Tony Montana – Scarface
Anyone who used the F-word that often has to be on this list.
Sonny Corleone – The Godfather
He may have died but you just don’t get much cooler than Sonny. Devoted to his family and will take down anyone who even remotely threatens them. Highly tempered but great with the ladies.
Han – Enter the Dragon
Han built up quite a little gang there in his private island. If it weren’t for Bruce Lee coming in and busting his ass he’d probably still be running his dope operation overseas.
Junior – Kiss of Death
He may have had asthma but he made a guy strip and bench pressed a chick 40 times.
The Joker – Either Batman
Certainly a different kind of gangster and perhaps the scariest, the Joker isn’t on any side. He just is.