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1. Chicago smile
When someone has their throat cut from ear to ear, it is known as a Chicago smile.
He squealed. The mob gave him a Chicago smile.
2. Chicago smile
A violent act where the victim is placed with their mouth across the edge of a curb and a person stomps until the edge of the mouth is torn apart, thus creating a smile.
That buster sold me bad weed, so I gave him a Chicago Smile.
by Headman Jun 22, 2005 add a video
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