Airing between 1999 and 2007 for a total of six seasons, The Sopranos was a revolutionary television show that helped change the medium forever. It's not even a bold claim to say that The Sopranos is one of the best shows of all time, if not the best. It's rare to find critics or viewers - either back when the show was airing or nowadays - who aren't enthusiastic about it, with its cinematic presentation, complex characters, expert use of music, and highly engaging storylines making it essential TV.

It's also remarkable how The Sopranos features very few moral - or even just decent - characters, yet they remain compelling despite their faults, or maybe because of them. It's a surprisingly emotional show at times, thanks to the way it humanizes many of its characters, even when they do terrible things. As such, there are quite a few sad episodes of The Sopranos that may prove tearjerking to some viewers, with the following episodes of the show being among its saddest.

10 “Long Term Parking”

Season 5, Episode 12 (2004)

While it's true that most characters in The Sopranos are flawed people (especially its endlessly interesting and complex protagonist), there were a few genuinely good people within its large cast. Few were as kind as Adriana, who genuinely loved Tony's nephew, Christopher, despite how awful he often was to her, and who got targeted by the FBI for use as an informant because of her vulnerability.

Informing on the mob is seen as an unforgivable sin by those within it, and though Adriana was forced into being a "rat" by the FBI threatening imprisonment for drug charges, she wasn't saved from the fate that befalls informants. "Long Term Parking," the penultimate episode of the penultimate season, sees her betrayed by Christopher when he finds out about the FBI, and she's later executed by Tony's consigliere, Silvio. It's one of the hardest-to-watch episodes of the entire show.

9 “The Blue Comet”

Season 6, Episode 20 (2007)

For the last couple of seasons of The Sopranos, there was a constantly simmering conflict between gangs that seemed perpetually ready to explode. Things take until the penultimate episode of the final season, "The Blue Comet," before the tension between the Jersey and New York crews gives rise to all-out war on the streets.

The biggest casualty of the episode is Bobby Baccalieri, a loyal member of Tony's crew who'd been a part of the show since the second season. Of all the mobster characters, he was the most kind-hearted, meaning it's brutal to see him gunned down while he's engaging in one of his hobbies: trying out a vintage train set.

8 “Funhouse”

Season 2, Episode 13 (2000)

The final episode of the show's second season, "Funhouse," marked the first time a series regular got taken out. Salvatore 'Big Pussy' Bonpensiero wasn't exactly a good person by any means, but it's possible to feel a little sorry for him after falling prey to the FBI a couple of years before Adriana did.

Like Adriana, Big Pussy's status as an informant meant he was marked for death the instant Tony and the others in his crew found out. It's one of the few gang-related killings on the show that the murderers seem pained by, with Paulie telling Big Pussy, "You were like a brother to me." "To all of us," Tony adds, shortly before they make their ex-friend and colleague sleep with the fishes.

7 “Made in America”

Season 6, Episode 21 (2007)

As The Sopranos progresses as a show, things gradually become bleaker, with many characters ending in a worse place than where they started. There tended to be more frequent comic relief in the earlier seasons, and the later seasons in comparison feel deadlier, more unsettling, and colder, with part of that being the fact that by the final season, colors were generally more muted and things felt more wintry.

That makes "Made in America," the show's finale, naturally feel very downbeat. Every main character has lost at least one person they were close to, and the frequent casualties of the show mean that few are even left to populate the finale. It also contains a particularly heartbreaking final scene between Tony and Uncle Junior where the latter is shown to have completely succumbed to dementia, and no longer remembers who he is.

6 “Whitecaps”

Season 4, Episode 13 (2002)

Season 4 of The Sopranos concludes with "Whitecaps," and it's arguably the most emotionally heavy episode of the show that doesn't feature a major character's death. But at the same time, something is shown to die in "Whitecaps," at least temporarily: Tony and Carmela Soprano's marriage.

Carmela reaches her breaking point when it comes to Tony's infidelity, and much of the episode is spent with the two fighting, and it eventually ends in them splitting up. The acting between James Gandolfini and Edie Falco is incredibly intense, raw, and believable, making this a taxing and devastating episode, albeit an undeniably excellent one.

5 “Soprano Home Movies”

Season 6, Episode 13 (2007)

It turns out that seeing Tony crush Bobby Baccalieri emotionally in "Sopranos Home Movies" is almost as heartbreaking as seeing him meet his demise in "The Blue Comet." During a cabin getaway, a fight erupts between the two, and Tony punishes Bobby by making him carry out a hit.

Tony's the boss, and so Bobby has to obey, even though he's never killed anyone before and Tony knows it will impact him emotionally. It's crushing to see Bobby forced to do something so heinous, with the show making it clear that doing so hurts him more than the act of killing impacts other members of Tony's gang.

4 “Stage 5”

Season 6, Episode 14 (2007)

Things don't go well for Johnny Sack in the final season of The Sopranos. He's arrested, imprisoned, effectively loses control of the New York crew (which has bad implications for almost everyone), and eventually develops lung cancer, which is what ends his life in "Stage 5."

After seeing so many characters meet violent ends (some of them tragic), it's somewhat jarring to see someone die of something more common in everyday life. Like other flawed characters in the show, Johnny Sack wasn't a great person, but he had likable traits (such as his devotion to his wife and kids), and certainly wasn't anywhere near as terrible as Phil Leotardo (who took his place as head of the New York crew), making his death a tough one to watch.

3 “University”

Season 3, Episode 6 (2001)

The Season 3 episode "University" does a remarkable job of getting viewers invested in a one-off character in The Sopranos who meets a horrible fate by the end of the episode she first appears in. That character's Tracee, who's notable for being one of the only strippers at the infamous Bada Bing to get some form of characterization, with her cruel end demonstrating how little respect many of the show's characters have for women.

She's cruelly beaten to death by the monstrous Ralph, who doesn't seem fazed by what he's done, despite Tracee being pregnant at the time with his unborn child. It's a genuinely traumatic episode, with its awful display of violence against a deeply sympathetic - and innocent - one-off character being hard to forget.

2 “The Second Coming”

Season 6, Episode 19 (2007)

Throughout all six seasons of The Sopranos, Tony is shown to struggle with depression and anxiety, and it's the main reason why so many scenes show him in therapy with Dr. Melfi. It also makes it tragic to see Tony's son, A.J., begin to exhibit signs of depression himself as he grows older (potentially hereditary), with him reaching rock bottom towards the end of the final season.

In the show's third-last episode, "The Second Coming," A.J. even attempts to take his life by drowning himself, with Tony luckily being there to save him. A.J. isn't always a likable character, but seeing anyone his age suffer from depression to that extent is harrowing, and seeing his parents react with distress (again, with phenomenal acting by Gandolfini and Falco) also proves hard to watch.

1 “Join the Club”

Season 6, Episode 2 (2006)

In the shocking Season 6 premiere titled "Members Only," Tony is shot by a dementia-affected Uncle Junior. The next two episodes have him in a coma, where viewers see Tony's vivid and surreal near-death dreams while also seeing those close to Tony try and come to terms with the fact he may not wake up.

"Join the Club," the season's second episode, is particularly heartbreaking because of the time it spends with Carmela. Again, at the risk of sounding redundant by praising Falco yet again: she's incredible here, with her tearful, nostalgia-tinged monologue to a comatose Tony (backed by Tom Petty's "American Girl") proving to be one of the most emotional (and underrated) scenes in the entire show.

NEXT: The Best Episodes of 'The Sopranos,' According to IMDb