Chefe da máfia e pai de família, Tony Soprano começa a ter ataques de pânico e decide procurar a ajuda de uma profissional, Dra. Jennifer Melfi. Ele discute sua intimidade e a vida no crime, revelando o desconforto da mulher, Carmela Soprano, com as suas atividades profissionais. Enquanto tenta proteger os filhos, Meadow e Anthony Junior, o mafioso irá enfrentar uma investigação federal e a possível traição de um membro da família.
Tony Soprano, o chefe da máfia de Nova Jersey, começa as sessões de terapia com a dra. Jennifer Melfi após ter sofrido ataques de pânico. Sua mãe, Livia, recusa-se a ir para um asilo. Seu tio quer usar o restaurante dos amigos de Tony para cometer um assassinato, mas Tony evita o crime explodindo o restaurante. Christopher Moltisanti, o sobrinho de Tony, extermina o porta-voz da máfia tcheca que estava tentando infiltrar-se nos negócios da família.
Christopher e Brendan Filone começam a roubar caminhões. Eles descobrem que o proprietário dos caminhões paga Junior por proteção, mas o vício em drogas de Chris e Brendan os impede de respeitar as ordens de Junior. Carmela pede a Tony um favor que envolve o carro roubado da professora de ciências de A.J.. Após vários incidentes, Tony força Livia a se mudar para um asilo, mesmo contra a vontade dela.
Os Sopranos contratam os Buccos para prepararem um jantar. A filha de Tony, Meadow, pede a Christopher e Brendan algo que a deixe acordada para preparar-se para os exames do SAT. Tony aceita a tarefa de assegurar o divórcio da filha de um judeu hassídico. Junior libera a retribuição a Christopher e Brendan pelo roubo dos caminhões.
Tony pede ao seu amigo, o detetive Vin Makazian, para seguir a dr. Melfi depois que ela apareceu em seus sonhos. Christopher pede vingança contra Junior e Mikey Palmice pela morte de Brendan. Surge a dúvida sobre quem será o sucessor de Jackie Aprile.
Tony e Meadow viajam para Maine para conhecer as faculdades, e eles discutem a natureza do “negócio” de Tony. Carmela luta contra uma gripe e busca conforto com Padre Intintola após descobrir que o terapeuta secreto de Tony é uma mulher. Tony encontra um antigo sócio que associou-se ao Programa de Proteção a Testemunhas e segue-o por “questões de negócios”.
Tio Junior é escolhido como o chefe da família DiMeo. Tony esquematiza uma maneira de convencer Junior a perdoar seu amigo judeu. O aniversário de 18 anos de casamento de Carmela e Tony vai de mal a pior. O Prozac que a dr. Melfi receitou a Tony começa a afetar sua libido apesar de seus sonhos recorrentes o levarem a se apaixonar por sua terapeuta.
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Tony invests in a land deal despite Carmela’s concerns about money. Junior faces his own financial woes as his trial approaches. Adriana brings her new friend to the Soprano Sunday dinner, but Adriana has no idea who Danielle is working for. Tony bonds with Christopher by giving him the opportunity to avenge the murder of his father.
With Paulie in jail, Christopher becomes acting capo, but he gets off to a bad start with Patsy. Still troubled by Jackie Jr.’s death, Meadow contemplates taking a year off from college to travel. Meanwhile, Adriana is in a bind after ending her friendship with Daniele, and Silvio discusses a misunderstanding at a Newark riverfront construction site.
Silvio and Ralph must take care of a planned protest of the Columbus Day parade by a Native American group. At an Italian pride ladies’ lunch, Carmela is embarrassed by anti-Mafia remarks. Meanwhile, Ralph deals with new relationship troubles, and Bobby receives some tough news.
A disparaging remark about his wife sets Johnny Sack off on a vendetta. Meadow decides to do volunteer work at the South Bronx Law Center; Furio hosts a housewarming party for the gang; Silvio and Chris make an offer to an old-time hit man named Lou DiMaggio; and Tony and Carmela find themselves at odds over the family’s bill-consolidation strategy.
Checking out Ralph’s promising new filly at the track, Tony displays a flair for horse-racing strategy–and discovers an unexpected affinity for the stable life. Adriana finds her rock club being used as a place of business for Chris and his pals. Meanwhile, a court artist incurs the wrath of Uncle Junior, and Janice feeds Bobby in his hour of need.
