Agree about the music. It was okay, but it could have been better. Personally, I like Van Morrison’s Astral Weeks but (1) It wasn’t a hit in its time; and (2) Do I think there’s any chance in hell that it was a cult favorite among Jersey mobsters? No.
I was a big fan of the TV show, but this movie was just okay. As you say, it tried to do too much. The acting was good, especially Nivola, Liotta, young Gandolfini, the Italian actress playing Dickie’s stepmother/mistress. But they were working on a rather ho-bum storyline that never really enthralled me. Also, the portrayals of Silvio and Junior seemed to drift into parody of the TV characters.
I agree -- the Silvio character particularly made it a caricature.
What I really missed was the humor, dark though it was in the TV show. The original premise was absurd--that a mob boss would have panic attacks and go to a therapist. There were frequent surreal episodes like the talking fish on ice in a fish market mocking Tony after Pussy's murder, and then his daughter giving him a battery-powered talking fish novelty placque for Christmas. It was Fellini-esque.
This movie could have used some of that surreal "shorthand" symbolism, since it was supposedly the clairvoyant knowledge of the narrator, Christopher, who was already dead. Instead was very grim and humorless. It cried out for quick, clearly narrated explanations, like a "wham!" camera noise and a still snapshot of young Tony with his pals Artie, Pussy and Silvio as children in their confirmation class, as the voice tells you who they are—then on to the next scene. As it was, you had to try to glean who was who from which boys were using the f-bomb every other word as they walked along the street in profile.
I thought the use of Ray Liotta as a sort of morality guru was interesting. He suspected more than he was saying about Dickie's version of events that killed his father and his goomar.