When “The Sopranos” hit the airwaves in 1999, it was like a bullet to the kneecaps of network TV dramas, which looked like reruns of “Sesame Street” next to the hard-R sex, violence, and language permitted on premium cable. Created by David Chase, it hooked audiences with the delicious premise of a mob boss, Tony Soprano (James Gandolfini), seeking therapeutic help when his problems at work and home give him panic attacks. (Funnily enough, the comedy “Analyze This,” starring Robert De Niro as a mobster who attends sessions with therapist Billy Crystal, opened in theaters that same year.)
“The Sopranos” solidified HBO’s reputation as the home of prestige television, winning 21 Emmys throughout its six season run, and topped TV Guide’s list of the 60 greatest TV shows of all time. With its dense storytelling, multi-dimensional characters, and high production value, the series set a new benchmark for TV dramas. Shows like “The Wire,” “Breaking Bad,” and “Mad Men” would be unthinkable without the ground “The Sopranos” broke.
Yet its historical importance would be zilch if not for the fact that it remains significant in popular culture. Years after its finale aired in 2007, Tony Soprano memes persist online, and the series continues to garner new generations of fans thanks to streaming. Here are the 15 best episodes of “The Sopranos” ranked, based on IMDb ratings and fan lists, their importance to the show’s history and overall arc, and the author’s own knowledge.
15. Employee of the Month (Season 3, Episode 4)
After being raped, Dr. Jennifer Melfi (Lorraine Bracco) is angered when her attacker is released due to a technicality. After spotting her rapist at a restaurant where he’s just been named employee of the month, she has a dream in which he is attacked by a Rottweiler, which she relates to her psychiatrist, Dr. Elliot Kupferberg (Peter Bogdanovich). Dr. Kupferberg immediately interprets this as representative of Tony, and she contemplates siccing him on her rapist. Meanwhile, Tony’s sister, Janice (Aida Turturro), is attacked by Russian mobsters looking for the prosthetic leg she stole from her late mother’s caregiver, Svetlana (Alla Kliouka Schaffer).
When their sessions began, Dr. Melfi saw Tony as a deeply troubled man who used violence as a means of dealing with trauma. Yet when she is the victim of a crime, she shows that she is not above using violence herself when the justice system fails her. Although she doesn’t act upon it, her desire shakes her, as she suddenly sees Tony as a protector. That furthers plays out in the Janice subplot, as Tony must again come to his sister’s defense.
14. Kennedy and Heidi (Season 6, Episode 18)
As he’s driving with Tony, Christopher Moltisanti (Michael Imperioli) gets into a car crash and is severely injured. Realizing his cousin is once again using heroin, Tony suffocates him and tells his family he died instantly in the crash. Although he has a dream in which he admits the truth to Dr. Melfi, he instead complains about him in his next therapy session. Disgusted by the grief displayed at the funeral, Tony takes off for Vegas, where he meets up with one of Christopher’s favorite strippers, Sonya (Sarah Shahi), and take peyote. He has an epiphany while watching the sun rise, which is extra-illuminated by some toxic waste he’s dumped into a lake in New Jersey.
There were many deaths throughout the run of “The Sopranos” (comes with the territory), yet few were as devastating as Christopher Moltisanti’s. Christopher was both Tony’s closest ally and his greatest burden, and anyone who has watched a loved one struggle with drug addiction will instantly recognize the mix of love and frustration he has for him. It’s what makes their final moments together feel so tragic and inevitable.
13. Amour Fou (Season 3, Episode 12)
As Carmela Soprano (Edie Falco) awaits test results for ovarian cancer, Tony tries to break things off with his unstable mistress, Gloria Trillo (Annabella Sciorra). When Gloria runs into Carmela, she calls the Soprano household and threatens to spill the beans about their affair, prompting Tony to nearly kill her. Meanwhile, Jackie Aprile Jr. (Jason Cerbone) tries to prove himself by robbing a card game populated by made men, causing a riff between Tony and Ralph Cifaretto (Joe Pantoliano) as to how to deal with the rambunctious kid.