After hiring an attractive French hostess, Elodi, Artie agrees to loan her brother some money, with interest. Meanwhile, Christopher gets some new responsibilities; Carmela fixes Furio up with an oral hygienist; Anthony Jr. becomes the ‘dough boy’ of a new rich girlfriend; and Tony receives some unsettling news about an old acquaintance.
Tony and the gang throw Paulie a Bada Bing bash after his release from jail, but it doesn’t take long for old tensions to resurface. Carmela’s cousin Brian throws out a hypothetical investment scenario that Tony and Ralph attempt to turn into reality with the help of Assemblyman Zellman and a black community leader.
Paulie takes pains to integrate his mother Nucci into the social world at Green Grove. Meanwhile, Furio faces up to his inner feelings during a trip to Italy to see his ailing father; Ralph introduces Tony to his new ‘goomar,’ Valentina; and Carmela finds a new source of investment income.
After an aggressive team of reporters lowers the boom on Uncle Junior, his lawyers try a new strategy. Ralph has some fun at the expense of Paulie and his mother, but soon winds up with his own family problems. Meanwhile, Tony again finds refuge at the stables.
At therapy, Tony likens himself to the ‘sad clown,’ but Melfi doesn’t buy into his melancholy portrait. Meanwhile, Carmela drags A.J. with her to Furio’s house to offer decorating tips and companionship; Paulie puts the finishing touches on some free artwork; and Christopher finds himself at a crossroads.
After a sitdown with Carmine and Johnny Sack, Tony contemplates the future of the HUD partnership. Meanwhile, Paulie blows off steam with an old pal; Janice starts losing patience with the obsessive Bobby; and Melfi ponders the Freudian undercurrents of Tony’s latest dreams.
Tony continues to haggle with Johnny Sack and the two Carmines over the Esplanade profits. Carmela makes a decorating date she can’t keep; Furio proves a reluctant companion to Tony on a casino junket; Paulie plays an impatient chaperone to some ladies from the nursing home; and Meadow debates the true meaning of a literary classic with her mom.
In the Season Four finale, Tony and Carmela contemplate purchasing a shore house, but a voice from the past threatens the deal. While Uncle Junior breaks out the Hearty Burgundy, Little Paulie and Benny break in a new sound system on the Stugots. With Carmine apparently intent on putting the past behind him, Tony and Johnny Sack weigh their options, carefully.
A flood of organized crime parolees changes the landscape of the Soprano/Lupertazzi alliance. Janice carries on the family’s Sunday dinner tradition. Carmela and A.J. commune with local wildlife. Christopher balks at footing the bill on ‘goomar night.’ Tony tries to introduce Dr. Melfi to his ‘other’ self.
Tony sizes up a contractor’s gift, then reunites with his paroled cousin, Tony Blundetto. Paulie and Christopher relive some not-so-special memories. Carmela launches a film club. Adriana grapples with her guilt. A familiar figure ‘crosses over.’
Tony’s power-sharing plan doesn’t fly with Johnny Sack, who makes his point through a bookie named Lorraine Calluzzo. Out on parole, Feech La Manna crosses Paulie in his attempt to break into the landscaping business. Tony gets a roommate. Junior looks into the past while testing the patience of those closest to him.
Carmela and Tony reunite, if only to discuss Anthony Jr.’s dwindling college prospects. Feech takes Tony’s crew on a trip down memory lane. Lorraine’s allegiances get her into hot water. A.J. has a night to remember in the Big Apple.
While Christopher is away, Tony gives Adriana a ride home that proves disastrous. Meanwhile, the Soprano crew plays a game of ‘telephone’ with the story that turns it into something far more sinister when an enraged Christopher gets wind of it.
With her son’s future at stake, Carmela puts in some extra time with his college advisor, Robert Wegler. Meanwhile, Tony Blundetto realizes it’s hard doing business with strangers, and A.J. concludes there’s no place like home.
His father’s longtime goomar sheds light on some of Tony’s lingering emotional and financial mysteries. Meanwhile, Junior sees the upside of attending the funerals of fringe relations, while Christopher sees the downside of enabling an A.A. friend’s new addiction.
