Not happening now, but if it were, I dig Fox411's fantasy casting.
Gilligan - Michael Cera
Skipper - William Shatner
The Millionaire - Alan Dale
His Wife - Jessica Walter
The Movie Star - Christina Hendricks
The Professor - Simon Baker
Mary Ann - Ginnifer Goodwin
My only qualm would be Lost's Alan Dale as Thurston Howell III. He's been the heavy so many times, I wonder if he has the ham inside him. I'd like someone more like Eugene Levy or even Michael Gambon.