his nethers), and the body of a Survivor podcaster, Rupert was a huge hit with Survivor fans. In a season surrounded by a murderer’s row of man meat – chiseled, handsome studs like Andrew Savage, Osten Taylor, Burton Roberts, and Ryan Opray – Rupert got to tell the audience how being surrounded by these athletic stud bros reminded him of being bullied as a kid. Rupert became the lovable, rootable underdog. Later, he would beat some of those handsome jocks in challenges, including those that relied on strength. It made for a great narrative, and the audience ate it up.

Rupert was immediately asked back to play in All-Stars, the first time Survivor ever featured returning players. He played against most of the biggest names in the game to that point (and also Boston Rob and Amber), and made it to the final four of that season. At the live finale of that season, one player was selected by fan vote to receive a million dollars. The fans chose Rupert. Even though he lost the popularity contest that is the actual game of Survivor, he won the literal popularity contest instead- and received the same reward as Amber. This was a real, actual thing that happened.

All-Stars would not be the last time Rupert was invited back to Survivor. He came back for both Heroes vs. Villains and Blood vs. Water, and he continued to implement the lessons he’d learned in his very first season: if you want camera time, steer hard into the season’s theme- even if you aren’t very good at it. In Blood vs. Water, he gave the show what it wanted by willingly taking his wife’s spot on Redemption Island after she was voted out. But to hammer home the moment, he made sure to note “that’s my blood” when speaking of his wife, which does not mean what he thinks it means! In Heroes vs. Villains, he relished the chance to call the other tribe villains, as though they were somehow lesser human beings than his tribe of noble heroes. (It should be noted- mostly because I’m an asshole and feel like noting it- that many of the other players he has played against have given the impression either explicitly or implicitly that Rupert is obnoxious and insufferable. The fact that he ran for governor as a Libertarian should honestly be enough evidence to support this).

The lessons Rupert learned about how to get screen time have been absorbed by legions of Survivor players hoping to see more of themselves on television. If you want to see yourself on TV, you have to give the show what it wants. You’re getting treated to an Applebee’s meal? “Holy shit I would stab an entire orphanage for one of their signature dishes that I definitely know but cannot currently think of” is the confessional that gets you screen time. Production also wants players to help market the show itself. This is why modern Survivor fans get treated to confessionals that begin with “As a Goliath…” or “As a white collar…”, because the show desperately wants players to reinforce the season’s contrived theme.

Rupert’s other lasting legacy was the underdog story they got to tell in Pearl Islands, and the show continued to try to cast a new Rupert- an everyman underdog that they could sell to the mainstream audience. They found one in Vanuatu– he even won the game!- but he lacked Rupert’s screen presence, so the show kept trying. To say their attempts at finding a new Rupert have had mixed results would be far too generous; they’ve mostly just fucked this up. The list of would-be Ruperts is long and ranges from underwhelming to merely acceptable: Billy Garcia in Cook Islands, Lunchlady Denise in China, Papa Smurf in Fiji, Jimmy T in Nicaragua, Matt Bischoff in Caramoan, Dan Foley in Worlds Apart, Kyle Jason in Kaoh Rong, and Bret LaBelle in Millennials vs. Gen X to name a few.

Despite the many attempts, Survivor has failed to recapture that Rupert magic with anyone other than Rupert, which probably explains why he’s been asked back so many times. They even cast him in The Amazing Race, which is how I’m able to bless your day with this gem:

If you listen to just the audio of Rupert riding this elephant, it sounds like a really sad porno. #AmazingRace pic.twitter.com/ZyjGB8L8vb

— Ryan Kaiser (@Ryan__Kaiser) April 25, 2019

Who else made the list?

You can see each entry on the list by clicking this link.