Just finished a rewatch. Hadn't rewatched an episode since its original run ended so it's been a while. A few thoughts.
1. It holds up! In the great The Wire vs. The Sopranos debate I've always been a Wire guy. Still am. BUT it's a closer argument than I was giving it credit for past times I've been in those conversations. The things I held against The Sopranos (mostly how it felt like it really spun its wheels at times) didn't bother me nearly as much. Probably due a little to watching it in chunks of episodes now versus the ol' wait every week method.
2. Another TV comparison. Tony and Walter White are often lumped together as bad guys who've been misinterpreted by fans who think they're cool. But unlike Walter and Breaking Bad, the writers on The Sopranos always have Tony in a pretty dark light. There are times you like him and sympathize with him but they never let it get too out of hand. He's a bad, damaged man. Not an anti-hero. That's versus Breaking Bad where sure Walt is mean to his wife, but he's also a supervillain who sets cool traps to kill cartel leaders and neo-Nazis and gets a tidy redemption arc in the end. (I like Breaking Bad, but the creative team there is super disingenuous when they try to tell folks to not like/enjoy Walt). I don't think The Sopranos deserves any criticism on that front.
3. It's a given that Gandolfini and Falco are all timers. Bracco, Imperioli and Chianese are good too. But the two performers who really POPPED for me on rewatch were Drea di Mateo and Aida Turturro. Adrianna starts as a kinda nothing character and becomes maybe the most sympathetic character in the series, largely due to the performance. Janice is pretty detestable from day one as a character but man does Turturro absolutely bring it.
4. I appreciate the role dreams play in the show. But man the depictions are a lot of super literal, corny bullshit. They have this sheen of faux-surrealness but then someone says something or something happens that is very literal to what's happening at the moment. It's hacky writing for a show that's often better. It's David Lynch for dummies.
5. Two of the more irritating running subplots at points in the seires -- Vito, whatever AJ's bullshit of the moment was -- didn't bother me as much. I wouldn't say either are any more compelling, but I appreciated them more as examples of collateral damage of the life. Add examples to deepen the story.
6. Paulie Walnuts is and will always be comedy gold.