One of the big surprises in season 4 was the reveal that "Good old fun time Hurley" might indeed be (duh dun DUH!)... "special." The relationship that this is most tied to has got to be one of the most unlikely buddie pairings in LOST history: Hugo "Hurley" Reyes and Benjamin Linus. I think it's pretty obvious what this column is all leading to, but that's for the end. Let's start at the beginning.
Hurley is the main cast member Flight 815 passenger whose life pre-Island was most obviously a precursor to events on the Island, I am going to argue, because of his entanglement with the Numbers, which through both the radio tower transmissions and their presence on the Swan hatch door and as the numbers being entered in the Swan computer, are clearly tied deeply to Island mythology. No other passenger on Flight 815 had anything like that connection *before* they landed on the Island. Not that we know of, anyway. My personal theory is that like Walt and Aaron, Hurley was a "special" child, and Cheech (his dad) was aware of this, and had ties to some sort of Island-related group (probably DHARMA, or maybe Widmore's people). On the other hand, via the flashbacks, it would seem like Hurley was one of those people who "wasn't supposed" to be on Flight 815, because of all the obstacles that he had to get through at the Sydney airport to get on the plane. A-ha, *but*, the airport was also chockful of the Numbers as he was making his way there, which one could (and I will) argue were a sort of guidepost leading him to the plane, as a sort of numerological guarantee that he would indeed follow his destiny towards landing on the Island.
Okay, I've set up Hurley's earliest roots in the mythology. Now, let's follow his ties to Ben. While Ben, as "Henry Gale", was being held in the Swan station's armory, Hurley didn't really have much interaction with him. But, Ben's captivity was soon to have a very important impact on Hugo, as a deal was struck with Michael, which led to the shooting death of the other 50% (the really unpopular half) of the Island's Latin-American population, and more importantly, Hugo's hot new crush, Libby. Now, as is pointed out to Michael in season 4, no one *told* Michael to kill Libby, but he did it as part of his deal to free Ben, so Ben is at least tangentially involved, if not technically guilty, in Libby's death.
The first direct tie between Ben and Hurley comes when Michael returns to the Beach Camp, with a list of four Losties he's to bring to the Others: Jack, Kate, Sawyer and Hurley. Of those, Hurley's distinction was that he was not hiking off to spending a big chunk of season 3 in captivity. Nope, the Others just wanted to be able to send Hurley back to tell the remaining Losties to leave them alone. Or that, at least, is what we're supposed to think. Considering that our four Losties were knocked out by blow darts, we don't really know for sure what happened on the way to them waking up at the Pala Ferry to see Ben giving Michael the boat and Walt. Perhaps Hurley was actually taken to Room 23 for some quick brainwashing and/or evalutation? Just a theory, but possible, yes?
Ben and Hurley didn't have much direct interaction in season 3, but in "Tricia Tanaka is Dead", Hurley discovered the DHARMA van which we later discovered was actually the vehicle in which Ben killed his father, who was the skeleton named Roger, Workman, which Hugo confused as being his full name. Hurley was led to the DHARMA van by Vincent, dog of doom, who brought to him Roger's arm (in his mouth, ewww). If you interpret Vincent as being a pawn of the Island (and the "So It Begins" mobisode certainly supports that theory), then what was going on was that the Island wanted Hurley to find the van.
And what did Hurley do with the van? Besides lifting a few spirits, the van was instrumental to Hurley's next tie to Ben, which is that he steamrolled onto the beach, killing Ryan, which allowed Sayid and Sawyer to get the upper hand, leading to the deaths of Jason and Tom. With their deaths, and with all those other Others killed the previous night, the physical manpower of the Others was cut by drastic numbers, disabling their ability in season 4 to mount as much as a challenge to Keamy's Krew as they would have been able to otherwise. This also leads to a fairly hilarious scene in which Hurley uses Tom's radio to transmit, "Attention, Others. Come in, Others. If you're listening in, I want you to know that we got you bastards. And, unless the rest of you want to get blown up, you best stay away from our beach!" In Hurley's eyes, he saved his Lostie friends. Yay, Hurley.
Soon after, however, Hurley learns that another of his close friends, Charlie, died through indirect involvement of Ben, through his orders to Mikhail to protect the Looking Glass station. That was the bad news. The good news was that he was told the Freighters were coming to rescue them all. And so, the Losties at the beach headed inland that night to rendezvous with Jack's entourage, and this is where the really interesting seeds of the Ben/Hurley relationship start. Falling behind the group, Hurley gets a bit lost, and stumbles onto Jacob's cabin, seeing Christian Shepherd inside and that same strange eye that we saw flashed at us in "The Man Behind the Curtain." Hurley, of course, freaks out. Hurley runs in a different direction, and there's the cabin... again. He closes his eyes, and the Cabin is gone.
