Originally Posted by LogicDeLuxe
The worst games of this kind I tried were Larry 2 and 3 by far, though.
Ugh... Larry 2... You have to make sure you buy the sunscreen before you leave for the cruise, otherwise you'll instantly die of skin cancer when you try to sunbathe. At least that one was sort of logical and semi-predictable (if you apply Sierra death-is-lurking-around-every-corner logic). The part that really got me though was having to swim to the bottom of the pool on the boat to get the bikini top for your disguise to get past the KGB agents later in the game.
(Spoiler tags just in case anyone hasn't played Larry 2 but intends to.)