First of all, I’d like to discuss the general tone of the flick. I don’t think will (or should) go the slapstick parody route (think The Brady Bunch), rather play it straight. This is a post-Lost pop culture era we’re dealing with, and while Gilligan planted the castaway flag first, the landscape has changed. Lost will hold an indirect influence on the story. Sure, it won’t go the sci-fi mystery route, but in the great strides we’ve made in the past 45 years of TV and film, slapstick wouldn’t be the appropriate route to go. Turn up the smart, sly and dry, and you’ll have a damn good script, and assembling the right actors and filmmakers could make this a strong TV adaptation (which there are few of).
As for the story, when you really get down to the basics of it, the whole premise of the show is completely ridiculous, and makes no logical sense. But there are some fixes to make it just a bit more plausible.
To start off, Gilligan and Roy Hinkley (The Professor) are now brothers. They live in Hawaii. Roy is obviously a professor at the university, and let’s say it’s in marine biology. Their uncle, the Skipper, runs a boat tour service, showing off the sights of the islands, and Gilligan works for him. Roy wants to show one of his benefactors (Thurston Howell) the work he’s doing with a unique research project, so he asks his Uncle to take them out to sea. Howell is wealthy business man and also sits on the board of directors of the University. Roy brings his girlfriend/research assistant Mary Ann. Howell brings his wife, Lovey, and niece, Ginger, who’s an actress, thinking it’s just going to be a quick trip, and a fun way to see the ocean. Then the storm happens, they get blown off course, they crash on an island, guidance and comm systems aren’t working, so they now have to figure out a way home.
Gilligan –
A few names sprang to mind when coming up with the right guy to play Gilligan. In this era, he does have to be good-looking, but there needs to be a nerdy quality to him. Something earnest, sweet, naive, and very funny. Again, slap stick just won’t work anymore. Jason Segal was the first name, and he’s done well with I Love You Man, Forgetting Sarah Marshall and How I Met Your Mother, but there’s just something about him. He’s just a big guy. A big, oafish kinda guy, but still with all those aforementioned qualities. Yes he’d be good, but there’s one small screen actor who would be great- Chuck‘s Zachary Levi. Levi’s got an endearing quality about him, you can’t help but like the guy. He’s relatable, unsure of himself, slightly awkward, but still affable. I think Zach Levi be the perfect Gilligan.
Skipper –
When picking the right actor to play the Skipper, I wanted to take into account the tonal shift the story and spirit would have to take to appeal to modern audiences. The bumbling, pudgy, middle-age guy just wouldn’t cut it. I thought of a few guys who could do it, and for a while, the strongest candidate was Kevin Kline. But then I was watching Out of Sight and Michael Keaton caught my eye. I started thinking back on his career, the characters he’s played, the things he’s done, and I knew that Keaton is the perfect choice for the Skipper Jonas Grumby.
Thurston Howell III & Lovey Wentworth Howell–
This was another role that I spent a lot of time thinking about. But most of that was how to cast it. Each role individually, or together as a couple? How old or young did I want to go? Of course they’d still be the elder of the castaways, but did I want to go late 40’s or pushing 70? What’s the age range? But what it eventually came down to is a chemistry between the two characters, and the ability to be funny as well. And when I took into account certain creative liberties they may (and I think should) take, there were only two people I wanted for the roles of the Howells, a great Hollywood couple in their own right, William H. Macy & Felicity Huffman. Their interaction in the video comes at the 3:45 mark.
Ginger Grant –
For Ginger Grant, you need that classic bombshell look, but not a party girl socialite that dominate the headlines of today. The character was a legitimate actress in her time, and to play the character any other way, would be a disservice. Two actresses could and should do it, for all the right reasons. Mad Men‘s Christina Hendricks or Quantum of Solace and Prince of Persia star Gemma Arterton. Now I of course am basing my casting choices around potential story alterations that I will go into after the casting choices, but as of right now, based on my choices… Gemma Arterton. Hendricks is just a tad too old. In the video, she’s the one with the short, black hair.
The Professor –
This was perhaps the most difficult role to cast. He had to be a handsome actor, yet still believably academic. He had to be close in age to Gilligan, Ginger and Mary Anne, who are skewing younger, but not too close, I did want an air of maturity about him. I started out with an idea of David Duchovney, but he’s just too old at this point, I was basing that decision on him 10-15 years ago. But I had a starting point. And because of the story alterations I’ve come up with, I’m going with John Hamm. He’s only 6 years older than Levi, so they could conceivably play brothers.
Mary Ann –
For Mary Ann, I needed an actress with the perfect amount of “girl next door” appeal, and to be about the same age as John Hamm. There was one name, and one name only that sprang to mind for this one: Elizabeth Banks.
The Empty Theatre 
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