Despite it being a show about warring and scheming mobsters, The Sopranos is packed with light-hearted moments. Capos Paulie and Ralph enjoy cracking jokes at the expense of others while Tony always makes an effort to dilute the seriousness of any situation. However, there have been some pretty sad moments.
The devastating moments have in turn led to some sad remarks from the main characters. Such remarks have been influenced by various factors, including betrayal, heartbreak, death, regret, and despair. The sad words have also helped emphasize the fact that life is never easy, especially when you have ties to the mob.
When Big Pussy Realizes He Is About To Be Shot For Being A Traitor
"Not On The Face, Okay?"
Big Pussy is undoubtedly one of the best FBI informants on The Sopranos but his run comes to an end when a paranoid Tony discovers recording devices in his bathroom. Tony, Paulie, and Silvio trick him into going on a boat ride where they finally let him know what's about to happen. Accepting his fate, he requests to not be shot in the face.
Big Pussy's no-bullet-on-the-face request is tied to the fact that he wants people to at least view his body during his funeral. Like weddings, funerals are shown to have much significance in the mob. The turncoat is indeed granted his request to not be shot in the face but he never gets to have a funeral since the trio throws his body in the water.
When Junior Forgets He Was In The Mafia
"I Was Involved With That?"
In Tony's final scene with Junior, the mobster approaches his uncle at the retirement home and talks to him but he can't remember anything because he has advanced dementia. When Tony tries to jog his memory by reminding him of "this thing of ours"—one of the best phrases in The Sopranos used to refer to the Cosa Nostra—Junior still doesn't remember.
Unfortunately, Junior can't remember being in the mob yet he was one of the biggest players in New Jersey. Ideally, he should either be reminiscing about his glory days or feeling remorseful but fate hasn't granted him a chance to have such feelings. It's a reminder of just how much damage disease and old age can do. Even sadder is that he can't remember his nephew.
When Johnny Sack Begs The FBI At His Daughter's Wedding
"Let My Daughter Leave At Least, Come On."
Former Lupertazzi Don, Johnny Sack is granted a few hours from prison to attend his daughter's wedding. But just as his daughter is about to be driven away with her husband, the feds show up and put him in cuffs. This causes him to start sobbing.
Family means a lot to members of the Cosa Nostra and that's why Johnny Sack pulls plenty of strings to ensure he is allowed to attend his daughter's wedding. That he isn't even allowed to see her off is disheartening. Every guest can't help but sympathize with him as he sheds tears while being dragged away.
When Christopher Laments About His Miserable Life
“You Ever Feel Like Nothin’ Good Was Ever Gonna Happen To You?”
In one of Christopher's heart-t0-heart moments with Paulie, he confesses that he feels like a fictional character roaming around with no story arc. He also worries that nothing good will ever happen to him.
For most of the series, Christopher feels lost. Nothing ever works out like he thinks it will and part of that has to do with his lack of discipline. No matter how much advice he is given, he just never sets himself on a proper course. Consequently, nothing good happens to him and he eventually ends up dead.
When Carmela Confesses That She Loves Furio
"I Have Been Dreaming And Fantasizing And In Love With Furio."
Tony Soprano's list of mistresses is long and Carmela soon finds out about most of them. To spite him, he confesses that she has been in love with Furio for a long time. This leads to one of the biggest fights in the show.
The fight sees Carmela and Tony at the lowest point in their relationship. Both love each other but they've hurt each other so much that they've grown sexually attracted to other people. The fight not only leads to a separation but also causes Furio to flee back to Italy to avoid retribution.
When Dr. Melfi Reconsiders Telling Tony About The Sexual Assault
"No!"
In what is one of the worst things to ever happen on the show, Dr. Melfi is attacked and raped by an employee of a diner. During her next session with Tony, she begins sobbing, and when he asks her if there's something she'd like to tell him, she says there is none.
It's a heartbreaking moment because it's obvious that justice will be delivered immediately if Dr. Melfi just opened up about her ordeal. Movies like The Godfather have shown that making people pay is what mob bosses do best. However, the therapist reconsiders telling Tony because she knows exactly what he'll do and she can't live with herself if she knows she was indirectly irresponsible for the death of her attacker.
When Janice Forces Bobby To Forget His Dead Wife
"The Dead Have Nothing To Say To Us."
On the day that would have been the 14 marriage anniversary of him and his late wife Karen, Bobby takes a cake to her grave. This angers Janice who demands he forgets about her.
Bobby and Karen's peaceful marriage made them one of the best couples in The Sopranos. It's understandable for him to miss her and, unfortunately, Janice forces him to forget her because it's clear who the better partner for Bobby was. Janice is only attempting to erase Karen out of Bobby's mind so that she can control and manipulate him as she wishes.
When Tony Tells Dr. Melfi How He Feels About Christopher's Death
"I Haven't Been Able To Tell Anybody This. I'm F***n Relieved."
In his next therapy session after Christopher's death, Tony confesses that he is relieved that Christopher died. He argues it's because Christopher had become so much of a mess.
Tony and Christopher had been close for most of the series so the comment paints him as rather insensitive. His remarks sound even harsher because he is the one that killed Christopher yet everyone believes the death happened due to injuries sustained from the accident.
When Adriana Hints That She Can't Get Pregnant
"What If We Can't? If I Can't? Would You Still Love Me?"
Adriana once surprises Christopher with the suggestion that they should get married immediately. He argues that it would be difficult since she can't raise kids while running a nightclub. Adriana then hints that she cannot have kids.
Because she is deeply in love, Adriana is eager to do everything in her power to keep Christopher. Fertility problems are always a serious issue and she does her best to tell Christopher about her struggles the best way possible, Regrettably, Christopher doesn't react too kindly to the revelation because he desperately wants an heir.
When Bobby Imagines How Mobsters Get Killed
"You Probably Don't Even Hear It When It Happens."
As Bobby and Tony hang out at a boat towards the end of the series, they discuss mafia deaths. Bobby figures executions always come so abruptly that one never sees it coming.
The chat triggers melancholy because it's a moment of foreshadowing. A couple of episodes later, two Lupertazzi hitmen gun down Bobby as he is buying a vintage train set and shooting him. Interestingly enough, he sees and hears it when it happens because he looks right at the gunmen before he gets shot. There is some truth to his claim though since figures such as Tony Blundetto and Phil Leotardo get executed rather abruptly.