"Gilligan's Island" was the epitome of wholesome family fare during its 1964-1967 run. This band of randoms managed to (mostly) keep their cool while being stuck on a desert island with nothing to eat but coconut cream pies and zilch to do but try to fix that darn boat. At least ... that's what the creators would have you believe!
Fan theories about this classic show have abounded since far before the "Interweb" was available to spread them. Why would a wealthy man carrying a ton of cash bother taking a "three-hour tour" on a small boat manned by a skipper with a bumbling sidekick? What was a movie star doing there, with all her feather boas and evening gowns packed for such a short trip? For that matter, why did everyone seem to have so many extraneous clothes and supplies for an excursion that should have had them home by lunchtime?
Either we're being too nitpicky, or the obvious explanation is that millionaire Mr. Howell was on a waterway drug deal, and had the good sense to load up enough cargo just in case an aqua-bust occurred and a getaway boat chase became necessary. He paid off Gilligan to ferry him. The Skipper, too. You can't help but feel bad for Mary Ann in this situation, since theorists peg her as an undercover federal agent aboard to witness/manage the criminals [source: Bailey].