“Remember When,” much like the series as a whole, deals with people who are past their prime, and the generational conflict between emulating and denigrating one's elders. It’s an intense hour, with a lot of strong material, but it’s also a weaker episode than the two that opened the season. But, I don’t think there’s ever been a bad Sopranos episode, and the only frustrating thing about this one is that it means we’ve got to wait a week to see the next one.
I’ve been re-watching the first half of the season on DVD, and I think a large part of what gave it its bad reputation is the fact that it was just so frustrating to have to wait a week between episodes. Watched all in a row, they flow really well, and quite a lot happens. But, particularly with the season finale, I think people just needed more to carry them over the year hiatus. The season, particularly the second half, was a lot tighter than I remembered it, and stands with anything else the series has produced.
As for this episode, much like “Soprano Home Movies,” it begins with something from the past coming back to haunt Tony, in this case, his first kill. The shadow of past events has hung heavy over this entire season, each episode featuring an obsessive rehashing of past traumas that the characters just won’t let go. Ever since the first episode, Tony has talked about how he got into something that was on the way down, and more than ever, the glamour of mob life is disappearing. Tony’s major concern about Paulie is that he doesn’t have a legitimate source of income; would Johnny Boy Soprano have thought about that? Maybe, but Tony would have never seen that side. All that’s left to him is the cool guy standing in front of a cool car.
The series’ initial hook was that Tony was just like you — he had a wife, kids, suburban house, only he was in the mob. With this season in particular, we’ve seen the mob as just like any other business, struggling with corporate expansion, and reduced to increasingly pathetic jobs, like stealing plumbing fixtures in this episode. They’re putting in so many hours, are they getting something they wouldn’t get from working regular jobs? I think part of it is that they’re all addicted to the danger. When Tony and Christopher stole the wine back in “The Ride,” it wasn’t for money, it was because they were bored. In theory, couldn’t Tony legitimately buy plumbing fixtures and resell them?