This week marks the 25th anniversary of The Sopranos, one of the all-time great dramas that helped put HBO on the map with its original series. There were HBO shows before The Sopranos, but this is the one that was a breakout hit, and it increased HBO’s prestige and standing in the industry. Series creator David Chase had made his name in network television, but no other shows like The Sopranos existed. It was R-rated television in an era before that was a common occurrence.
The Sopranos also made its leading man, the late James Gandolfini, a star for his performance as Tony Soprano, a family man and mob boss who is forced into therapy when his anxiety completely overwhelms him. That set off a six-season run that firmly established The Sopranos‘ place in TV history. In honor of the show’s 25th anniversary, we’re sharing our picks for the 10 best episodes of The Sopranos.
10. All Due Respect (Season 5, Episode 13)
Steve Buscemi had a season-long arc as Tony Blundetto, Tony Soprano’s cousin. But once Tony B made an enemy out of Phil Leotardo (Frank Vincent), it was only a matter of time before his ticket would be punched. The surprise is that Tony Soprano did the deed himself, especially after going to great lengths to protect Tony B from Phil’s revenge. Tony’s “mercy” killing of his cousin only made Phil feel cheated of his revenge, which led to the all-out mob war in the final season.
This episode also memorably ended with Tony literally running from the FBI as they came to arrest his New York counterpart, Johnny Sack (Vincent Curatola). But even Tony Soprano can only run for so long.
9. Whoever Did This (Season 4, Episode 9)
After his appearances in The Matrix and Memento, Joe Pantoliano had a lot of experience playing weasels. None more so than his character in The Sopranos, Ralph Cifaretto. From the first second that Ralph appeared on screen, it was practically inevitable that Tony would be the one to murder him. Regardless, the exact details of why Tony killed Ralph were still surprising.
Earlier in the season, Ralph murdered Tracee (Ariel Kiley), a stripper at the Bada Bing! strip club. But it wasn’t until Tony’s beloved horse, Pie-O-My, died in a very suspicious fire that Tony was finally moved to kill Ralph. Even as it happens and Tony explains why he’s so angry, we’re not sure if he was talking about Tracee’s death or the horse’s demise.
8. Employee of the Month (Season 3, Episode 4)
Lorraine Bracco finally got a spotlight episode as Tony’s therapist, Dr. Jennifer Melfi, and it’s a harrowing morality play. Melfi is brutalized and raped by a man who gets away with his crimes because the police screwed up the evidence. Melfi is later physically sickened when she sees that the man who raped her was “employee of the month” at a local sub shop.
The question that Melfi struggles with is if she should bring this information to Tony, the one man she knows who could get revenge on her rapist. The entire episode masterfully builds to the final moment of the hour when Melfi makes her decision.
7. Whitecaps (Season 4, Episode 13)
If the season 4 finale, Whitecaps, had been the true end of Tony’s marriage to Carmela (Edie Falco), it would have been a fitting conclusion to their union. Four seasons of Tony’s infidelities, Carmela’s wandering eye, and mutual lingering resentments finally come out as Gandolfini and Falco go head-to-head in absolutely vicious arguments.
Tony may have been the one who had multiple affairs, but Carmela is far from blameless. She even confesses her feelings for Tony’s former enforcer, Furio Giunta (Federico Castelluccio), which could have gotten him killed if he had been within Tony’s reach. This was a major turning point in the series, even though Carmela and Tony eventually reconciled.
6. The Blue Comet (Season 6, Episode 20)
In the penultimate episode of the series, The Sopranos goes full Godfather as Tony makes his move against Phil … and fails. The retribution from the New York mob is sudden and fierce, and two long-time characters were either killed or seriously wounded in some of the most shocking moments of the show to date.
Because this was so close to the end of the series, no one was safe. That point was brought home by the way that Tony clutched his riffle in the closing moments while lying in bed wide awake.
