Machine Gun Kelly. Probably one of the cooler nicknames out there. Love the fedora and the raised eyebrow.
The Purple Gang from Detroit. While I was a big fan of Capone's southside outfit, the Purple Gang will always have a spot in my heart. I know for a fact that all guys wish they looked this cool when someone takes a picture of their crew.
I'd be remiss if I didn't throw Mr. Dillinger up there. Public enemy no. 1 certainly takes a hard mugshot, no?
Remember, a gangster is only as good as his gun and his hat. Check out Max's piece on Optimo hats and get yourself a real hat.