1. Jacked Stiff = Basically Killed, Dead, Finito. If someone Jacks you stiff, your dead (or beat up really bad.)
2. "Jack Stiff" can also be used as a name for someone who is living such a reckless lifestyle that they will soon be dead.
3. Jack you stiff = can be a threat.
eg. 1. ..Dumb-ass was running with the Bulls in Pamplona and got Jacked Stiff.
eg. 2. Mikey: you heard about that fool that messed with Tiny?
Tommy: Yeah, that motherfucker got Jacked Stiff!
eg. 3. This is your last chance, you mess up this time and I'll Jack you stiff!
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