After Lainey Lewis's music career doesn't take off, she takes a job as the new music teacher at William Penn Academy, but struggles adjusting to being on the other side of a teacher's desk. She finds herself tested when she clashes with Principal Glascott's niece, but eventually finds a way to inspire her. Meanwhile, Coach Mellor struggles to adapt to the changes in sports in the 1990s as Matt, his star basketball player, wants to be like Michael Jordan. Mellor challenges Matt to a game of Horse trying to get through to him and later inspires him to try out for football, leading to his eventual NFL career.

Featured Songs: "Today" by The Smashing Pumpkins, "Good Vibrations" by Marky Mark and the Funky Bunch

Based on the movie She's All That. After Lainey sees the movie more than 18 times, she's inspired to give one of the students a makeover. Elsewhere, Principal Glascott and Coach Mellor both became smitten with the drama teacher. Meanwhile, CB makes a bet that he can turn Lainey into a better teacher.

Featured Song: "Kiss Me" by Sixpence None the Richer

Lainey tries to convince a controlling parent (Rob Riggle) to allow his son to perform in the bell chorus but meets resistance from Glascott when he informs her the parent is donating a computer lab to the school. In an effort to teach Glascott to stand up to domineering parents, Lainey recruits the greatest domineering parent of them all, Beverly Goldberg. Meanwhile, when Coach Mellor confiscates everyone's Tamagotchi and then starts playing with them, he becomes motivated to become a real parent and recruits a reluctant CB to help him.

Featured Song: "Wonderwall" by Oasis

With Ms. Flemming burned out from coaching the school's mathlete team, perennial losers in the annual Math Olympics, Principal Glascott turns to Coach Mellor to motivate the team. Meanwhile, CB doesn't know how to handle a sarcastic bully (Thomas Barbusca) in his class, so he seeks advice from Lainey.

Featured Song: "These Are Days" by 10,000 Maniacs

Frustrated with the public domain options for the school musical, Lainey spends her own money so her class can perform Rent. Coach Mellor gets mad when one of his star football players defects to take a lead role in the play, and he intentionally schedules a pep rally in the auditorium the same day as the performance. Elsewhere, CB is recruited to teach sex ed, but becomes uncomfortable with the questions the students ask.

Earl Ball asks Lainey to teach an easy class for the school's top athletes but Coach Mellor, in an attempt to push his students to achieve their full potential, challenges her to actually teach the jocks. Meanwhile, Principal Glascott is worried that his niece will not get into a good college and resorts to bribery, first to get his niece to run for class president and then, when she actually shows genuine interest, to get her opponent to drop out of the race.

Featured Songs: "All Star" by Smash Mouth, "Pump Up the Jam" by Technotronic

Lainey and CB struggle to get the student body to conform to the school's dress code after two students come to school with their clothes worn backwards. They are further dismayed when the two students state their intentions to perform a Kris Kross song at the school talent show. Meanwhile, Principal Glascott seeks Coach Mellor's guidance on how to deal with the demands of his job.

Lainey reunites with Erica Goldberg in time for the 10 year reunion at William Penn Academy. The pair think their lives have been mundane and decide to emulate a ploy similar to that of Romy & Michelle's High School Reunion to impress their former classmates. The ploy backfires when their old classmates see Lainey's picture in the hall, figuring out she is on the school staff. Meanwhile, Coach Mellor is dismayed that his protege, Ruben Amaro, Jr. does not reciprocate the same sentiment and considers Principal Glascott his greatest influence during his time at the school.

C.B. and Coach Mellor get into a debate about Star Wars, after Mellor is invited to watch Episode I: The Phantom Menace by the sci-fi club. When Mellor shares his thoughts on the movie, which causes the club to disband, C.B. retaliates by giving his honest thoughts about baseball, which Mellor takes to heart. Meanwhile, Principal Glascott does not think he can trust his niece, Felicia and her intentions on getting her driver's license, and asks Lainey for help.

Featured Song: "Ordinary World" by Duran Duran

When two boys get in a fight, Glascott and CB are at odds over how to resolve the conflict. Meanwhile, Lainey takes over as cheerleading coach and, with surprising support from Coach Mellor, has to convince the football team that cheerleaders are athletes, too.

Principal Glascott and Coach Mellor engage in a debate when Glascott opts to replace William Penn's longtime mascot with a less-intimidating cloud.

Featured Songs: "Push" by Matchbox Twenty, "Sirius" by The Alan Parsons Project

When a concert that music scouts attend and the school talent show fall on the same night, Lainey must choose between being a teacher and her rock star dreams. Ms. Cinoman tries to push CB into telling Lainey that he likes her. Meanwhile, Principal Glascott uses the task of building the school website to promote teamwork among his staff.

Featured Song: "Ironic" by Alanis Morissette

Cameo Interview: Interviewed by her acting counterpart, Susan Cinoman

Having not yet professed his feelings for Lainey, CB is distraught when Barry Goldberg, now a radiologist, shows up at the school and asks Lainey to move with him to Michigan. Elsewhere, Glascott's mishandling of the senior prank in full view of a school board auditor has him fearing he will have to step down as principal, but he gets support from a surprising source.

