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Way of the Dragon (do a prison takeover with nunchuks)
Grey Matters (reach 100 intellect)
Let's Get Physical (reach 100 speed and strength)
The Monopoly Guy (reach $1000)
Butter Fingers (it's a secret...)
You don't really need to get the achievements (maybe you even have them already), you just need to do the things need to get the achievements :P
This means that you need to have 1K dollars, reach 100 in all stats, drop the soap in the shower during the shower block, make nunchuks and escape the prison using the prison takeover method.
You can choose the prison that you want to escape, but I recommend Center Perks because the guards are weak.
2: Run around naked for the whole time you play a prison.
2. Might do that one
I left it in my other pants- Escape The Jungle without a Uniform on.
Pants Pants Tazer Revolution- Escape HMP without any clothes on the entire time.
Clean Jeans- Escape Stag Flucht with 0$ on you
We need out shiv for your shank- Take everybodys combs and turn them into shivs
I'm a doctor!- Beat Center perks with Bleached Clothes, and carry with you a Medikit, Bottle of Medicine, and Bottle of Sleeping pills.