The Sopranos isn't often regarded as an emotional series. It never really veers into maudlin territory, and even when it depicts dramatic material, it does so with a rather cold and detached demeanor. Deaths are depicted as just another aspect of mafia life, and therefore, aren't often portrayed in an overly emotional manner. Whereas other shows utilize sentimental music or other mawkish filmmaking techniques to depict emotion, the dramatic events of The Sopranos are typically depicted with an objective and impersonal eye.
However, there are still numerous heartbreaking moments to be found throughout the story, whether it be from a character's death, a quote, or a hard-hitting bit of character drama.
When Tony Saves AJ
According to Reddit user NotAlaskan, "Tony holding AJ after saving him from drowning" was the most heartbreaking moment of the entire series (that, and Bobby being killed in the penultimate episode). AJ had one of the best character arcs on The Sopranos, which showed him sinking further and further into nihilism before he finally attempted to end his own life in the Soprano family pool.
The scene in which Tony saves his son is filled with emotion, complete with both characters crying and Tony calling AJ his "baby." It's some of the most difficult subject matter that the show would ever depict, and unlike many scenes involving AJ, it's shot in a very tender and sympathetic manner.
When Tony Kills Christopher
Despite being one of the most shocking deaths in the series, Tony's killing of Christopher is nevertheless depicted with little emotional flair. There is no musical accompaniment, and no one cries or begs for their lives.
Tony simply plugs Christopher's nose and watches him die in silence, and a barely conscious Christopher slowly passes from the lack of oxygen. Despite the lack of drama, the scenario itself is incredibly effective, and Reddit user wobbly_au considers it the saddest moment of the series, writing, "Personally, I find when tony kills Christopher was the saddest."
"Join The Club"
The second episode of the sixth season, "Join the Club" is the first official coma episode. The previous episode ends with Junior shooting Tony in the stomach, and "Join the Club" is devoted to his family's reaction to the situation. Unfortunately, it makes for quite harrowing, and unfortunately realistic, viewing.
As user UniversalPolymath writes, "Join the Club hung over my head the entire week after it first aired ... Carmela pleading with Tony to say her name when he briefly regained consciousness - followed by her breakdown in the hall after asking the doctor if 'he knows that he's dying' - just eviscerated me."
Tony & Junior In The Home
Tony and Junior shared a very difficult and complex relationship, but despite their numerous grievances, Tony was sad to see his uncle in such a state towards the end of his life. Tony visits Junior in the finale and is shocked to find him in the deep throes of dementia.
As Calikola writes, "The Junior and Tony scene in the finale absolutely slaughters me ... for the first time, Tony realizes that Junior wasn't faking his dementia. He has spent all this time and energy hating Junior, not realizing that Junior wasn't in his right mind for some time now."
Bobby's Death
Of all the unnecessary kills in The Sopranos, Bobby's demise hits fans particularly hard. Perhaps it's because he was such a childish and innocent character in a world full of cold and violent individuals.
But there's another aspect to his death that is subtly upsetting. As one Redditor writes, "Bobby’s final thought before getting killed was how his kids don’t give a s*** about his hobby." It's a hard pill to swallow, especially when people reflect on how they may have treated their parents as heartless teenagers.
When Tony Hears Meadow's Voice
One of the last things that Tony hears in his coma is the voice of Meadow pleading him to hold on. This is the saddest moment for thebarryconvex, who writes, "I find everything with Kevin Finnerty to be really devastating and it's always been my favorite section of episodes in the series."
It's undeniably a great moment, especially for those who have loving daughters. Family drama will always hit the hardest owing to its grounded relatability, and in this case, nothing hits harder than the voice of a grieving daughter.
When Tony Asks Junior, "Don't You Love Me?"
One of the greatest episode endings in The Sopranos can be found in season five's "Where's Johnny?" Upset with Junior's recent behavior towards him, Tony awkwardly sits with his uncle on the couch before tenderly asking, "Don't you love me?" It's a very rare moment of vulnerability for Tony, and its rarity further aids its emotional impact.
It's a crushing line, made all the more heartbreaking owing to Junior's silent yet teary-eyed reaction. It's no surprise that Joey12gauge finds it tragic, saying that "When Tony asks his slowly fading Uncle June 'Don't you love me?'" it is the saddest moment in the series.
Adriana's Dream
"Long Term Parking" throws viewers a bit of a curveball. Adriana imagines herself driving away from New Jersey, escaping the life of crime and her obligations within it. However, the scene then smash cuts to her inside Silvio's car, on her way to be assassinated.
It's a brilliant and heart-wrenching misdirection from the show, offering viewers a brief glimmer of hope before shattering their (and Adriana's) idyllic vision. Many people find this scene distressing, given the number of upvotes on AreYouDecent's comment that "When Adriana is imagining herself driving away and it cuts to her sitting beside Silvio," it's the series' saddest moment.
When Paulie Sits Alone
The ending of The Sopranos is dark, empty, and dreary and a great counterpoint to the bright and bustling beginning. Even the people who survive (like Paulie) are left physically and mentally alone. This is hauntingly portrayed in Paulie's final scene, which sees him sitting in front of Satriale's all by himself.
As Reddit user brosefstallin writes, "Once a bustling storefront with mob guys hanging out, eating, laughing, now reduced to a lonely and desperate man sitting at the end of an era."
When Chris Cries While Driving Home
Season five's "Cold Cuts" contains one of Christopher's greatest and most sympathetic moments. Both Tonys (Soprano and Blundetto) make fun of Chris while up north, prompting him to drive home early and alone. He cries on the way home, viciously hurt by their words and actions.
It's one of the rare moments in which viewers are allowed sympathy for Christopher, and it hits especially hard, owing to the realistic nature of the bullying. As PeteLeo writes, "Something about Christopher alone in his car driving back and crying really hit me. He’s a sensitive guy underneath it all that just wants to be loved by his cousins. Even with being a gangster and murdering people, he’s still just a kid that wants to fit in."