How to tell Bruce Springsteen bad news

DEADLINE: What parallels were there between Silvio and Miami Steve? You can see the affection between you and Springsteen onstage, and in the stories Bruce tells between songs about the old days.

VAN ZANDT: The common dynamic is, as a best friend you have an obligation to tell the truth and you’ve got to know when to do that and how to do that, and it’s never going to be easy when it’s bad news. But once in a while, hopefully rarely, but once in a while you’ve got to be the one to bring the bad news because nobody else is going to do it, so you’re obligated. That’s your responsibility as a best friend. Sometimes they will get mad at you and then, as happened on the show, you see occasionally Jimmy will be screaming at me over something and that’s how it is in real life.

It’s just one of those things that goes with that job, that relationship, in being the only one who’s not afraid of the boss because you grew up together and that puts you in a special category that is very, very useful and very helpful to that boss whether they like it or not. No boss likes to hear bad news or hear they made a mistake. You can’t do it every day or even that often, but when it’s really, really important, you pick your moment and you’ve got to take the consequences and you just have to live with that. That’s the job. And ironically, right after we filmed, Bruce decides to put the band back together that same year.

from this Deadline oral history of The Sopranos.