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I really don't understand what the Wicked Game achievement does.

Achievements unlock accessories that give pretty big, somewhat game-breaking boosts. Wicked Game gives you the gold bracelet which doubles cash earned from working.

how do you unlock the achievement?

All of the achievements are:

Wicked Game - earn a total of $2000 

Love The Hardest Way - have sex at least 50 times

When Love and Death Embrace - get both High and Drunk meters to 99% without blacking out and go to sleep