The series opens with the arrival of Jamal Grant and Chris Anderson to Manny High School. Both make different entrances with Jamal paying guys to walk him to school as his posse and Chris driving his Dad's car. El Train warns Jamal that he's dead meat if he even thinks about painting over his graffiti. Chris learns about it and proceeds to paint over it. In the end they both get assigned to do a video year book for the school year.

Chris' mom learns Manhattan High does not have a Music Department because of lack of money, she vows to throw a fundraiser at the Anderson home. When she learns of Jamal's musical talents, she invites him to headline the event. Chris, however, is jealous of the attention his mom pays Jamal. He tries to discredit Jamal by revealing Jamal's checkered school career. Chris and his mom argue at the fundraiser and he storms out of the house.

Shakespeare in the Park is playing the same time as Chris's Knicks and Lakers game. Chris and Jamal are expected to tape the play, but they get Dawn to tape the play. Meanwhile Cassidy, Jamal and Chris got to the game and get caught when Ms. Noble sees them on the tv. Chris and Jamal let Cassidy take the blame until they decide to admit the truth.

Alberto is delivering drugs for a drug dealer and doesn't know it. So the boys devise a plan to blackmail the dealer into leaving Alberto alone.

The Spring Dance returns to Manny High. Chris tries to get Cassidy to go to the dance with him. She rejects him and Chris encounters Jamal's sister. He asks her to the dance without Jamal knowing about it. El Train wants to go to the dance with Cassidy and gets the nerve to ask her. Al wants to DJ at the party, but Dawn refuses until Al gets rid of the competition. Jamal doesn't like his sister going to the dance with Chris. He tells Kaisha that Chris is no good for her and she responds to telling him to let her make her own choices.

After getting into a fight with his father, Chris moves in with Jamal and his father. Chris soon realizes that not every father and son relationship is like his. Eventually Chris and his father settle their differences. Dawn and Cassidy ask Al if he has any ""connections"" on how to get tickets for an upcoming Jim Carrey movie.

Jamal convinces Chris to have a party and drive his father's car after Chris reveals that his parents forgot his birthday. However it is the complete opposite when they return home with a birthday celebration on thier mind.

Dawn and Cassidy both run for Student Council President with Jamal and Chris as their individual advisors. Dirty politics arise and even Alberto and El Train get tired of it and El Train decides to run at the last minute.

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Jamal reconsiders the value of spending time studying after his new friend, Charlie, a straight-A Manhattan High student, is killed by a drunk driver. But with the PSATs coming up in a few days, everyone tries to cope with the loss.

Chris uses Jamal's skills at guessing the results of games and gets them both into trouble.

Chris falls for an older woman. Afraid she'll dump him, Chris tells her that he's an under cover cop only to discover that she's his new student teacher.

Karen goes to the hospital as a patient. While she is staying there, Jamal remebers the time of his mother's death and how Karen reminds him so much about his mother.

One of Jamal's friends finally gets out of juvenile Hall and returns. He then proceeds to continue doing the things that led him to the hall in the first place. Meanwhile Chris is trying to finish the school project that he and Jamal were assigned to in the first episode.

Chris and Jamal end up in jail after getting caught with fake IDs. But the situation worsens when Al and El-Train (Steven Daniel) come to bail the guys out and end up behind bars as well. Meanwhile, Dawn and Cassidy offer their tutoring services at the school fundraising auction, but they're worried that Vinnie and Rocco have more than tutoring on their minds when they bid on the girls.

Chris and Jamal uncover the school's old radio station. The station is restarted and quickly ended after an unapproved song gets played on the air. The boys now have to figure out how to get the station back on the air.

El-Train has a fight with his mom and decides to move out of his home. But when Chris lets El-Train stay at his Park Avenue penthouse, he soon realizes that El-Train isn't interested in going back home anytime soon, so he has to come up with a plan to get El-Train back with his mother. Meanwhile, Al asks Cassidy and Dawn to be models for a photo shoot, but the girls become angered when they see where the photos end up.

After being robbed at gunpoint during the nighttime, Jamal buys a gun himself to feel safe.

Chris finds out that his parents are getting a divorce, he becomes a recluse and blames himself for their breakup. But his friends help him realize that it was not his fault and that he should talk things out with his parents.

After El-Train beats up a local bully, he starts reverting back to his own days of bullying people, and even begins to isolate his friends. But when Miss Noble gets ahold of him, she reminds him of how far he's come, forcing him to think twice about his attitude, and his next schoolyard fight. Meanwhile, Dawn is embarrassed after a terrible date with school quarterback Brent (guest star Scott Hamm), where she tried to pass herself off as a football expert and ended up looking like a fool.

Jamal asks Cassidy if she can get her new boyfriend, 98 singer Nick Lachey, to perform with the rest of the group at an 'unofficial' school dance on the roof of Manhattan High. Although the dance is supposed to be kept a secret from Miss Noble, the gang soon realizes the consequences of trying to fool the principal.

Chris decides to go on a date with one of the callers to his radio show, but when he sees that she dresses like a Goth, he is unsure about whether or not to go out with her again, even though he likes her. Meanwhile, El-Train leads the gang in throwing a surprise party for Miss Noble's tenth anniversary at Manny High.

Miss Noble asks Jamal and Chris to become big brothers as part of a class project. But their little brother, Ernesto, turns out to be a handful of trouble, especially when he keeps disappearing on the guys. Meanwhile, Cassidy tries to pass Driver's Education again, but first she has to get by the very strict teacher's assistant, El-Train.

Cassidy starts taking pills when she is overworked.

Ms. Noble quits after the students take her for grant one too many time. She returns when her replacement gets out of control.