16 Most Heartbreaking Moments From The Sopranos

The Sopranos was a critically and commercially acclaimed series that aired on HBO. It’s considered one of the greatest TV shows ever created. David Chase created the series and it aired from January 1

The Sopranos was a critically and commercially acclaimed series that aired on HBO. It’s considered one of the greatest TV shows ever created. David Chase created the series and it aired from January 10, 1999 to June 10, 2007, for six seasons. The plot revolved around New Jersey crime boss, Tony Soprano, as he struggles to find balance between his family life and crime life. He begins to see a therapist because he starts to suffer from clinical depression, intense anxiety and panic attacks. The series was universally praised for its incredible writing, outstanding cast and phenomenal directing. The Sopranos has won several awards for its work, including five Golden Globe Awards and 21 Prime Time Emmy Awards. Prior to the series a majority of the cast were largely unknown but have all gone on to have successful careers.

The series starred an outstanding ensemble cast, which included James Gandoflini, Edie Falco, Lorraine Bracco, Michael Imperioli, Dominic Chianese, Steven Van Zandt, Robert Iler, Jamie-Lynn Sigler, Tony Sirico and Drea de Matteo. However, the series also garnered a considerable amount of controversy for its sexuality, profanity and extreme violence. Regardless, the series has had a major impact on television. Several TV series with complex, dark and deeply flawed characters were created, such as Weeds, Breaking Bad and Sons of Anarchy, partially because of The Sopranos.

The Sopranos had many memorable moments throughout its run. The series featured romance, violence and even some humor. The Sopranos also made us cry on several occasions. It sometimes featured some of the saddest and most heartbreaking moments on TV. Here is a look at 16 of the most heartbreaking moments from The Sopranos.

16 The Death Of Johnny Sack

Johnny “Sack” Sacrimoni (Vince Curatola) was the underboss and later boss of the New York Crime Family. He was ruthless, conniving and difficult to work with. He was friends with Tony but was very much a rival at times as well. In season 5 he is arrested and sent to jail. He misses his family while in jail but hopes to get out at some point so he can spend the rest of his life with them. He does get to attend his daughter's wedding and breaks down and cries when he has to return to jail. He actually loses the respect from his friends. While in prison, Johnny quits smoking and gets in the best shape of his life. However, the years of chain smoking caught up to him and he is diagnosed with cancer. The season 6 episode “Stage 5”, is the final appearance of Johnny Sack. The once powerful and feared gangster slowly dies in the prison hospital with his family by his side.

15 The Unspoken Love Of Carmella And Furio

Carmella Soprano was a simple housewife of a gangster and mother to his children. However, she wanted more from her life and desired to have love and attention. Her husband, Tony Soprano, rarely gave her love and attention. He usually expressed it by buying her extravagant jewelry and gifts. Furio Giunta (Federico Castelluccio) gave her the attention she was seeking.

Carmella and Furio were deeply in love with each other but never acted on their feelings in any way. Furio worked as both Tony’s driver and bodyguard. The most exciting moment of Carmella’s day was opening the door and seeing Furio. The worse moment was when Tony would come down. They knew they could never be together and they never expressed their feelings. Furio realized things were getting too intense, so he suddenly left one day. Later, during a fight Tony finds out about Carmella and Furio’s feelings. He is enraged and promises to find Furio and kill him. Furio is never seen again and Carmella moves on with her life.

14 The Death Of Pie-O-My

Tony Soprano had witnessed/participated in the deaths of his best friends, had his heart broken and his marriage nearly ended. However, nothing could make him break down and sob like the death of an animal. For example, his panic attacks start to intensify when ducks living in his pool leave. Later in season 4, Ralph Cifaretto (Joe Pantoliano) purchases a racehorse, Pie-O-My. Tony quickly falls in love with Pie-O-My and acts like she is his horse. Tony and Ralph never got along but the situation got worse when Ralph killed a stripper, Tracee, in the season 3 episode, “University”. Tony and Ralph briefly get along after working their problems out. However, Ralph is unhappy when Tony expects a cut of Pie-O-My’s winnings. In the season 4 episode, “Whoever did this”, Ralph’s son is accidentally shot with an arrow and ends up in ICU. Ralph’s devastated and upset the rest of the episode. He even seeks advice from the priest, Father Intintola.