Tony’s serial infidelity has often caused him problems, and it almost catches up with him when he starts seeing one of Dr. Melfi’s patients. Gloria suffers from what Dr. Melfi calls amour fou – “crazy love” — and she eventually kills herself after Tony sends one of his henchmen to threaten her life. Although Tony gets away scot-free, his actions once again have a devastating effect on someone else. Similarly, his youthful robbery of a mob poker game inspires Jackie Jr. to try and do the same, sealing his own tragic fate.
12. I Dream of Jeannie Cusamano (Season 1, Episode 13)
Tony warns Dr. Melfi to go into hiding after his uncle, Junior Soprano (Dominic Chianese), puts out a hit on him. As Tony consolidates his power against Junior, he tells his crew about his therapy sessions, and they re-affirm their support for him. Tony refuses to believe that his mother, Livia Soprano (Nancy Marchand), was behind the attempt on his life until the FBI presents him with tape-recorded evidence of her conspiring with Junior. He goes to the hospital to kill her after she suffers a stroke, but nurses intervene before he can.
One of the most complicated relationships in the early years of “The Sopranos” was between Tony and Livia, and that dynamic came to a sudden end when Marchand died between Seasons 2 and 3 (her storyline was wrapped up through computer-generated face replacement). Though tragically brief, her performance left an indelible impression on the series, and provided important context to Tony’s many issues with women. Tony nearly kills Dr. Melfi when she suggests Livia might be suffering from borderline personality disorder, showing how fiercely he will defend her even in the face of reality.
11. The Second Coming (Season 6, Episode 19)
A.J. Soprano (Robert Iler) unsuccessfully tries to drown himself in the family pool after reading William Butler Yates’ poem “The Second Coming,” prompting frustration and sympathy from Tony. He and Carmela take their son to a family therapist, where he recounts upsetting memories about his grandmother Livia’s depression. Tony is angered when Dr. Melfi suggests that A.J.’s suicide attempt was a cry for help, insisting that he glimpsed something beyond existence while in Las Vegas escaping guilt for Christopher’s death.
Few “Sopranos” characters inspire as much consternation as A.J., whose teenage angst is amplified by his father’s violent line of work. Tony is often angered by his son’s inability to grow up and “be a man,” i.e. a version of himself at that age. Yet when A.J. attempts suicide, it awakens paternal instincts in Tony, which are further amplified when he curb stomps a rival gang capo who threatens Meadow (Jamie-Lynn Sigler). A.J.’s memories of Livia’s depression also highlight the generational trauma that has been passed down throughout the Soprano family, with the vicious cycle of abuse being repeated.
10. Irregular Around the Margins (Season 5, Episode 5)
Tony avoids acting upon a sexually tense moment between him and Christopher’s girlfriend, Adriana La Cerva (Drea de Matteo), taking it as a sign of personal growth. Yet that flies out the window when Tony and Adriana get into a car crash while en route to score cocaine. Rumors spread about an alleged sexual act that precipitated the crash, causing Christopher to relapse. Prepared to kill his cousin, Tony instead takes him to the doctor who treated them to tell him the truth, later complaining to Dr. Melfi that he might as well have slept with Adriana for all the trouble it caused him.
Tony’s constant philandering was one of many signs of his narcissism, and it is a sign of personal growth that he refuses to commit an act that could cause irreparable harm. Yet when he’s placed in a compromising situation, he falls back on his old ways, pressuring Adriana to lie about why they were in the car together in the first place. It’s one of many signs that as much as Tony changes, he stays the same.
9. The Knight in White Satin Armor (Season 2, Episode 12)
As tensions rise between Tony and Richie Aprile (David Proval), Richie tries to put a hit out on him, which Junior quashes by ratting him out. But before Tony can get his hands on Richie, Janice shoots him after a lover’s quarrel turns violent. Tony arrives to clean up Janice’s mess, getting her out of New Jersey while things blow over. He later pays a visit to Livia for the first time since they each tried to have the other one killed, but they remain at polar opposites.
