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1-50 of 91
- Rebellion by some of the lower soldiers ends in bloodshed, while Carmela starts intimidating her neighbors to help Meadow's chances at Georgetown.
- Tony encourages an unwanted son-in-law to divorce, Carmela learns another secret of Tony's, Meadow experiments with speed to study for the SATs, and Chris and Brendan find out the price of disrespecting Junior.
- 1999–200746mTV-MA8.5 (6.8K)TV EpisodeTony starts having flashbacks about Pussy's betrayal, and then later discovers that Jackie Jr. has been failing in his responsibilities.
- Tony's dreams seem to tell him where his life is headed, but he still feels as though he's out of control.
- The stress Tony is going through begins to take its toll, and the hit Junior has ordered doesn't help.
- 1999–200749mTV-MA8.6 (8.5K)TV EpisodeThe FBI begins closing in on the DiMeo family. Tony and Carmela are angry over all the attention Italians get from the authorities, while Chris fumes that he's not getting enough attention.
- Noah and Meadow's relationship is disrupted by her roommate, while Ralphie starts getting rough with one of the strippers from the Bada Bing causing Tony to intervene and questionably violating one of the mafia codes of conduct.
- Tony is getting fed up with his mother. Brendan Filone acts against Tony's wishes. Salvatore and Paulie try to track down A.J.'s teacher's stolen car.
- 1999–200750mTV-MA8.2 (7.7K)TV EpisodePussy returns after months in hiding, Chris starts a boiler room stock operation, and Tony's long-lost sister shows up on the doorstep.
- The FBI has trouble finding a new informant, so they attempt to bug the Soprano home.
- Tony tries to balance Junior against the other capos, while Carmela reasserts herself as the woman in Tony's life.
- Carmela and Tony go away to Bobby's cabin upstate New York for Tony's birthday up where a fight emerges between Tony and Bobby over Janice. Meanwhile A.J. is throwing a party at the Soprano home.
- Junior leaves prison due to ill health and placed under house arrest, while Livia's health also declines. Pussy begins talking with someone interested in learning more about Tony.
- Tony's old school friend digs himself into trouble with his gambling, while Tony's family problems only continue to grow.
- Richie Aprile gets out after ten years in prison and starts reasserting his authority while unaware of the changes made in the crime family's archetype. Meadow gets in trouble after a party gets out of hand.
- Paulie and Silvio get promoted, Furio gets welcomed, Pussy gets pushed aside, and Chris gets frustrated with his Hollywood aspirations while Janice and Richie become romantically involved much to Tony's disapproval.
- The capos discuss what to do about the local soccer coach, while Junior's mouth causes him some embarrassment.
- Chris and cousin Tony do some digging to make sure old secrets stay buried, while Janice puts her marriage in jeopardy with her fierce temper.
- Anthony has disciplinary problems at school, prompting Tony to recount memories of his childhood with Dr. Melfi.
- A car crash puts Tony and Adriana in a compromising position, and Cousin Tony tries to keep Chris from getting the wrong impression and the wrong information.
- Tony hits an unlucky series of gambling losses, causing tension with both Carmela and Hesh. AJ and Blanca decide to make major changes in their relationship.
- Tony tries to branch out into legitimate investments, while Chris and Adriana decide to try their hands at music production.
- Feech makes a pain of himself by trying to return to his past glory. Carmela tries to work with Anthony's teacher to rein in their out-of-control son.
- Tony, Paulie and Chris travel to Naples to conduct a business deal, while Pussy becomes more stressed over trying to balance his secret lives.
- Dr. Melfi is attacked and when the authorities lets her down, she considers asking Tony to help. Janice has a dispute with Svetlana. Ralphie gets passed over for a promotion and Jackie Jr. gets involved in the family's crime activities.
- Gene Pontecorvo makes a final break from the mob life, while Junior's paranoid delusions could be the end of Tony.
- 1999–200753mTV-MA8.8 (6.6K)TV EpisodeJohnny Sack is granted permission to attend his daughter's wedding. Tony improves his personal security and Vito's secret double life is exposed.
- In the midst of suspicions that he killed Ralph, Tony tries to intervene to get Chris clean and sober.
- Adriana learns that life is not like TV shows, while Tony discovers that a former girlfriend has moved on, along with Ralphie and others they scam the Department of Housing and Urban Development.
- The allegiance of those closest to Tony is put to the test. A case of mistaken identity has serious ramifications.
- Tensions rise between Tony and Ralphie until circumstances demand that they resolve their differences. Meadow gets involved with Jackie's son, and ends up in trouble.
- The family tries to cope with Tony's hospitalization and deteriorating condition, while Tony begins to hallucinate a new life parallel to his own.
- An uncomfortable party leads Tony and Carmela to a partial reconciliation, while cousin Tony gets an offer he decides not to refuse.
- Brendan's death leaves Chris fearing for his life, and Anthony's discovery of what his father really does leaves him confused.
- Paulie finds public opinion turned against him after an amusement ride accident. Christopher tries to start a new life as a husband and father.
- Some of the old guards are released from prison and want to get back in the action. Chris and Paulie are at each other's throats over matters of money and respect, and Tony decides to tell Dr. Melfi what's really on his mind.
- 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.
- Columbus Day ignites tensions between Italians and Native Americans, and Bobby receives devastating news about his wife.
- Tony feels depressed over the negative impact he has on people who don't deserve it, while Carmela tries to set up Furio with a friend, AJ is uncomfortable with his girlfriend's wealth, Artie attempts a new business venture.
- Tony learns about his father through the man's mistress, while Chris' friend learns that there are habits more harmful to your health than heroin. Junior becomes obsessed in attending funerals but that leads to a change in his mood.
- Vito considers starting a new life in New Hampshire, while Anthony Jr. looking for a purpose and finds it when he continues his pursuit of revenge against Junior.
- Christopher and Carmine travel to Hollywood to take the next step in making their movie but quickly realize they're out of their depth. Artie feuds with Benny after his restaurant falls prey to one of Tony's scams.
- Ralph buys a racehorse, but Tony ends up more attached to it than Ralphie is. Carmela starts trying to invest in her future.
- Carmela has another furtive romance collapse, while Tony B. throws away a chance to turn his life around.
- With Carmine's passing and Feech's arrival, turf wars are breaking out around New Jersey. Junior's mental health, meanwhile, starts to decline.
- Johnny Sack finds out he only has 3 months to live. Meanwhile, 'Cleaver' premieres and is a hit, while Carmela has mixed emotions about it, saying too much of it is based on Tony.
- Tony travels to Las Vegas after a tragedy occurs.
- Tony fails to reason with Phil as more problems increase with Anthony Jr as his depression worsens.
- Tony realizes that he must take care of family messes himself in order to keep the peace within his own clan.
- Chris awakens from his coma with a message from the afterlife for Tony and Paulie. Carmela, meanwhile, wants Tony to get a "cut", specifically a vasectomy.