Revisited this movie last night, and it is probably my third or fourth viewing. I like a film that has a bit of ambiguity to it, which is probably the biggest contributing factor to its repeat appeal. I love the cinematography and the directorial flair that is evident in so many of the major scenes (the 'Danny Boy' sequence, the execution at Miller's Crossing scene and its revisitation, the violent climax with the death of 'the Dane'), and wonderful performances by Finney and Turturro and especially Jon Polito.
It was interesting to me on this viewing to notice all the 'bookend' scenes, the Mob boss visited by the mayor and chief of police (once for Finney and once for Polito), the execution march into the woods (once for Turturro and once for Byrne) neither of which works out as expected), the midnight visits in Byrnes sitting room (Finney and Turturro), the police raids (once for Finney and once for Polito) and probably more that I missed.. and I suppose it has something to do with the Gabriel Byrne character's duality, his playing one side off the other, and the constant reminders in the script about eithics and morals, good/bad in a world where neither side is particularly clear.
I guess the biggest ambiguity to me is in Tom's (Byrne) motivations throughout. He frequently proclaims that he is looking out for Leo (Finney) and his best interests, and you almost believe him, but then at the end you get the impression that the whole sequence of events was put in motion in order for Tom to get out from under his own bookmaker debts, which never quite rings true with me. Is it his doomed love with Leo's girlfriend (Marcia Gay Harden)? He never treats her with little more than contempt throughout. Is it true like he says just before killing Bernie (Turturro) when Bernie asks him to "look into your heart" and he replies "what heart?" (why didn't he kill him at first at Miller's Crossing? in order to set up Caspar and the Dane? is this for Leo's benefit or Toms?) -- but then we are left with a strange final scene at a lonely graveside between Leo and Tom which I have never quite understood every time I've seen this.
Anyhow, I'll probably be back again, this is one of my favorite Coen films, and be sure and check out my other favorites: Blood Simple, Barton Fink, O Brother Where Art Thou, & Fargo