Tropico
Every time I play that game I do the same thing:
Get elected as a Capitalist.
Start growing Tobacco.
Kiss up to the USA.
Build a couple of Cigar factories, get insanely rich.
Have a huge Housing and Labor shortage.
Allow America to build a Military Base on my island because I am a whore.
Build a few High Class hotels.
Go from having to pay educated foreigners to come work in my island to building stuff I don't really need just so I can give the College educated people something to do.
Have the Intellectuals get bored with me and start voting for my rivals despite my government being always as democratic as possible.
Save Game. Send the Army on a killing spree against the Environmentalists just to see if I can fully erradicate a faction. Get bored, load previous game.
Win as many elections as I can due to the support of the Capitalists (wait a second, I thought everything was State-owned in this game?).
Eventually lose an election by a narrow margin. Despite having ruled the island democratically for 120 years and turning it into a highly developed nation, end up in a rowboat with all my belongings.