Featured Song: "I'm Gonna Be (500 Miles)" by The Proclaimers

Inspired by the film Dangerous Minds, Lainey thinks she can affect change in the lives of her students, but giving them the number to her "portable" cellular phone starts to backfire. Having seen Lainey complete a tumultuous first year under his tutelege, Mellor looks for another young teacher to mentor and targets Coop. Several teachers, especially C.B., are taken aback by new biology teacher Wilma Howell and her tough methods of instruction.

While talking with Lainey, Coach Mellor professes that he and Miss Cinoman are in a Ross-and-Rachel type relationship and just "on a break", even though it's been seven years since they last dated. Lainey learns that Miss Cinoman clearly thinks it's over, so she encourages Mellor to try speed dating. Elsewhere, Principal Glascott has to deal with increasing angry outbursts and demeaning behavior from Dr. Ness, the school librarian. He wants to take an approach of compassion and encouragement, but Wilma insists he has to be tough and fire Ness.

After wimpy kid Toby Murphy watches the film Rudy in C.B.'s class, he tells Coach Mellor that he wants a shot to play on the football team. Mellor is hesitant, but after watching the movie himself, he has Toby suit up and runs a "fake Rudy" play in practice to make the kid feel good. All seems to be well until Julie, Toby's aunt and a woman Mellor is trying to impress, asks if Toby will be playing in the team's final home game. Meanwhile, Erica Goldberg tells Lainey she is too busy to attend a Boyz II Men concert with her, so Lainey tries to befriend Wilma. Boyz II Men (Nathan Morris, Shawn Stockman, Wanya Morris) performs a spoof of their hit Motownphilly.^[24]

After seeing Felicia's prowess on the soccer field, Mellor and Glascott recruit her to be the kicker for the football team. However, when a boy Felicia likes starts seeing her as "one of the guys", she wants to quit. Elsewhere, Earl Ball reluctantly allows Lainey to be a chaperone for a class ski trip despite her history as a troublemaker on such trips. Co-chaperone C.B. uses the opportunity to try and spend some alone time with Lainey, but is constantly interrupted by Tom Scott's requests for romantic advice.

A flu outbreak has Glascott scrambling for substitute teachers, and Lainey is passed over because she hasn't met the state's "minimum competency" requirements to teach academic classes. She learns the fastest route to getting certified is to take a night class at a community college, but backpedals after learning that C.B. is the instructor. Meanwhile, Mellor contracts the flu and has to miss a wrestling tournament that awards the coveted Jenkin Cup. Glascott steps in as coach, and his appeal to the wrestlers' emotions surprisingly results in victory.

Mellor learns that Toby's Aunt Julie loves the movie Forrest Gump, so he plans to play Forrest for Halloween to Julie's Jenny. However, Mellor is soon heartbroken when Julie tells him she is being made Toby's legal guardian, as Glascott's rules prohibit teachers from dating a parent of any William Penn student. Elsewhere, the middle schoolers plan to scare the elementary students as they do their annual costume parade through the Academy, because that's what happened to them a few years ago, but C.B. and Lainey try to convince them otherwise.

When Earl Ball pushes Lainey to produce The Lion King for the annual school musical, she feels overwhelming pressure to top the success of Rent from last year. C.B. and Wilma offer their assistance, but it doesn't lessen Lainey's stress a bit. Elsewhere, Coach Mellor sees the athletic records he set as a student falling off the wall one by one, so he resorts to sabotage to keep the one record that remains: his 14-foot, 7-inch pole vault.

Despite a disinterested faculty, C.B. prepares a number of food items for his annual Friendsgiving party, which leads to his new home burning down. Realizing how much they've hurt their fellow teacher, the faculty rallies to support him and help replace his lost items. Meanwhile, Mellor and the equally competitive Wilma face off as coaches for the annual student Thanksgiving flag football game. Mellor tries to stack the deck by bringing in successful William Penn alumni to play for his team, leading to Wilma calling on Rick's brother, Nick (Bill Goldberg).

Featured Song: "I'll Stand by You" by The Pretenders

Attempting to bond with Toby, Mellor tries to learn all he can from C.B. about the Pokémon craze so he can support Toby at his Pokémon card tournaments. However, Mellor's competitive nature soon takes over. Meanwhile, Lainey takes a second job at a video rental store, but soon finds that students won't rent anything with her at the counter. To win them over, she agrees to secretly replace their videotapes with R-rated movies, but this soon backfires. Also, Lainey learns that Weasel likes singing, and gets him to overcome his fear of backlash from the jocks to perform a song on stage.

Upon learning that Lainey is desperate to get her hands on a Patti the Platypus Beanie Baby, C.B. becomes intent on locating one and buying it for her to prove how much she means to him. After one failed attempt, he enlists Mellor's help, only to find Barry Goldberg in line looking for the same thing. Meanwhile, Glascott is determined to have a more inclusive holiday concert and insists that his niece Felicia take the lead in doing a song about Kwanzaa. Felicia is not thrilled with the idea, and fights back by having multiple students try to work in something from nearly every holiday tradition around the globe.