Later, Pie-O-My’s stable burns down and kills Pie-O-My in the process. Tony is devastated and hurt over his pet’s death. So much so that he visits Ralph and soon suspects that Ralph was behind the fire. A violent fight ensues which results in Ralph's death. Tony didn’t cry for Ralph, but Pie-O-My’s death is something that stayed with Tony forever.

13 Tony’s Coma

via:The AV Club

In the season 6 episode, “Members Only”, Uncle Junior shoots Tony and he ends up in a coma. The series depicts the events in Tony’s coma, which seem to indicate he’s on the verge of death. In the coma, Tony is a salesman that is caught up in a case of mistaken identity. He struggles to figure things out in the coma. For his family, the reality of his potential death is all too real. The family struggles to keep things together. Carmella is constantly in tears, Meadow won’t leave her father’s side and AJ struggles with his complex feelings.

The heartbreaking moment occurs when the doctor tells Carmella that it doesn’t look good for Tony and she breaks down into tears. Christopher consoles her as she sobs. Later, in Tony’s coma he is about to enter a house, which implies that he’ll finally crossover and die. However, he can hear the voice of a young girl calling out to him. He wakes up from the coma to reveal it was Meadow calling out to him.

12 Dr. Melfi Rejects Tony

Tony Soprano was used to getting his way and whatever he wanted. He would do this through intimidation, manipulation and violence. He constantly cheated on his wife with anything with a pulse. He begins to see a therapist, Dr. Jennifer Melfi (Lorraine Bracco), after suffering from a series of panic attacks. He is reluctant to see a therapist but soon starts to fall in love with Dr. Melfi.

In the season 1 episode, “Pax Soprano”, he expresses his love for her but she rejects him telling him his feelings are simply a by-product of the therapy. As the years go by his feelings for her grow and he quits therapy at the end of season 4. In the season 5 episode, “Two Tonys”, he does everything he can think of to make her fall in love with him. He sends her flowers, asks her out for dinner and buys her cruise tickets. Melfi turns him down each time. At one point he aggressively grabs her and kisses her. She rejects him and tells him this is more about his desire to resume therapy. She also tells him that she can’t be with somebody who cheats, lies and is shellfish. Tony can’t handle this rejection and storms off. His heart is broken over the rejection but later returns to therapy. In the season 6 episode, “The Blue Comet”, Dr. Melfi officially ends the therapy with Tony despite his protest.

11 Tony And Carmella Separate

With each season finale of The Sopranos, fans would ask the same questions: who is getting whacked this year? However, the season 4 episode, “Whitecaps”, saw a relationship get whacked instead of a character. On the surface, Tony (James Gandolfini) and Carmella (Edie Falco) were deeply in love and had a strong bond. In reality, Tony was constantly cheating on his wife and Carmella was looking for independence from Tony. She was also madly in love with Tony’s driver/bodyguard, Furio. They had their problems but Tony would always buy his way out of trouble. For example, he purchased a gorgeous summer home for the family. The relationship imploded when one of Tony’s mistresses called Carmella. Carmella flipped out and when Tony arrived home all of his belongings were on the driveway. The episode featured James Gandolfini and Edie Falco putting on one of their best performances. Tony and Carmella fought and expressed their issues with each other. It was heartbreaking to see the relationship end, even if it was inevitable. In the end, Tony and Carmella actually separated but later got back together.

10 The Death Of Sal Bonpensiero

Tony Soprano and “Big P*ssy” Sal Bonpensiero (Vincent Pastore) were best friends. Sal was a top earner in Tony’s crew and Tony considered him to be one of his most loyal and valuable friends. Sal was in fact an FBI informant trying to save himself and his family.

Throughout season 2, Tony became more and more suspicious of Sal. His suspicion proved right after he had an intense fever dream. In the dream he sees Sal as a dead fish telling him he’s an informant. That wasn’t enough proof until Tony discovered Sal’s wire. In the season 2 episode, “Funhouse”, Tony, Paulie and Silvio took Sal on a ride on Tony’s new boat. The heartbreak occurs when Tony finally confronts Sal. Sal realizes that his life is in danger but there isn’t anything he can do about it. He pleads for his life but then asks not to be shot in the face. All three unload their guns on Sal killing their friend. They throw his body off the boat and its never found. However, Tony is haunted by this heartbreaking death for the rest of the series.

