I've never met a real gangster, fortunately, but some of my favourite movies involve them. I love those 1930s Warner Brothers productions with James Cagney and Edward G. Robinson and Humphrey Bogart wearing fedoras and acting tough. In more recent years, I've loved the Godfather movies, Goodfellas, Miller's Crossing and Donnie Brasco. I also like the TV show The Sopranos--though the first season was the best--and parts of Boardwalk Empire.
As far as real-life gangsters go, I think we should legalize and regulate drugs and the sex trade to get rid of the violent racketeers. But most North Americans haven't learned their lesson from the failure of Prohibition.
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