The Sopranos was best known as a gritty mob drama featuring inimitable performances, shocking character betrayals, gobs of violence, intensely trippy dream sequences, and quotable one-liners out the wazoo. As brutal and merciless as most of the characters were, though, there were also some truly sad moments.

Fans of the decorated HBO crime drama have been debating which moment from its six seasons was the most gutwrenching of them all over on the Reddit fan page, and there are a lot of quality contenders on the list. Tony Soprano (James Gandolfini) might’ve considered “remember when” to be “the lowest form of conversation,” but that’s certainly not the case here.

Originally published on tvinsider.com, part of the BLOX Digital Content Exchange.