Friends and family gather at the Sopranos’ for a not-so-surprise 75th birthday party for Carmela’s father, Hugh. Meanwhile, Johnny Sack shows off his new wheels, Phil Leotardo pulls into Pussy’s old place for some auto repairs, and Tony B. considers accepting a familiar job on the side.
A rumor involving his cousin puts Tony’s relationship with Johnny Sack back on thin ice. Meadow helps get her boyfriend Finn a job. A.J. ponders a ‘maximum-security summer’ at Casa Carmela. Melfi links Tony’s current guilt to a past job. Carmela learns that good legal help is hard to find.
Tony B. and Christopher unearth some old memories during an otherwise idyllic trip to the country. Tony and Carmela plan another party. Janice lands in anger-management therapy after a sports-rage incident. Benny and Terry solve a missing-Vespa mystery. Tony puts his sister’s newfound serenity to the test.
Tony escapes to the Plaza Hotel for a night of rest and relaxation, but his dreams are haunted by past faces. Another casualty falls in the war between Johnny Sack and Little Carmine, and Tony B. heads to New York for revenge.
With the feds pulling a new trump card, Adriana ponders her options. Tony B. unloads some heavy baggage on Tony, and vice-versa. Johnny Sack makes Tony an offer he can refuse, and Tony offers Carmela a deal to make her real-estate dreams come true.
In the Season Five finale, Tony’s crew circles the wagons as Johnny Sack turns up the heat. Carmela counts her blessings. Christopher is freaked out by an unexpected visitor. Benny’s connection to the plumber’s union comes in handy. A.J. demonstrates his business acumen. Tony ponders whether to execute a ‘sacrifice bunt.’
Gene Pontecorvo makes a final break from the mob life, while Junior’s paranoid delusions could be the end of Tony.
The family tries to cope with Tony’s hospitalization and possibly impending death, while Tony begins to hallucinate a new life parallel to his own.
While the gang begins to turn on itself, Tony finds himself at the threshold.
Tony goes home and returns to business, perhaps with a new frame of mind. Paulie receives a shock about his mother.
Johnny Sack asks for permission to get out of jail for his daughters wedding; Tony’s on the look out for personal protection.
Tony seeks guidance from overseas to solve a local problem; and decides whether a top earner deserves another chance.
Chris meets and beats the stars, while Artie turns violent after having his hospitality abused.
Vito considers starting a new life in New Hampshire, while Anthony continues his pursuit of revenge against Junior.
Paulie finds public opinion turned against him after an amusement ride accident, while Chris tries to start a new life as a husband and father.
Tony reflects on how growing up with Janice colors his attitudes now, while Vito tries to make a new life for himself in New Hampshire.
Phil takes out his revenge on Vito, while Tony grows frustrated with Anthony’s lack of ambition or work ethic.
Phil Leotardo seeks to continue a cycle of retaliation between the New York and Jersey families. Christopher wrestles with his addictions. Tony decides keeping Carmela occupied with the spec house is for the best. A.J. gets a new girlfriend.
Bobby and Janice host a wild 47th birthday bash for Tony at their Adirondacks vacation home. Tony’s actions following Johnny Sack’s arrest come back to haunt him.
Christopher’s Cleaver premieres, showing Tony how he feels about him. Johnny Sack faces a health crisis. Phil Leotardo resents his family, and himself, for being weak and downtrodden. Silvio gets caught up in New York’s power vacuum.
When Tony’s first hit is about to be unearthed, he and Paulie flee to Florida, where Tony contemplates their friendship. Junior organizes a poker game at the institution. The New York power struggle continues.
Maria Spatafore requests help from Tony for Vito, Jr. Tony’s bad luck puts a rift between he and Hesh. A.J. makes a major choice regarding his future.
The relationship between Christopher and Paulie’s falters, while A.J. grows depressed over his break-up with Blanca.
The Soprano and Lupertazzi crime families quarrel over asbestos removal. Tony deals with a problematic associate. Paulie suffers a devastating personal loss. A.J. questions his friendship with Jasons Parisi and Gervasi.
Tony attempts to repair the rift between New Jersey and New York. A.J.’s depression struggle continues. A New York associate crosses the line with Meadow.
The spectre of disloyalty among the crew hangs over Tony as Phil Leotardo decides how to handle recent issues with the Soprano crime family. A hit gone wrong comes at a huge cost. A.J.’s conquering of his depression is challenged.
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