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.
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.’
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