The 115 Funniest Things to Ever Happen on Survivor

#68. Rupert Boneham
Pearl Islands - Multiple Episodes

That beard!

That face!

That skirt!

That growl!

Those big, sad Basset Hound eyes!

That roar!

Who else could I be talking about? That's right, it's the one and only Rupert Boneham. Or as I like to call him... the single most unique person ever to be cast on Survivor.

I know you are probably sick of the Rupert media overkill. Heck, so am I. And I bet Rupert pretty much is sick of it too. But there's no denying the fact that Rupert was a star and Rupert brought the goods in every single episode of Pearl Islands. When people get overexposed in the media, there's generally a good reason for it. It's because they were interesting to watch the first time around. And I'll be the first one to stand up and say that Rupert kicked ass. Rupert Boneham was a dynamite Survivor character. Always was, always will be. The entire Pearl Islands season revolved around him, he factored into just about every single event during the season, and he had that certain special trait that all my favorite characters have ever had.

Know what it was?

Simple. He was entertaining without trying to be. Rupert made us laugh, he captivated our attention, he stole every single minute of camera time... yet he wasn't even trying to do it. Rupert thought he was just this fat little kid playing pirate. But somehow he ended up being funny without trying to be funny. He was entertaining without trying to be entertaining. He was the hero without trying to be the hero. And that's why he is arguably the most memorable and entertaining (and beloved) Survivor of all time.

In other words, you couldn't have made up a character like Rupert if you had tried.

There was one Rupert trait that really stood out for me, however, and it's the reason he made it to #68 on this list. And it's something that not a lot of people remember. Oh sure, you might think about Rupert and remember the beard. Or the tie-dye. Or the bipolar shifts in temperament. But do you remember the way he talked? Do you remember the quirky way he phrased things?

It all started in his Pearl Islands bio page at That was the first time I realized this guy didn't always speak the same language as the rest of us. Because right there under his favorites, written in Rupert's own weird phraseology, was this wonderful gem:

Favorite Non-Alcoholic Beverage: 2 percent Cow's Milk.

Cow's milk? COW'S MILK?? Who the fuck has to specify that he's talking about cow's milk? Is there a large society of goat milk drinkers out in Indiana? Are people drinking penguin milk? What the hell? So right away I knew that Rupert was going to be unique. Any person who has to specify that he's talking about cow's milk is somebody I can fully get behind as a Survivor character.

And I was not to be disappointed.

Remember these oddly phrased Rupert-isms, from the first few episodes of Pearl Islands? It was almost as if English wasn't really his first language. Because if he wasn't making up sentence structure, he was making up words. And if he wasn't making up words, he was making up inflection (ala Christopher Walken). And if he wasn't doing any of that, sometimes he was just growling for no apparent reason. But no matter what he did, it all boiled down to the same thing time and time again: No matter what he said, this Rupert guy was just entertaining as all hell whenever he opened his mouth.


* "And so I stole. I stole for da Drake."

* "These jeans were eating my CRRRRRRRROTCH!"

* "Jon's like one of my kids back at home. He just pops off, about STOOOOOOPID stuff."

* "We had a feast, and we had a big ol' honk'a LAAAAAAAAAMB."

* "A saltwater catfish? I didn't know they made such a animal."

* (from All-Stars) "I caught a fish. I poked it with a stick, I caught a fish!"

There are plenty more Rupert-isms out there, but these were the ones that particularly warmed my heart. I especially liked the one about "a honk'a laaaaamb." That quote could not have been said by anyone else. But besides all the quotes above, there were plenty of other "Rupert moments" that warrant mentioning during Pearl Islands. Remember Rupert's giant emotional swings? He would go from completely happy to completely sad. There was no such thing as an emotion in the middle. It was all or nothing with him, at all times (especially when he was upset about something). Remember when he nearly cried at the third Drake tribal council? Keep in mind that he wasn't just doing this for the camera. Rupert was literally about to start crying.

Rupert had big highs. Rupert had big lows. He also let loose the most spectacularly mournful sighs of despair. Oh, and plus he had weird quotes. But one of my favorite Rupert moments came in the ninth episode, when Burton didn't pick him to go on reward. Rupert was so upset that he didn't get picked that he went on a little mini-rant. But the funny thing was that (for once) he didn't do it out loud. No, he decided to rant to himself, under his breath, kind of like Milton in the movie Office Space. It was just the funniest thing. Here's Rupert, pissed off at the world and at Burton in particular, and he's mumbling threats under his breath like the way Milton talked about his red Swingline stapler. My wife and I always refer to this as Rupert's "Milton tantrum." It's one of our personal favorite moments of the season.

"(mumbling) That'll teach me to do nice things for Burton anymore. See if I take him on any more rewards. They better not take my red Swingline stapler. I was told I could listen to my radio at a reasonable volume. I'll burn this place down right now."

So anyway here's to Rupert Boneham, and all the quirkiness, quotes, and eccentricity he brought to the show. It's a shame that media overkill has turned a lot of fans against him over the past few years, because Rupert is and always will be a Survivor superstar. In fact, his boot episode might be the single best Survivor episode of all time. So he makes the list at #68 just for being himself. There's no way he could have been anybody but 2-percent-cow's-milk-drinking Rupert Boneham.

"So much for my dreams."

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