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- After a visit with his sons, Schillinger realizes he needs to get paroled. He convinces McManus to let him return to Em City with the condition that he leaves Beecher alone. Beecher comes out of the hole hell-bent on making sure Schillinger doesn't get paroled. McManus gets wind of Wittlesey and Ross' contraband operation and orders her to shut it down. Ross makes it very clear to her that this will not happen. The Muslims meet and discuss how the riot will begin. However, two rednecks beat them to it by fighting over a game of checkers. This causes all the inmates to get involved and they quickly overpower the COs who are trying to break it up. Said orders the Muslims to get out and seize control. Said pulls out the gun he acquired from a rookie CO and fires a shot into the air, causing Em City to quiet down. Said meets with Ross, Adebisi, O'Reily and Alvarez to discuss strategy and demands. Said agrees to let O'Reily, Ross and Adebisi control the main gate and Alvarez will control the hostages. Dobbins was seriously injured during the initial uprising and Hill convinces Vayhue to step up and help. Vayhue and Dobbins leave Em City only to be beaten up by SORT. The hostages require medical attention, so Alvarez and Said vote in favor of a doctor. However, Adedisi, Ross and O'Reily vote no. Governor Devlin orders the National Guard to surround the prison and take it back, but Glynn and McManus think they should see the demands first. McManus volunteers, to Devlin's disgust, to enter Em City to deliver food and check on the hostages. He tries to get COs Armstrong, Mineo and Wittlesey free in exchange for himself. He gets Armstrong and Mineo released, due to their injuries but Wittlesey has to stay. After reading the demands, Glynn realizes that the prisoners are being quite reasonable, however Devlin orders the National Guard and SORT to re-take Em City anyway. Meanwhile Ross' men and Adebisi's are constantly fighting, so Said tells O'Reily to switch Ross' men with Alvarez's at the front gate. A short tie later, Adebisi's men start to fiend due to the depletion of heroin, resulting in a major skirmish. Just as that situation is resolved and the Homeboys are tied up, the lights go out. Said realizes the situation and orders Ross to bring out the hostages as a front line of defense. Soon tear gas is thrown into Em City, then a tractor breaks through the barricade and gunfire rings out in Em City.
- L.T. and Vicki "Chad Morgan" pose as a couple in order to research and write a newspaper article on interracial dating. Margot struggles with her mother's independence. Russell and Claire disagree over whether he should become a police officer.
- Buttle meets a beautiful girl, Lisa, who shares his love of Shakespeare. Back at Winslow High, Senate learns that Juan Figgis' mother has been convicted on drug charges and is going to prison. Meanwhile, Lipschultz collapses in class and is rushed to the hospital. Buttle breaks up with Louisa when he realizes he is in love with Lisa, only to find out she is not a 20-year-old Harvard student, but an 18-year-old student at Winslow High.
- Coach Riley has a serious crush on Marilyn Sudor but is nervous about asking her out due to their racial differences. Meanwhile, Harper is concerned about the cheer-leading squad. They have been rehearsing for an important competition, but their new routine is extremely sexual. The choreographer argues that it's impossible to tone down the program, so Harper cancels the meet. Regardless of the consequences, Lisa and Buttle continue to tempt fate and continue their heated affair, and in an effort to help his kids discuss their feelings, Senate forms a "Suicide Club," which outrages parents and faculty alike.
- Harry advises Tyronn to leave town when he is shot at. Harvey sends Scott on a two-hour drive for a non-existing conducting opportunity. A student accuses the cheer-leading teacher, Tina, of touching her in inappropriate ways. Tina is suspended with pay pending the investigation. Lauren inadvertently hinders Tina by saying that she once hit on her. The girl's parents reveal that their daughter is a pathological liar who has made these accusations before and has even accused Steven of touching her. Tina's suspension is lifted. She angrily states that if it had been Lauren, she wouldn't have been suspended. Steven retorts that Lauren doesn't coach her students to do lap-dances.
- It's Thanksgiving week, but no one seems particularly grateful. Guber, for example, is still upset over his onstage serenade at the charity show. Football player Jason Harrelson broke bully Malcolm White's arm during a fight in the hall. Buttle is starring in yet another Sheryl Holt original online humiliation cartoon. Last, but not least, Lauren discovered a senior sex posse which awards senior guys points for sex. In response to the sex posse scandal, Principal Harper organizes a sophomore assembly to preach the benefits of chastity. The teachers draw straws, and Lipschultz is chosen to head up the event. Later at the assembly, Lipschultz' boring speech turns shocking when he confesses to catching his beloved late wife in bed with another man.
- Rehearsals are in full swing for the annual charity show. Marilyn is dismayed to learn that the main skit the students have prepared is a spoof of the Winslow High faculty - complete with a gun-toting Senate and Buttle stuck inside a donkey! Elsewhere on campus, Lauren enters a stairwell and catches two student body presidential candidates engaged in a sex act. Lauren confronts the students - Peter and Susan - who deny any wrongdoing. However, when Peter later drops out of the election, it becomes clear that Susan's sexual favor was a motivating factor. On top of all this, Lauren must also deal with John LeBlonde. John's an excellent student on the recently suspended soccer team and needs Harper's approval to apply for a prestigious academic award.