In order to dispel the myth among her students that she's scary and mean, Wilma encourages Ronnie and other male students to form a boy band. Unfortunately their first music video turns out so bad, even they can't stand it. Meanwhile, Coach Mellor tries to convince Principal Glascott to hire Toby's Aunt Julie (and his girlfriend) as the new school nurse, in spite of his hesitation over having couples working together.

Students and teachers alike (especially Lainey) are being targeted left and right for violating the William Penn Academy dress code. Meanwhile, Coach Mellor fears his relationship with Nurse Julie is threatened when he finds out she's not a sports fan.

As the blockbuster movie Titanic is all the rage at William Penn, Lainey urges C.B. to go see it with her. C.B. resists at first, but eventually agrees. Upset about Lainey comparing the love story between Jack and Rose to herself and Barry, C.B. reacts by pointing out flaws in the film. He further announces that it's time to "move on" and move out of Lainey's place. Lainey eventually catches on that she is the girl C.B. can't get over. Meanwhile, Mellor is despondent after his star quarterback suffers an injury on the eve of the longstanding grudge match with Germantown. When it becomes obvious that William Penn can't win, Mellor takes advice from Glascott on how to lose gracefully.

Glascott decides to recreate the game show Singled Out for a school charity event, with himself as host and Lainey as the contestant. Lainey is certain that Barry Goldberg will emerge as her perfect match. However, after all other men are weeded out, both Barry and C.B. continue to correctly answer every question about Lainey, resulting in a tie. Meanwhile, Glascott tries to convince Felicia that she's both beautiful and accomplished after learning she feels too body-conscious to participate in swim class.

Upon realizing that Lainey is still committed to make things work with Barry, CB finds it difficult to move on and leave his feelings behind, but he gets support from Wilma and Mellor. Meanwhile, Lainey mentors Claudia, a student who is having strained relations with her mother, which forces Lainey to confront her own past family issues.

Lainey gets jealous upon hearing Wilma sing much better than she does, and acts out to prevent losing her status as the school's rock star. Meanwhile, Coach Mellor and Nurse Julie have differing views on how Toby should handle being targeted by a bully.

When Wilma and Mellor put the school's new community vegetable garden right in Earl Ball's board member parking spot, Ball decides to take it out on Glascott, who is reluctant to challenge his predecessor. Meanwhile, CB sacrifices being a good teacher for Weasel in order to hang with his cool dad Greg (Hayes MacArthur), who can get CB tickets to events at The Spectrum.

Coach Mellor convinces Lainey to take a drive to Altoona and make peace with her estranged mother, Deb (Megyn Price). Lainey learns that Deb has gotten sober, but is soon disappointed when she realizes her mom has been sober for five years and never tried to make contact. At school, Wilma is excited to have the talented Caroline (Olivia Taylor Cohen) join the robotics team, but runs into problems upon seeing that Caroline is a pompous know-it-all who won't work with her teammates.

With Glascott needing to have a bunion removed, he asks CB to assume the role of principal while he's out. Lainey tries to help CB when a problem arises with some mean girls, having experienced such groups before, but the power-hungry CB refuses to listen. Elsewhere, Julie is working toward earning her nurse practitioner certification, and Mellor becomes jealous when he learns her study partner, Leslie, is a man (James Lesure). Worse, Julie says she will be leaving the school to work in a hospital after getting her certification.

Mellor tells CB that his immature hobbies are turning off potential girlfriends, so CB tries to act more grown-up upon being smitten with Paloma (Chloe Bridges), a woman Glascott brought in to help William Penn be more eco-friendly. However, when Paloma wants to save an endangered bird population that lives right where Mellor plans to build the new baseball stadium, CB has to reach into his old bag of tricks. Meanwhile, Wilma tries to convince Lainey, head of the yearbook committee, to end the "senior superlatives" tradition because the awards are often hurtful. But Wilma reverses her stance upon learning that she's been voted "Coolest Teacher".

In the series finale, With Lainey having broken up with Barry over the long distance relationship not working, Wilma encourages her to confront her feelings for CB, but CB is now in a budding relationship with Paloma. When Paloma tells Lainey and Wilma she's considering a summer assignment in Brazil, Lainey encourages her to follow her dreams, even if it means leaving CB behind. Lainey later realizes she does have feelings for CB that go beyond friendship, only to learn he wants to travel with Paloma. At prom, Lainey asks CB not to go to Brazil, and when he asks why, she kisses him. Meanwhile, Toby is overjoyed when Dawn, a popular senior, asks him to prom. However, Mellor and Glascott later find out that Dawn only asked Toby because her parents will approve of him, and she intends to ditch him at prom for her real boyfriend, who's a known troublemaker. Mellor then tries to figure out how to tell Toby without hurting him too much.

Featured Song: "Dreams" by The Cranberries