The fifth season of Weeds premiered on June 8, 2009 and concluded on August 31, 2009.
After Nancy informs Esteban that she's pregnant, he allows her to live but has bodyguards assigned to her and forces her to undergo a chorionic villus sampling to be sure the baby is both a boy and his. Anxious for Shane's safety, Nancy has Andy take him to her sister, Jill Price-Grey (Jennifer Jason Leigh). In the later episodes, Jill returns with Shane and Andy. Jill explains that Shane took pictures on his phone of her having sex with Andy. Meanwhile, Silas draws up a new plan to start a legal medical marijuana business, which Nancy funds. The bodyguard mysteriously disappears and Nancy panics because he was probably murdered.
Quinn's attempt to extort money for Celia's return to her friends and family fails miserably, since none of them are willing to pay any ransom. Plan B, to kill Celia and sell her organs, doesn't pan out either due to Celia's having had cancer. This leads to a dispute between Quinn and Rodolfo, and their relationship ends. Celia tries to get Rodolfo to let her stay with him but he drugs her and puts her on a bus to Texas. With nowhere else to go, she ends up squatting in Nancy's garage, where she finds the body of the missing bodyguard. The new bodyguard catches DEA agent Captain Roy Till and Nancy calls Esteban, who orders Till's murder. Andy suggests that Nancy have an abortion, after which they will flee with US$180,000 Andy discovered in Judah's old bank account, because Nancy will never be free if she has a baby with a Mexican drug lord. Nancy instead leaves a note for Andy, saying she and Shane have moved in with Esteban.
Six months later, Esteban proposes to Nancy and she accepts, but Pilar (Kate del Castillo), a powerful woman in Mexican politics, forces Esteban to break off the engagement. Cesar, Esteban's chief aide, arranges a birthing room in the house, so there will be no record of the baby's birth. Escaping Esteban's house with Andy's aid, Nancy appeals to her obstetrician, Dr. Audra Kitson (Alanis Morissette), who takes her to the hospital and delivers the baby. To protect his political career, Esteban will not sign the birth certificate. Nancy moves back in with Andy, who agrees to sign the birth certificate, hoping she'll free herself from Esteban. He also convinces Nancy to give the baby a Bris, much to Esteban's dismay.
Shane witnesses violence at the hands of Esteban's bodyguard. He continues to sell pot at school and when a teacher steals a bunch of product, Shane goes to the teacher's apartment with Isabelle and Esteban's bodyguard and kills the teacher's pet bird with a gun.
Esteban wants to see his son and comes to Nancy's door, again asking her to marry him. Simultaneously, an assassin trying to shoot Nancy misses and hits Shane in the left shoulder. When Nancy confronts him, Cesar admits to being an informant for Pilar, who ordered the hit on Nancy. The execution was not completed because Cesar could not bring himself to do it. Nancy keeps the betrayal from Esteban in exchange for getting to shoot Cesar in the arm to avenge Shane's injury. Esteban finds himself replaced as a candidate for governor, but with encouragement from Nancy, he runs as an independent.
Silas' and Doug's shop is having problems: Doug keeps eating their products, is stoned all the time, and does not keep up his work responsibilities. Moreover, the policeman in their pay begins demanding more money. However, they are raided by the police in an Internal Affairs sting against the cop, and lose all of their pot in the process. They turn to Dean to help them get it back. Meanwhile Celia gets a job as a home sales representative for a cosmetics company. Unable to sell the makeup, Celia gets Dean to give her the pot and starts selling it packaged with the cosmetics.
Doug finds out that Celia stole their pot and he and Dean plot revenge. Shane eschews painkillers for his arm wound, saying he prefers the pain. Instead, he begins sneaking alcohol. Silas refuses to go abroad to study, expressing worry that Shane is going to "crack up".
Andy begins a relationship with Dr. Audra Kitson. The family moves into Esteban's house, and Nancy and Esteban get married at home. Nancy visits Guillermo in prison to arrange for the assassination of Pilar in exchange for Guillermo's extradition to Mexico. Esteban becomes the front-runner for governor despite Pilar's rejection, but is arrested for suspicion of conspiracy, racketeering and tax evasion. When Nancy and Cesar attempt to retrieve Esteban from jail, they learn via national television that Esteban has been already released and is again running for governor- but on Pilar's platform. Pilar arranged for his arrest, and is blackmailing him into becoming her political puppet. Pilar confronts Nancy and tells her that she and Esteban must do everything Pilar dictates. Andy announces that he is going to propose to Audra, with his mother's ring, previously given to Nancy by her late husband Judah. Nancy is upset and initially refuses to give Andy the ring, but later relents.
Thereafter, Celia gathers Doug, Dean, Sanjay, Ignacio, and Isabelle—teaming them up to sell marijuana in a deliberate echo of season one when Nancy did the same. Pilar discreetly, but forcibly, corners Nancy at a fund-raising party. As they walk by a pool on the outside deck, Pilar reveals to Nancy that she has been aware of her actions. Pilar then suggests that the apparently accidental deaths of Shane and Silas, would generate a sympathy vote for Esteban. Nancy threatens to kill Pilar if she endangers Nancy's children. At that moment, Pilar is whacked in the head by an unseen third party and ends up floating face down in the pool, bleeding profusely from the head. Shane appears next to Nancy, holding a croquet mallet.
- Wonderful Wonderful
- Machetes Up Top
- Super Lucky Happy
- Van Nuys
- A Modest Proposal
- Where the Sidewalk Ends
- A Distinctive Horn
- Suck 'n' Spit
- Perro Insano
- Ducks and Tigers
- All About My Mom
- Mary-Louise Parker as Nancy Botwin
- Elizabeth Perkins as Celia Hodes
- Hunter Parrish as Silas Botwin
- Alexander Gould as Shane Botwin
- Allie Grant as Isabelle Hodes
- Justin Kirk as Andy Botwin
- Kevin Nealon as Doug Wilson
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