The Funny 115 - The Third One

#98. The Problem With Government Jobs
Redemption Island - episode 2

I'll be the first one to acknowledge that Redemption Island is not a very popular season.   Whenever people rank their favorite Survivor seasons, unless you are a Boston Rob fan, or unless you are Jeff Probst, it almost always winds up at the bottom.  In fact, at the time of me writing this entry, I can't imagine there is another season of Survivor that people would rank lower than they rank Redemption Island.  

Basically, if Survivor were a line of Turbo Man action figures, Redemption Island would be Booster.

Now, I'm not going to sit here and rave that Redemption Island is an amazing season or anything, it's not.  But I AM going to point out that there are a couple of fun things going on throughout the season that make it better than you remember.  Which is a lot more than I can say about a truly horrendous and unwatchable season like... oh I don't know... how about One World.  

Oh, I haven't started bashing One World yet?  Well get ready.  It's coming.

Literally the third greatest moment in One World

From a comedic standpoint, the thing that Redemption Island has going for it (especially in the first couple of episodes) is that it features one of the greatest camera hogs in the history of Survivor who isn't named Coach.  In fact, you might know him better as "The Specialist."

That's right, I can only be talking about the one and only former FBI agent, Phillip Sheppard.  Who really is the star of the first couple of Redemption Island episodes.

The Specialist

Now, again, I'm not going to sit here and tell you that Phillip is a great character, or that he is even a beloved character.  By the time he came back and played again in Caramoan, I was as sick of him and his dumb nicknames as you were.  

Jessum Herring something something

Buuuuuuuutt, I happen to think it would be a travesty if people think he was awful all the way back at the beginning of Redemption Island.

Remember, Redemption Island didn't start bad.  It only became bad.  The first few episodes where the Ometepes were all trying to figure out Phillip were actually pretty fun.  

Especially because you had this guy always commenting on them

So let's go back and relive the birth of Phillip Sheppard, the Specialist, and let's be reminded why Boston Rob is one of the greatest Survivor narrators of all time.  You might not like the guy as a player or as a winner* or as any sort of a Survivor icon, but as a confessionalist he has always been right there at the top with the best of them.  His interactions with Phillip in Redemption Island are some of his best.

*4 tries

Still thinks the General has a little sausage

Okay, so it is day one of Redemption Island, and Boston Rob has stepped out of the helicopter to get a new look at his tribe.

I sweah to god I hope I'm not on the buffoon tribe again

And sure enough, there is one eccentric older guy in pink undies who is quickly going to become the centerpiece of all things Ometepe.

Thank you for your service

Phillip comes back to camp with the Ometepes, and he immediately does everything he can to become as overbearing as possible.  

By the time the first day is over, he has annoyed Francesca by informing her that she doesn't shovel correctly.

Oh god, who is this douchebag?

He has annoyed Andrea by informing her that she doesn't use a hatchet correctly.

 You know, I grew up on a farm.  I kinda know how to cut down a tree.

He talks over people, he doesn't listen to people, all he does is basically walk around and micromanage everyone and get on everyone's nerves.

He also does this while wearing nothing but a saggy bottom pair of pink undies, which doesn't help

By the end of the first day, Phillip has annoyed just about everyone.  The girls all hate him, because he talks down to them.

He walks around in his pink panties all day, which is not exactly what the other players want to see when they are trying to build their home.

He basically strongarms Francesca and Kristina into being in an alliance with him, just because he is Phillip and because he is a special agent, and because he knows everything about everyone.

"How did I get stuck with the old annoying guy in the droopy fuchsia briefs?"

"Did I mention that we're in an alliance together?  How awesome."

Everyone on Ometepe pretty much hates Phillip by the end of the first day.

*angry sigh*

"He's such a spaz about keeping his mouth shut.  He's a spaz about everything if you really want to know the truth."

"He's so annoying.  He's so weird."

The only person who seems to like him at all is our old dear friend, Boston Rob.

Why?  Well partly because Phillip has a strong work ethic, and Rob appreciates people who have strong work ethics.

But mostly I would say it because I think Rob is a comedian.  And Rob is very good at picking out people who are not threatening and who he thinks will amuse him.

Even though Phillip is a close-talker, he might actually turn out to be fun

"Phillip is a piece of work.  I mean who comes on Survivor and wears pink tightie whities?"

"With his stuff just hanging out and, you know, just floppin' around everywhere."

"It's not only disturbing, it's actually disgusting."

"It's like, your dad should have bought a new pair like, months ago."