9 The Death Of Vito Spatafore

Vito Spatafore (Joseph R. Gannascoli) was a ruthless gangster and top earner in Tony’s crew. He was also a closeted homosexual who struggled with coming out. He feared that his friends would judge him harshly and most likely kill him. He was married to Phil Leotardo’s cousin. When Tony finds out the truth about Vito he tries his best to be understanding and spare Vito’s life. This angers some of his friends and Phil. Vito runs away to New Hampshire and tries to start a new life. However, he clearly misses the life of a mobster and returns to Jersey. Phil finds out and brutally murders Vito.

It’s heartbreaking that he couldn’t be himself and when he tried to he was killed. Furthermore his wife and kids struggle after his death. In particular, Vito Jr. is teased and rebels against his family. This leads to Tony convincing his mother to send him away. Vito’s death and his family’s struggle is sad and heartbreaking.

8 The Death Of Livia Soprano

Throughout the first two seasons, Tony struggled to have a good relationship with his mother, Livia Soprano (Nancy Marchand). She was cold, domineering and cruel. She was difficult with Tony no matter what he tried. With his mother’s best interest in mind he put her in a retirement home but she didn’t see it that way. She was so angry with what she perceived as unfair treatment that she conspired with Uncle Junior to kill Tony. However, the hit was botched and Tony survived. The relationship became even more strained when Tony found out she was behind the attempt on his life. They rarely spoke to each other in season 2 but at the end it was established that she was going to be a witness against Tony in season 3 for stolen plane tickets. However, actress Nancy Marchand died before the start of the third season because of cancer. Her character appeared in season 3 using CGI and footage from the previous season. Livia died in the season 3 episode, “Proshai Livushka”. Tony struggled to hide his joy and relief over her death. The true heartbreak is the loss of such a great actress and character.

7 The Death Of Christopher Moltisanti

Christopher Moltisanti (Michael Imperoli) was a cousin of Carmella’s and an important part of Tony’s crew. Tony was very close with Christopher’s father and considered Christopher his nephew. Christopher was initially going to take over the New Jersey Crime Family. However, Christopher struggled with alcohol and drug addiction, which caused Tony to lose trust in Christopher. Also, Christopher’s fiancé Adriana, was working for the FBI and that further complicated Tony and Christopher’s relationship. Things continued to get strained between them until it finally reached a breaking point.

In the season 6 episode, “Kennedy & Heidi”, it featured one of the most heartbreaking and shocking deaths in the series. Tony and Christopher are in a terrible car accident with Christopher’s condition being far worse. Christopher was driving but Tony was unaware that Christopher had fallen off the wagon and was high. In the moment, instead of calling for help, Tony suffocated Christopher and killed him while he was still sitting in the driver's seat. It was shocking and heartbreaking to see Tony kill one of the most beloved characters in the series.

6 The Death Of Bobby Baccalieri And Silvio Dante’s Coma

In the final season of The Sopranos, Tony and his crew found themselves in a war with Phil Leotardo (Frank Vincent) and his New York family. Phil wanted to completely wipe out the entire Soprano crew. In the second last episode, “The Blue Comet”, Phil targeted the top earners and advisors in Tony’s crew. The episode featured a dual heartbreaking moment that shocked fans and made them cry. As Silvio Dante (Steven Van Zandt) leaves the Bada Bing, he’s ambushed and shot several times. He doesn’t die but the series ends with him in a coma. It’s sad to see Gabrielle Dante (Maureen Van Zandt) taking care of her husband in his vegetative state. However, even more heartbreaking is the tragic death of Bobby Baccalieri (Steven Schirripa).

Bobby was one of the most beloved characters in the series. He wasn’t like the other gangsters. He was sweet, kind and caring. At the beginning of the episode he asked his son to hangout with him and play with his toy trains. His son refuses telling him that’s kid stuff. Bobby is heartbroken that his son is growing up and drifting away but he wasn’t as heartbroken as the fans were about to be. Bobby attempts to buy a toy train, the blue comet, as he does gunmen enter the shop and gun him down. Bobby’s death is one of the most heartbreaking, not just to fans but to the characters in the series as well.

5 Dr. Melfi Attacked

Dr. Jennifer Melfi was Tony’s therapist. She was very dedicated to her job and tried to help everyone she could. She cared about Tony as she does all of her patients but also feared him as she was aware of his criminal behavior. In the season 3 episode, “Employee of the Month”, she is brutally r*ped in the stairwell of her building. It’s a heartbreaking moment but is also one of the most shocking and uncomfortable in the series. She believes in the police and the justice system, however they fail her. She struggles with trying to understand that pain she feels and how she was let down by the justice system. She realizes that she does have one other option, and that is Tony. She knows he will do anything for her and she knows that he’ll kill the person that hurt her. However, in the end she chooses not to tell him and tries to move on with her life.

