Sometimes, it is like this: One major success which its originator will search to repeat for the rest of his life. Ralph Stock was responsible for Mad TV which became a deserved instant hit. Mad News' fun factor came close, but it could not receive its predecessor's business triumph. Carribean Disaster should really have been called Mad Island – instead, that is just the name of the game's location.
Mad Island is the quintessential banana republic: a tiny, insignificant country ruled by a small military junta, but really – the game is set at the height of the cold war – under the more or less direct control of either the USA or the USSR. The player takes over the role of one of the four members of government – the president, the head of the army, the head of the marine or the head of the air force – and the ultimate goal is to put enough money – taxes or foreign bribes – into one's own pocket to buy a stack of land in the Antarctic and construct an escape vehicle to go there and live well ever after; while preventing the others to do the same, of course.
In a stroke of comedic genius, the only possible candidates are always… the four members of the old government! I.e. the ministers can overthrow the president, but at the very least, this guy will become a member of the next government again. It's all going in circles, just like in real life. The other inhabitants of the island have the vote, too. So they have to be persuaded one way or another; the regular way by holding speeches, glueing posters or throwing parties or, if you are on good terms with the head of the secret police, also by less regular means…
Almost all inhabitants also have another function on the island (apart from voting repeatedly), though, not just the secret police guy. His very own brother, for example, is leading the anarchist rebels, for example. The local radio DJ plays an important role as well: For an appropriate sum, he will happily spread false rumors about the political competitors. Then, there is the cardinal who deals with, of all things, weapons and heavy military equipment. And of course the industrialist whose factory manufactures the ammunition used by these arms: popcorn.
There is an interesting balance in the gameplay, because of the different and changing roles the player and his competitors can have. The presidential post is where the money is, but on the other hand, this person does not have any actual direct power. That lies with the ministers who have the weapons at their disposal, which they can use to block roads or even attack certain buildings to make them inaccessible to their enemies. Which of course only works as long as they have some money to buy appropriate arms and supplies – which has to come from the president.
Unfortunately, the actual experience differs a bit from this. The best strategy to win involves just becoming president once, collecting as much money as possible while keeping the ministers down and then switching to a minister post once. That is all too plain, because the options the game gives are ultimately too simple to really challenge (or even just temporarily confuse) the player. It may be funny that the game requires basically no long-term strategy (ally with the secret police one day and with the rebels the next – satirical commentary on how it eventually all comes down to the same thing?), but it also implies that the player can never really do anything wrong; at worst, it will delay the inevitable success by a day or so.
Without a doubt, the freaky idea deserves praise for its total disregard of any political correctness. The gameplay ideas are there as well. Maybe it's just that this island is too small: Effectively, you will need just three or four stops every day in the game where you will repeatedly do the same things. This becomes routine very quickly. Other roles are only really useful once or twice in the whole game. There is no real room for different strategies. It all comes down to the island being too sparsely populated; some additional (useful) characters and maybe even some more links between them, i.e. actions which involve more than one person and which maybe are not quite as clearly positive or negative in their effect, would certainly have helped long-term motivation. For some quick and short fun, it is a safe recommendation anyway.