"You don't want your friends comin' over to play and seein' that."

So here we go through the first episode.  Phillip has strongarmed Kristina and Francesca into a 3-person alliance.  Meanwhile, neither one of them can stand him.   Pretty much no one can stand him.  The only person who finds Phillip amusing at all on this tribe is Boston Rob.

"The specialist thinks he is runnin' the show but the Specialist is just one big windbag."

And it is at his first Tribal Council that the legend of Phillip Sheppard, the Specialist, is officially born.

The Specialist, ready to take down his enemies and/or chase a squirrel

So we go to Tribal Council and, as pretty much expected, Phillip is a disaster.

He talks when he isn't supposed to

He calls out his own allies, Francesca and Kristina, and he tries to get them voted out

He just rambles on and on and on and the other players realize very quickly that this guy is unhinged.

Oh yeah, and he also has dry mouth so he can't figure out how to pronounce "Francesca."


For pretty much the entire scene, the camera keeps panning to the other members of Ometepe as they wince in shock at how bad Phillip is at playing Survivor.

Except, of course, for the one guy who finds Phillip's entire Tribal Council strategy hilarious.

Oh man, this is hilarious


And hey, look at this.  Even Probst gives a big goober at one point because Phillip is so ridiculous.

I am so going to use this picture a lot in this countdown

At the end of the night, Phillip has gone on a rampage (against his own allies), he has outed the fact that his best ally is holding a hidden immunity idol, and he has basically made a fool of himself repeatedly every time he opened his mouth.  It really was one of the craziest Tribal Councils I think of during this stretch of seasons (21-30).  Keep in mind that this was one of the most talked about Survivor premieres in history the day after it aired, and it was because of Phillip and what a blowhard he was.

Oh yeah, and then he apparently votes Frankekwa out in Greek.  What is that, a fucking sigma?

So we go back to camp, and everyone is aware now how nutty Phillip is, and how unhinged he is.   Kristina even goes so far as to suggest that "there might be some instability there," which is one of the all time great Survivor understatements.  

It doesn't help that, the next morning, he decides to go on a crab hunt while only clad in his undies

The Ometepe tribe watches him hunt a crab and they just stand there and laugh

Phillip catches a crab.  HOO HAH!

And now we come to the best part between Phillip and Boston Rob.

This is where Phillip approaches Boston Rob and he offers to be BR's number one ally

Rob is fine with Phillip as an ally, but only under certain conditions.  Mainly because Phillip is like a child, and Rob doesn't trust his ability to ever keep his mouth shut.  So Rob will only ally with The Specialist under one condition.

I basically have to tell him who we're going to vote for right before we leave for Tribal.  He can't know any sooner than that, or else he'll blab it.

Rob spills out the details to the Specialist in a side conversation.

This is a followup to a conversation that the two of them had right after the first Tribal Council, when Frankekwa went home.  Phillip has already told Boston Rob that Rob controls his vote.  Phillip will do anything Rob says.  At this point he basically Rob's little manservant.

The night before, right after Tribal Council

Phillip summons Rob to go speak in the woods.

This was Phillip's bizarre offer to do anything Boston Rob tells him to do.  

And I love this next shot, which shows exactly how much Rob was into this conversation, and how much he cares about "restoring Phillip's honor."

Hey Natalie, can you make me some of that crispy rice?

Okay, so there is our setup for Phillip.  He is bizarre.  He is unhinged.  He is completely unpredictable and weird.

He makes strange allusions and faces in his confessionals.

He does these odd Phillip things around camp.

They all know him as this strange "former federal agent" who they all think is insane.

"Any time Phillip says anything, anything at all, I pop wood."

And this is where Boston Rob drops one the all time great Boston Rob confessionals.

He is talking about the first Tribal Council, and about Phillip being nuttier than a fruit cake, and here's how he describes it.  

This is why I always say that Rob is a great narrator.

"I know for a fact that Phillip and Christine were lyin'."

"But it doesn't take a genius FBI man to figure that out."

"All you have to do is look at their faces and watch their lips movin'."

"This guy, Phillip, FBI whatever, special agent."

"He is a piece of work."

"He told me that I own his vote for the rest of the time he's here.  Until he goes to Redemption Island."

"I don't know if he's delusional..."

"I think he's a good hearted guy, I do."

"He just might not all be there."

Annnnnd, the punchline.

"Let it be a lesson to you."

"Government jobs?"


** Thanks to Ryan Weiss and Will Holston for the Ferris Bueller/Brad Culpepper picture **

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