5. The Sopranos (Season 1, Episode 1)
This was the episode that changed TV forever. Although hardcore Sopranos fans tend to prefer the episodes that came after the pilot, this was an incredibly effective setup for the show. It introduced Tony and his family, as well as his debilitating panic attacks that led him to seek therapy from Dr. Melfi.
The Sopranos also took the time to establish Tony’s strained relationships with both his uncle, Corrado Soprano, Jr. (Dominic Chianese), and his mother, Livia Soprano (Nancy Marchand), both of which came to a head at the end of the first season. The pilot itself could have worked as a self-contained story, but The Sopranos wouldn’t have had the same impact if it had simply been a movie.
4. Long Term Parking (Season 5, Episode 12)
Once the FBI forced Adriana La Cerva (Drea de Matteo) to be their informant, her time on the show was ticking away. However, this long-term story allowed De Matteo to infuse Adriana with a more compelling performance as the proverbial walls closed in on her. Adriana’s time ran out in Long Term Parking when the FBI tried to make her wear a wire. In turn, she offered to get her fiancée, Christopher Moltisanti (Michael Imperioli), to flip on Tony.
The irony is that Christopher could have ultimately saved his own life if he had turned against Tony and escaped with Adriana into witness protection. Instead, he sacrificed Adriana to shore up his position with Tony, which led to a devastating off-camera death for Adriana. Ultimately, it only bought Christopher a little more time before he met his own fate.
3. Funhouse (Season 2, Episode 13)
Salvatore “Big Pussy” Bonpensiero (Vincent Pastore) was the first big rat in Tony’s crew, but not the last. As illustrated above, Tony was not tolerant of anyone who turned on him. By this point, even Tony’s dreams were telling him that Big Pussy had flipped, before making another famous Godfather reference to sleeping with the fish.
The striking thing about this episode is that Big Pussy’s fate is never in doubt, and yet the scenes leading up to his execution are full of dramatic tension. The Sopranos was already at the top of its game here, and the show only improved.
2. Pine Barrens (Season 3, Episode 11)
Pine Barrens is one of the most popular episodes of The Sopranos largely because it left fans hanging about the fate of the Russian, Valery (Vitali Baganov). In retrospect, this was where we should have realized that Chase was going to end the show on an ambiguous note, since the series never resolved what happened to Valery after Paulie Gualtieri (Tony Sirico) and Christopher accidentally let him get away.
People forget that Valery owed money to Silvio Dante (Steven Van Zandt), which is why Paulie and Christopher met him in the first place. It’s also Paulie’s fault for starting a fight with Valery, which led to his and Christopher’s darkly hilarious misadventures as they nearly freeze to death while searching for Valery. Any other show would have eventually brought back Valery for closure. Chase and company just wanted us to suffer. And it must have worked, because we’re still talking about this episode over 20 years after it aired.
1 . College (Season 1, Episode 5)
A single moment in College elevates it above the rest of The Sopranos. It’s a quiet scene between Tony and his daughter, Meadow (Jamie-Lynn Sigler), shortly after Tony has brutally murdered Fabian “Febby” Petrulio (Tony Ray Rossi), yet another rat who went running to the feds. Meadow can see that Tony’s been in a fight, but he lies to her face about his injuries, and she knows that he’s lying. But Meadow still tearfully tells her father that she loves him.
Earlier in the episode, while taking Meadow to visit a potential college, Tony and his daughter have perhaps their first honest conversation about his life in the mafia. It actually strengthens their bond. Yet Tony, being Tony, can’t resist the urge to mix his family life with his other family life when he spots Febby living in witness protection. So, Tony sneaks away to murder Febby before reuniting with his daughter.
It doesn’t matter that Febby was on the verge of killing Tony before he was cornered himself. This game-changing moment helped usher in television’s era of antiheroes. If Tony’s inner darkness wasn’t clear from the start, it was now.
Watch The Sopranos on Max.