As “The Sopranos” grew in popularity, there was no shortage of famous actors who wanted to make guest appearances, many of whom had a history of playing mobsters. Case in point: David Proval, who got his start as one of the low-level hoods in Martin Scorsese’s “Mean Streets,” and brings that history to the role of Jackie Aprile’s (Michael Rispoli) older brother, who immediately causes trouble after getting released from prison. He’s a thorn in Tony’s side to the very end, as even his death causes issues with Tony’s sister.
8. Whoever Did This (Season 4, Episode 9)
When his son suffers brain damage during an archery accident, Ralphie believes God is punishing him for his misdeeds, and he tries to do right by the Aprile family. Later, the stable housing Tony’s prized racehorse, Pie-O-My, burns down, and coincidentally, the insurance money that’s paid out just happens to be enough to cover Ralphie’s growing medical expenses. Tony confronts him about this, and ends up strangling Ralphie to death. Meanwhile, Junior tries to get out of legal culpability in his trial by feigning memory loss, which he begins to actually experience.
One of the most beloved guest stars throughout the run of “The Sopranos” was Joe Pantoliano, who won an Emmy as best supporting actor in a drama series for the show’s fourth season. It was a fitting capper for a multi-season performance as capo Ralphie Cifaretto, who momentarily gains our sympathy when his son is hurt, only to remind us why he’s so odious. Ralphie schemes to gain power through a variety of means, including dating Jackie Aprile’s widow, Rosalie (Sharon Angela) — yet in the end, he’s no match for Tony.
7. All Due Respect (Season 5, Episode 13)
As the riff between the New Jersey and New York crime families continues to grow, Tony’s cousin, Tony Blundetto (Steve Buscemi, who also directed several episodes), get caught in the crosshairs. New York capo Phil Leotardo (Frank Vincent) is hunting Tony B., and Tony S. pushes back on allegations that he’s allowing his personal relationship with his cousin to cloud his judgment about what is best to ease tensions. Knowing that Tony B. will be tortured when Phil finds him, Tony S. quickly kills him before giving away his location.
Buscemi’s performance as Tony B. is one of the great tragic arcs in the history of “The Sopranos.” Tony B. tries to go straight after getting out of prison, but it doesn’t take long for him to fall back on his old ways. As his actions threaten to destabilize relations with New York boss Johnny Sack (Vincent Curatola), Tony S. is forced to choose between loyalty to his cousin and loyalty to his rivals. In the end, he does the most humane thing he can think of, sparing his cousin unnecessary pain while temporarily making peace.
6. Made in America (Season 6, Episode 21)
After some finagling between the families, Tony finally manages to have Phil killed, thus ending their violent feud. Yet Tony isn’t completely out of the woods, as he suspects Carlo Gervasi (Arthur J. Nascarella) has turned informant. He pays Junior a visit in the nursing home to convince him to give his money to Janice after her husband, Bobby Baccalieri (Steven R. Schirripa), is killed. But Junior has no memory of Tony, Bobby, or his involvement with the mafia due to his dementia. Tony meets his family for dinner, where a mysterious man has been parked outside the restaurant.
The last episode of “The Sopranos” has caused endless debate since it first aired in 2007. Who could ever forget that cut to black when the door opens and Tony looks up to see if it’s his daughter or his assassin coming inside. The cut was so abrupt that you’d be right to assume your television had gone out, yet that was indeed the final shot. Did Tony die? Probably, but that hasn’t stopped us from guessing since.
5. Funhouse (Season 2, Episode 13)
After contacting food poisoning, Tony has a dream in which one of his closest allies, Sal “Big Pussy” Bonpensiero (Vincent Pastore), admits to being an FBI informant (albeit in the form of a fish). Tony and his capos, Silvio Dante (Steven Van Zandt) and Paulie Walnuts (Tony Sirico), take Pussy out on a boat to kill him and dump his body in the ocean — thus feeding him to the fishes. Later, Tony is arrested after giving Livia some scalped airline tickets he scored from David Scatino (Robert Patrick), which Dr. Melfi suspects was his way of getting back at his mother for trying to have him killed.
“The Sopranos” often indulged in dream sequences, pushing TV storytelling into the realm of the surreal. The dreams always served a narrative purpose, and in this case, it was Tony realizing he had to kill one of his oldest friends. Big Pussy getting whacked was the earliest indication that in the world of “The Sopranos,” no one was safe, and from then on out, audiences were constantly on edge as to who was next.