4 The Series Finale

The series finale of The Sopranos is considered to be both brilliant and controversial. The final episode, “Made in America”, featured the Soprano family meeting at a diner. Tony plays the song, “Don’t Stop Believin”, on the jukebox as he waits for the family. Meadow (Jamie Lynn Sigler) is the last to walk in and suddenly the screen cut to black. Many thought that something was wrong with their cable but in fact, that was the ending. Many fans of the series speculate that the reason it cut to black was because Tony had been killed. Others dispute the fact pointing to the song that was playing as a hint that Tony is alive.

Regardless, it’s such a heartbreaking moment for several reasons. It’s the final episode of one of the greatest TV series, which is sad itself. Also, the idea of Tony Soprano dying is heartbreaking and would mean the show would never return. However, the true heartbreak is in the fact that James Gandolfini died in 2013. The end of the series and possible death of Tony combined with the death of James Gandolfini is truly heartbreaking.

3 The Lonely Life Of Junior Soprano

Corrado “Junior” Soprano (Dominic Chianese) was Tony’s Uncle and was at one point the head of the crime family. However, he was just a figurehead as Tony was the one really in charge. Initially, Junior is greedy, conniving and ruthless. Later, his character softens due to his illness and becomes more sympathetic. Junior was never married and had no kids. All he had was being a gangster and the closest thing he had to a son would be Tony and to a certain extent, Bobby. Junior ended up serving some time in jail and was under house arrest. He began to suffer from dementia. Tony refused to put his Uncle into a home and felt that family should take care of each other.

In the season 6 episode, “Members Only”, Junior shot Tony thinking he’s an old rival. Tony ends up in a coma and Junior is completely shutout of the family. Not even Bobby is allowed to have any contact with him. Junior ends up in a psychiatric home and his dementia worsens. Soon Junior has nobody, no friends and no family. He’s alone and can barley remember who he is. Tony visits Junior in the final episode and Junior can’t recognize Tony. It’s heartbreaking to see Uncle Junior in that state completely alone and barley able to recognize his family.

2 The Death Of Adriana La Cerva

The image of Adriana crawling away from Silvo Dante as he prepared to kill her is one of the most heartbreaking moments in the series. Adriana La Cerva (Drea de Metteo) was the fiancé of Christopher Moltisanti and ran the club, Crazy Horse. She was a loving, caring and loyal girlfriend. She was always there for Christopher but things got complicated when she was forced to become an FBI Informant. This caused her great stress and several health issues, including IBS. In the season 5 episode, “Long Term Parking”, she finally told Christopher that she was an FBI informant. Christopher was torn between the woman he was in love with and the life of crime he chose. Christopher betrayed her and told Tony. Tony cared deeply about Adriana but there is nothing worse than a rat to him. They told her that Christopher relapsed and was in the hospital after trying to kill himself. Silvo picked her up and drove her to see Christopher but he suddenly pulled over into the woods. She immediately knew what was going on and tried to get away. However, she couldn’t get away and the gunshot echoed in the woods.

1 AJ Attempts Suicide

AJ Soprano (Robert Iler) was a spoiled brat that was lazy and unmotivated. He was expelled from his high school, dropped out of college and slacked off at his Blockbuster job. However, that all changed for AJ when he fell in love with Blanca Selgado (Dania Ramirez).

For a while AJ was focused and motivated to take care of Blanca and her son. Everything came crashing down when Blanca broke up wit AJ. He was devastated by the breakup, which resulted in him becoming depressed and suicidal. In the season 6 episode, “The Second Coming”, AJ could no longer handle life and attempted suicide. He tied a cinder block to his leg and put a plastic bag over his head then jumped into the family pool. He immediately regretted his decision and tried to escape but couldn’t. Tony came home to find his son and pulled him out of the pool. The whole scenario is heartbreaking but the moment that really pulls on the heartstrings is when Tony holds a crying AJ.

At first he’s furious but AJ sobs and soon Tony tightly hugs his son and consoles him, calling him his baby. In another heartbreaking moment, Tony, Carmella and Meadow take AJ to the hospital. Carmella breaks down and cries as her son is wheeled away. It's one of the saddest and most heartbreaking situations in the entire series.

Sources: IMDB

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16 Most Heartbreaking Moments From The Sopranos