penitentiary crew

I want a cartoon drawing of a big muscle-built prisoner/ inmate to be the face and symbol for a possible t-shirt line. I want him to be grumpy looking but intimidating. and funny. I am including some pics.as example. I want to include the pin stripes and ball and chain. I will want this guy in different type scenarios to set the image for each different topic.
Example Our guy big muscle guy sitting on a prison cell bed with his arm around another skinny prison inmate over exaggerated squeezing him closely and the skinny guy looks real scared. The caption for this shirt "Besties for the Stay"