The course of evil
Brilliant piece, John. Anti-heroes are all the rage these days. The really good ones are written to inspire the sort of reflection you offered about Tony Soprano.
We're not likely to return to the days of movie commissions decreeing that crime can never, ever be depicted as glamorous or successful. One problem with such an approach is that it keeps us from understanding how a sympathetic character could fall from grace and pursue a life of crime. The crooks all have to be clown dolls with their switches flipped to "evil," like DeNiro's Al Capone.
My favorite gangster character of the moment is Walter White, from the superb "Breaking Bad." The course of the show has followed his descent into becoming a Tony Soprano sort of mob boss. He's still sympathetic, or at least easy to relate to, in many ways. He still has personal problems we can understand; sometimes we get a glimpse of the guy we began with, at the start of the series. But he's running a drug empire now, and he's discovered the ruthless tactics of the gangster have a certain inexorable logic to them. He accepted a monstrous crime against an innocent child that would have sent his old self screaming into the streets, because after a few months of running a criminal empire, it made sense - a regrettable necessity, rather than a soul-shattering horror.
What got Walter White started down this terrible road? More than anything else, he decided the world - fate, God, society, everyone, everything - had been unfair to him. He snapped and decided he'd start being unfair in return. But he was only going to cheat a little! He's a chemist by trade, and he thought he could mix a bit of criminality into an otherwise decent life, the way volatile ingredients can be mixed into a useful formula. He thought he was dying, and he just wanted to provide for his family. He was terrified when he discovered what his criminal partners were capable of. Then he found out what he was capable of, and now he is The One Who Knocks.
There are a lot of ways a good man can go bad. Bad men can find it very difficult to pull out of the downward spiral. Conclusion: don't go bad, not even a little. It's not an easy path to walk, but the course of evil proves infinitely harder on your soul.