When the time comes later that night for everyone to split into different camps, Hurley is the first to cross over to join Locke, a decision he regrets in the future. Ben asks Jack's permission to go with Locke, to which Jack says, "He's all yours." On the way to the Barracks, Locke announces that they have to make a side trip to the cabin (so he can try to get orders from Jacob), which perplexes Hurley, who says he saw the cabin back some other way. The look on Ben's face when he hears that Hurley saw the cabin is priceless. Clearly, the ability to see Jacob's Cabin is not something that is universal on the Island. Hurley tries to talk his way out of admitting that he saw the cabin, but Ben is obviously not fooled.
Like the rest of Locke's group, Hurley settles quickly into the pleasant domesticity of New Otherton, bunking with Sawyer, with whom he is playing horseshoes in the yard when they see Ben walking along, carrying blankets (a nice visual reference to what Libby was doing when she was shot), who they had thought was being held as a prisoner for being, you know, one of the bad guys. Ben says, "See you guys at dinner", which gives "The Other Woman" an awesome little closing line.
Hurley is playing RISK (a more appropriate board game for that moment, I can't think of) with Sawyer and Locke when the phone rings, with a recorded voice announcing that the security fence had been breached (presumably the code that Alex entered was one that would both lower the defenses and trip the alarm). With Sawyer outside saving Claire, Ben and Hurley argue about whether to let him back in the house. Then, later, when Ben uses the strange things in his basement to call on Smokey's help against Keamy's Krew, Hurley quickly puts two and two together, asking Ben if he called "that thing." Yes, yes he did.
Hurley is recruited by Ben to join him and Locke on that belated trek to Jacob's Cabin they've been hunkering to do for the whole season. Hurley comes up with a fairly sound theory about why it is the three of them who are have been able to see the cabin: they're the craziest guys on the Island. There hadn't been much evidence that Ben was crazy until very recently, in "The Other Woman", where we saw how unhinged Ben got about his obsession with romantically trapping fair Juliet. Hurley didn't know about all that, but he probably figured the leader of the "evil" Others had to be crazy, right? Arriving at the mass DHARMA grave, Locke reveals to Hurley what happened to all those people: Ben. Okay, now, maybe Hurley had grounds to think Ben was crazy. But Ben explains something we didn't know yet, which is that the decision to purge the DHARMA Initiative was made by the leader of the Others, but that leader was not him. Which, of course, leaves us with yet another mystery: who preceded Ben? Jacob? Alpert? Widmore? Someone else? Someone we know?
And now, we come to one of the most awesome scenes of season 4, or possibly the entire series. First, however, Locke offered Hurley the chance to leave the trio and return to the camp, which Hurley refused (arguing reasonably that he probably wasn't safer alone in the jungle), which led Ben to congratulate Locke on his manipulative skills. We've seen lots of evidence that the Others prize mind games, for sure. As Locke heads into Jacob's Cabin alone, the former chosen one, Ben, is left to sit sort of dejected and bored with his unlikely new traveling companion, Hurley. And then, Hurley pulls out an Apollo candy bar, which he offers to share with Ben (who accepts). Ben and Hurley sharing candy. LOST at its finest!
The next day, our trio heads toward some high ground, and Ben lifts a rock to reveal a DHARMA tin box, in which there is a mirror for communicating with someone (Alpert and the Others) up high, and a pack of saltines, which Hurley digs right into, prompting Ben to remind him that those crackers are 15 years old, which doesn't seem to much faze Hurley. He's a big guy, he needs carbs!
After the trio reaches the Orchid, Ben and Hurley go their separate ways, as Hurley leaves with Jack and Sawyer, on his way to becoming one of the Oceanic Six. But, we know that Ben and Hurley are likely to have a lot of interaction in the future, as Ben's new best lackey, Sayid, rescues Hurley from the mental institution, and Ben tells Jack that they *all* have to back to the Island, which includes Hurley. So, whatever special connection Hurley has to the Island still has time to be manifested, will probably come into play in season six, when the Oceanic Six is most likely to return to the Island. And Ben is instrumental to all that, so we still have chances of more Ben/Hurley hilarity. Maybe Hurley will introduce Ben to his mom and Cheech!
P.S. I thought this particular connection was fairly minor, but as it turns out, when I actually got into writing about all the connections between Ben and Hurley, it surprisingly was quite complex!