O.O Tropico YAAAAY
Tropico 1 was SO much fun. You could abuse the hell out of your people but you'd end up with horrific rebellions and rampant starvation if you pushed them as hard as you could. The only way to play it without any military bases was full-out democracy with free and open elections that you rarely ever cheated very much in. If you started oppressing them, it was a very slippery slope that I never kept my footing on...
My only real problems with the game were with labor management. If you think DF is annoying... You had no control over where people lived, so sometimes they would take a laboring job over in city A, then move their home to city F, so whenever they went to work they would walk aaaalll the way to City A, then to the work site, swing their hammer literally exactly one time, then clock out--and still get paid as much. Also, you thought DF was bad when you need those beds made now but your carpenter is on permabreak? Sometimes all of your dock workers would be off eating, at church, etc., with no sense of sane work schedules, which means that sometimes you just couldn't get any money for months because nobody would show up to export your goods.
Aside from that, the game was a serious blast. Tropico 2 was weird but fun, not worth the buy though.
I saw in a Tropico postmortem that their team couldn't make up their mind between a brutal dark realistic sim, a comedy, or what. And you can see it in the person art. Some are very cartoony and some are far more realistic.
If you thought SimIsle was a great idea but its execution was pants, Tropico has -better- execution at least.