- Lauren finds Harry hasn't told his friend about her. Six teachers resign and Marla must teach a class she doesn't know how to. Scott wins a contest to be a guest conductor with the Boston Pops and asks Marilyn out when she is too nice to him. Steven and Harry look for a missing teacher, only to find him passed out drunk in his home. Apparently, he deserted his class the previous November, leaving Lisa Grier to teach and nobody noticed or cared. Steven decides to let Lisa continue to teach, touching off a firestorm by faculty and parents alike.
- The first day back at school has barely begun when the police show up looking for a murder suspect. A botched robbery has gone down a few blocks away and the panicked assailant, wearing a Winslow High Letterman's jacket, shot and killed a man before heading towards school grounds.
- While heading to work, Lauren's car breaks downs. She gets so frustrated with it that she starts jumping up and down on it and smashing the windows with a baseball bat. Suddenly, an old student of hers appears named Daniel Evans who thanks her for changing his life. He shows her a history text book he has written and she is very impressed. He asks her out for a drink, and she immediately says yes. After, they head to her place and have a night of passion. The next day she tells Marilyn, who finds it a little immoral. Lauren cannot get past how great the sex was. Lauren admits she finds it a total turn on when Daniel calls her Ms. Davis.
- Another school year is off to a booming start at Winslow High School - an urban high school outside of Boston. Principal Steven Harper spends his days putting out fires, defending his faculty and just trying to keep it together. Lauren Davis, the idealistic head of the social studies department, and Harry Senate, a geology teacher with buried secrets, are embroiled in controversy for failing the star running back before a huge game with the cross-town rivals. But they both have bigger personal problems. Lauren has been asked out on a date by the icy vice principal and Harry has been put on probation for wielding a gun in one of his classes. When he's not dodging the star running back's lawyer or pulling a bully off the class geek, Principal Harper is trying to calm Ms. Hendricks. She left her class after scrawling "Gone to kill myself, hope you're happy" on the chalkboard. Meanwhile, English teacher Milton Buttle has become the star attraction on student Sheryl Holt's website. His unflattering, animated portrayal has made Buttle the butt of everyone's jokes. And let's not forget dear old Mr. Lipschultz. The 80-year-old American history teacher kicked popular Dana Poole out of class for not wearing a bra.
- Life seems to be one big lawsuit for Principal Harper. First, Mrs. Walsh, who was fired for spanking her students, sues for wrongful termination. Then, after Harper suspends Sheryl Holt for offensive content on her website, she sues to get the suspension overturned. Lauren gets knocked out by a launched breast implant. While Marylin counsels the girl on her self-image, Lauren decides to let the boyfriend off the hook. In court, Lipschultz's testimony - on both the Holt and Walsh cases - is disastrous and results in two losses for the school.
- A student's mother complains about bus fumes to Steven. The tape of Lauren showering ends up on Sheryl Holt's website. Harry gets in trouble for knowing Tyronn was a murderer. Scott becomes Lisa Grier's co-teacher for her Shakespeare class.
- A popular and beloved teacher, Mr. McMahon, has a heart attack and dies at school. A close friend of the deceased, Principal Harper overcomes his own grief to help his students cope with the loss. To make matters worse, it appears that McMahon had been having an affair with a female senior, Karen Fitzgerald. While Harper struggles to deal with the incident's aftermath and maintain status quo, the students and faculty begin to fall apart. A defiant pupil, Webster, spits on Lauren and she vows to have him expelled. The case becomes more complex, however, when Harper learns that Webster was close to Mr. McMahon and is extremely upset over his death.
- Sheryl Holt breaks the news about Milton and Lisa's secret affair on her website. Suspicious, Harper confronts Buttle about his sexual involvement, but Milton disavows any wrongdoing, claiming that he and Lisa have started a "Shakespeare Club." However, Riley has his hands full with another explosive situation - an anonymous bully has severely beaten three male students. Meanwhile, Marilyn suspects that a girl in her class is a victim of incest when the student writes a "fictional" essay about her father molesting her. In the middle of this crisis, Guber asks Lipschultz to resign after accusing him of being a racist.
- When Coach Riley is fired for withholding information about Buttle's affair, he hires the best attorneys in Boston - Ellenor Frutt and Jimmy Berluti. Ellenor immediately begins subpoenaing witnesses, sending a message to Winslow High that she means business. Meanwhile, Lauren discovers that Harry had dated another co-worker, Jenna, before her. Disturbed that Harry would have a relationship with a woman Lauren deems unsavory, she becomes concerned about her own relationship with Senate. In court, the reputations of the entire faculty at Winslow are smeared, but the closing argument (given by Steven Harper himself) convinces the judge to uphold the termination. Kevin angrily tells Harper that his decision demonstrated the he cared less about the students than protecting his own authority. The episode ends with Kevin and Milton saying goodbye to the faculty, excluding Harper and Guber.