4. The Blue Comet (Season 6, Episode 20)
Things come to a head between Tony and Phil, as each orders a hit on the other. Dr. Melfi, meanwhile, decides she’s had enough of Tony and decides to stop treating him. After an attempted hit on Phil goes haywire, Phil has Bobby killed and puts Silvio in a coma. Tony orders Carmela and A.J. to go into hiding, and his frustration reaches a breaking point when his son starts crying about his Uncle Bobby’s murder. Tony ends up alone in a safe house, surrounded by the wreckage of his life.
In many cases, the penultimate episode of a show’s final season is more compelling than its actual finale, and that’s certainly the case with “The Sopranos.” Things are ramping up: Bobby, one of Tony’s kindest lieutenants, has been killed; his sessions with Dr. Melfi have come to an abrupt close; and his sister, Janice, is crumbling under the weight of Uncle Junior’s nursing home bills. It shows the full brunt of Tony’s actions coming down to bear upon him, and hints at the shattering climax soon to come.
3. Long Term Parking (Season 5, Episode 12)
When Adriana is found to have disposed of evidence from a murder, she tries to convince the FBI that Christopher can become an informer. After nearly killing her when she tells him about her relationship with the feds, Christopher agrees to start a new life with Adriana, only to back out when faced with the realities of an unhappy marriage. Told that Christopher has overdosed, Adriana gets a ride to the hospital from Silvio, only to be taken out to the woods and shot. Finding his cousin strung out on heroin, Tony beats Christopher up before returning home to Carmela after a lengthy separation.
Adriana’s fate was sealed from the moment she became ensnared by the FBI, but that doesn’t make her ultimate demise any less devastating. It’s all the more heartbreaking because Christopher sells her out, despite her being a loyal girlfriend throughout his worst moments. It’s yet another instance in which “The Sopranos” proves that a life of crime eventually catches up with everyone who engages in it, even those who only nibble at the margins.
2. Pine Barrens (Season 3, Episode 11)
As Silvio recovers from the flu, Christopher accompanies Paulie Walnuts to collect from a Russian who owes Tony some money. Things escalate to the point where they think they’ve killed the Russian, prompting them to drive his body out to the New Jersey Pine Barrens. Turns out the guy is still alive, and when he makes a run for it, Christopher and Paulie realize they’re lost when the Russian’s footprints disappear in the snow. Tony, meanwhile, admits to Dr. Melfi that he’s seeing her unstable patient, Gloria, and ignores the parallels she has with his late mother.
Although it dealt with issues of life and death, “The Sopranos” was often very funny, and at times could even be farcical. That’s certainly the case with “Pine Barrens,” in which Christopher and Paulie try to dispense with a Russian mobster in much the same way that Abbott and Costello would. Yet this humor doesn’t come out of nowhere: it’s based in the absurdity of making your living from stealing and killing people. As they nearly freeze to death, you can almost hear Christopher and Paulie asking themselves how they got here in the first place.
1. Whitecaps (Season 4, Episode 13)
As Tony tries to purchase a home on the Jersey Shore, his mistress, Irina Peltsin (Oksana Lada), calls Carmela to tell her that he slept with her cousin, Svetlana. Although she’s tolerated Tony’s infidelities when kept secret, this is the last straw for Carmela, and she kicks Tony out. He tries to get out of buying the new house, but the broker refuses to let him out of the contract unless he pays a fee. As tension escalate, Carmela tells Tony about her romantic feelings for Furio (Federico Castelluccio), which sends him into a jealous rage.
Although it hooked audiences in as a show about the mafia, “The Sopranos” was ultimately a story of family, and the ways in which Tony’s selfishness threatens to destroy his home life. There were many moments of graphic violence throughout the series, yet its most emotionally violent scene was the confrontation between Tony and Carmela over his constant cheating. It’s a heated one-on-one that sent chills down the spine of viewers who knew that this moment was inevitable, and remains the high watermark of the show’s many highlights.