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- New Jersey mob boss Tony Soprano deals with personal and professional issues in his home and business life that affect his mental state, leading him to seek professional psychiatric counseling.
- A free-thinking art professor teaches conservative 1950s Wellesley girls to question their traditional social roles.
- Mike Flaherty, the Deputy Mayor of New York City, and his team of half-wits must constantly save the Mayor from embarrassment and the media. Mike is later succeeded by Charlie Crawford.
- The secret to a Stepford wife lies behind the doors of the Men's Association.
- A single mother, with dreams of becoming a writer, has a son at the age of 15 in 1965, and goes through a failed marriage with the drug-addicted father.
- A down-and-out writer sells his soul to the Devil in exchange for fame and fortune.
- Mobster Paul Vitti is released into Dr. Ben Sobol's care, where only more chaos ensues.
- An idealistic prep school teacher attempts to redeem an incorrigible student.
- The film follows a rebellious teenager on leave from the Marines who falls in love with a female musician. The relationship is threatened when she develops a mental illness...
- Tony realizes that he must take care of family messes himself in order to keep the peace within his own clan.
- 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.
- Gloria grows increasingly demanding until Tony realizes who she is, and Jackie Jr. ends up in very serious trouble when Chris realizes who he is.
- Tony and Carmela try a therapy session together and ends it angrily. Artie, meanwhile, tries to move in on Adriana. Bobby 'Bacala' Sr. comes out of retirement for one last job much to his son's objection after it ends tragically.
- Ralphie issues his final decision on the fate of Jackie Jr., Anthony Jr., faces military school after getting expelled, Paulie and Ralphie have a financial conflict while the FBI assigns Adriana a new "friend."
- 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.
- Tony continues putting the squeeze on David, while Richie discusses the possibility with Junior of removing some competition while 'Big Pussy' Bonpensiero continues to be an informant.
- Tony's dreams seem to tell him where his life is headed, but he still feels as though he's out of control.
- Columbus Day ignites tensions between Italians and Native Americans, and Bobby receives devastating news about his wife.
- 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.
- Tony, Paulie and Chris travel to Naples to conduct a business deal, while Pussy becomes more stressed over trying to balance his secret lives.
- Anthony continues to cause problems at home, while Pussy's divided loyalties cause him greater anguish.
- Carmela and Furio grow too close for safety, while Paulie discovers that he's not as big a fish as he thought he was.
- 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.
- 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.
- 1999–200758mTV-MA8.2 (6.7K)TV EpisodeChris puts a ghost from his past to rest, while Carmela grows uneasy about her future.