OH! OH! We’ve all been missing the most obvious one!
The Professor : Jim Parsons from “The Big Bang Theory”.
Absolutely.
Kelsey Grammer as Mr. Howell
Kathy Griffin as Mrs. Howell
Miley Cyrus as Mary Ann
Jim Carrey as the crazy stranded stereotypical Japanese soldier who doesn’t know the war is over even though it ended 20 years before he was born.
DJ Qualls as Gilligan
(I’ve seen Michael Cera’s performance already- kinda sweet but kinda cute nerdy kid— yep, seen it- this would add a sailor hat, that’s about all.)
Psst, post #18.
Came in here to mention that.
Plus I just can’t get me enough Zooey.
For the rest:
Gilligan - Michael Cera would be good. I think that Jay Baruchel (“Danger” from Million Dollar Baby) would do well, too.
The Skipper too: A second for John Goodman
The Millionaire: Michael Caine
and his Wife: Betty White YESS!! a second, third, or fourth.
The Movie Star: Nicole Kidmann - for some reason I think that she could nail it. If not, Christina Hendricks
The Professor: David Tennant
I don’t think there are enough antibiotics in the world to cure this island. It’s like a leper colony, only with STDs and heroin.
You know I’d actually PAY to see this cast 
Possibly the only time in history two people have independently thought of D.J. Qualls within the same 24 hour period.
At one time there was talk of a GI movie with Brian Dennehy as Skipper and Julia Louis-Dreyfuss as Mary Ann (now a NYC single woman instead of Kansas farm girl). It was soon after Seinfeld premiered but before it was the biggest show on TV. Apparently the producers sobered. I just don’t think there’s enough nostalgia for the series for it to be a hit unless they add lots of broad comedy and maybe a naked Zac Efron as Gilligan.
Though if they do make it Dawn Wells should play Lovey Howell. She’s not much older than Natalie Shafer was when she first played the role and is in fact several years younger than Natalie Shafer was when she last played the role. Tina Louise would only be involved if she was to star in the movie and judging from the last time I saw him Russell Johnson is too old and feeble to do anything more than a very brief cameo.
I actually do recommend the TV movie Surviving Gilligan’s Island (available from Netflix). For those unfamiliar it was a TV docudrama starring Bob Denver, Dawn Wells, Russell Johnson and Sherwood Schwarz as themselves and with other actors playing all 7 castaways, Schwarz and others in vignettes about filming the show and it’s an exceptionally charming movie. It touches on the cast’s dislike of Tina Louise (though it does have a couple of funny stories that portray her in a more playful light), the beloved eccentricity of Natalie Schafer (and even a poignant moment involving her lack of a sex life- yes, really), the assassination of JFK (which occurred while they were shooting the pilot) and other anecdotes.
One of my favorite moments is when Shafer is bonding with Wells in the flashbacks and Wells is bold enough to ask her age, which Shafer did not reveal to anybody. Shafer tells Wells that “my husband always asked me my age- I told him I would never ask him who he was sleeping with if he didn’t ask my age- when he was dying I went to see him” [they were divorced by then] “and he said ‘Natalie, before I go, just whisper in your ear how old you are’. So I bent down, placed my mouth to his ear, and said ‘Never’.”
[ul][li]Demetri Martin as Gilligan[/li][li]Dan Aykroyd as the Skipper (Check him out as Jimmy Carter in Funny Or Die’s Presidential Reunion and you’ll see what I mean)[/li][li] Alec Baldwin as Mr. Howell[/li][li] Meryl Streep as Mrs. Howell[/li][li] Nicole Kidman as Ginger[/li][li] Carey Mulliganas Mary Ann (if she can do a credible American accent)[/li][*] Jeff Goldblum as the Professor (I can’t beat that casting choice)[/ul]
The Skipper too: Seth Rogen
The Millionaire:** Mike Myers **<–You HAVE to have an SNL alum to make a good comedy
and his Wife: Madonna
The Movie Star: Sofia Vergara
The Professor: **Richard Dean Anderson **
and Mary Ann: **Drew Barrymore **
Lots of inside jokes about the star’s other films and tv series.
My cast guarantees BOX OFFICE GOLLLLLLLLLLLLLLLLLLLLLLLD!
Of course, you could have ***this ***cast (which is why the Minnow sunk in the first place):
The Skipper too: Bruce Bruce
The Millionaire: Reginald VelJohson
and his Wife: Aretha Franklin
The Movie Star: Mo’ Nique
The Professor: Cedric the Entertainer
and Mary Ann: Gabourey Sidibe