- Principal Harper's job is in jeopardy and an impending school board meeting has him on edge. Still, he can't help but get involved when Anthony Ward is found hanging upside down from the roof. It turns out the entire soccer team has ganged up on little Anthony since he thwarted their attempts to download answers for a test. Harper's decision to suspend the entire team, and thereby forfeit the soccer season, only adds fuel to Superintendent Marla Shinn's fire. Meanwhile, Harry Senate confesses to kissing Dana Poole and explains her blackmail scheme. Guber sends a shocked Dana to Bob "Big Boy" Lick for counseling but Harper does not suspend Senate. Coach Riley, on the other hand, is dealing with a football team who has marked one of their teammates as gay and will not shower with him. Plus, Lauren is left to defend herself when Superintendent Shinn questions the topic of cannibalism being taught in Lauren's classroom. At the school board meeting, things come to a head when all of the faculty's - and Principal Harper's - indiscretions are exposed. Surprisingly, an impassioned speech by Marla Hendricks puts everything into perspective, and even manages to silence Superintendent Shinn. At least, temporarily.
- As Senate approaches the school grounds, he saves a student from being attacked by gang members. After numerous attempts, Harry finally manages to get the boy to reveal that he is a member of the Crips. Meanwhile, Harper grows even more suspicious about Lisa and Buttle's deepening friendship, so Guber takes the reins and alerts Lisa's parents about their daughter's rumored affair. In the midst of these crises, Lauren has her hands full trying to help an overweight female wrestler, Christine, cope with the loss of her boyfriend. After winning an important wrestling match, Christine addresses the audience and asks them to stop calling her "The Blob", even when it's supportive. They respond by chanting her name instead. Lisa Grier's father goes to Buttle's home and catches them about to have sex. The next morning, Guber gives Buttle a choice: Voluntarily resign or be fired in such a manner as he'll never teach again. Buttle resigns and is ordered to leave by Guber. Harper also rebuffs Buttle. Kevin Riley talk to Guber and tries to mitigate Buttle's actions and ends up getting fired immediately for not disclosing the affair sooner.
- Steven's remarks prevent Scott from getting a job as a headmaster. Lauren finds out Daniel is stalking her. Marla worries when a convicted sex offender asks a younger girl to the senior prom. Marilyn suspects Jeremy has done something to his mother. Anthony Ward is accused of threatening a girl who turned him down for the prom, prompting the superintendent to transfer him to another school.
- Lauren gets a gun to protect herself from Daniel, only to get a two-month suspension for pulling it on school grounds. Jeremy won't tell Marilyn what happened to his mother. Daniel's parents reveal that their son has serious psychological problems and that his History textbook was plagiarized. Marla gives Winslow High's first student to get accepted to Harvard an F. In order to bolster Winslow's reputation and prevent a lawsuit from the parents, Harper convinces Lipschultz to re-evaluate Marla's F Grade and doctor it to a D. At prom, Kevin Jackson gives a speech bemoaning the lack of heroes in their generation but praises the faculty for being real heroes. Guber gets a special award from the students. Jeremy Peter's mother is shown locked in the basement, tied to a chair with a gag over her mouth.
- Last week's bra protest has resulted in school unity. All the girls have decided to go bra-less in a show of solidarity with Dana Poole. The superintendent is breathing down Harper's neck because Lauren has rallied a few of the other teachers and they all refuse to get fingerprinted. Also, Marla, who is supposed to be on medical leave, has shown up for work, and Lipschultz, the man behind the bra debacle, has shown up on Sheryl Holt's infamous website - in a bra and panties! Meanwhile, Vice Principal Guber tries to regain control by meeting with Dana Poole. He suspects that she's high, so he wants a urine sample. She protests and bolts straight to Harry.
- L.T. is assaulted by a schizophrenic man (Billy Dee Williams), who also steals his camera. L.T. then discovers the man was once a great photographer. Meanwhile, Dinah is worried she won't be asked to the spring dance, and Russell sees some police action.
- Russell risks losing a wealthy volunteer at the teen shelter, when he tells her to stop throwing money around and explains how the money could really help the kids. Meanwhile, Dinah and boyfriend Michael (Jesse Petrick) plan a weekend alone.
- This episode, better known as "Jimmy Kimmel Sucks" has Matt Damon kidnapping Jimmy and hijacking his show, where he proceeds to fire Guillermo and Cleto, replacing them with Andy Garcia and Sheryl Crow. Then he hires Robin Williams to do the opening monologue, gets kudos and congratulations from a number of celebrities and Jimmy's parents, who adopt Matt as "the son they really wanted". We are then shown Jimmy's attempts to audition, horribly, for every role Matt ever played. Many big-name celebrities make guest appearances on this show, including Jimmy's ex-girlfriend. The show ends with Jimmy getting bumped by Matt.
- Claire worries that Josh's involvement with Bobbie could be a problem. Margot "Ashleigh Norman" is hit by a car and her mother's "Christine Healy" agoraphobia prevents her from visiting Margot in the hospital. Meanwhile, L.T.'s award-winning play is disqualified for its subject matter.