City Guys - Season 5 (2001)

Chris meets Cassidy's father for the first time. Dawn vows with the help of Al to rid Ms. Noble of her addictive smoking habit.

Dawn has trouble accepting that Al has started dating a new girl so soon after their break up. Meanwhile, Chris, Jamal and El-Train hold a survivor type competition in the park with Ms. Noble overseeing.

Jamal teams up with Malcolm, his dance nemesis to audition as backup dancers for a group called six-street. Dawn and Cassidy ask Al and El-Train to secretly take over their advice column for women temporarily so they can attend a taping of Late Night with Conan O'Brien (1993). The column becomes a bigger success, but it proves to be an unfavorable double-edged sword for the two when Al and El-Train decide to manipulate the column for their own purposes.

The gang gets involved with a music group trying to make it big.

It is senior ditch day at Manny High. Jamal and Chris want to spend this special day bungee jumping with Cassidy, Al, and El-Train. Ms. Noble tells them they can't go because they have to have a radio-thon to raise money for children. Jamal and Chris decide to skip this and rig their radio booth with pre-taped reel-to-reels of their show. Meanwhile, Dawn fights against a student named Kitty Collins for the attention of Ms. Noble and the title of valedictorian.

Dawn falls for and starts dating Chris's old friend, Jack from his former prep school and she tells Cassidy that he might be the one. Chris finds out that Jack is still with his old girlfriend and Cassidy tries to tell Dawn, but she doesn't believe her. Dawn confronts Jack who tells her that it is over between him and his old girlfriend, but later finds out that she had been lied to. El-Train hits the road with Al and Jamal in his fixed up van to go attend a DMX concert. On the way, they pick up a hitchhiker who robs them and leaves the three tied up on the side of ...

Jamal falls for and after some mistakes in introducing himself, he hooks up with and starts dating one of the waitresses at the Manhattan diner named Rosie. She is very independent and not afraid to speak her mind, which proves to be trouble when she begins to offend customers who get on her nerves at the diner. After numerous complaints, Mr. Grant gives his son the uncomfortable job of firing her.

Cassidy auditions for a play with a prominent Broadway director. She manages to get a small role but is thrilled just being in the play. Later, Chris sees the lead actress quit because the director is hitting on her. The director then gives Cassidy the lead role. Cassidy is thrilled until Chris tells her what happened to the other actress. Instead of believing him, she thinks he's just jealous that she's spending so much time with the director. But when the director comes on to Cassidy, she realizes Chris was right. The gang then sets up as sting operation on the ...

There is a heat wave going through New York. Dawn convinces Ms. Noble to allow a small waiting pool on the roof of Manny High. Instead Al and Chris secretly set up a large swimming pool for the whole school to enjoy and relax. Ms. Noble later finds out about the pool when one of the many interruptions preventing her from having a peaceful lunch break is leaking water coming from the ceiling. She tells Al to get rid of the pool. Before he does this, Al attempts to conquer his fear of the pool and learn how to swim, but in the process he almost drowns. Ms. Noble comes ...

Jamal wants to get into USC but his coach tells him that he isn't in shape enough to be considered for the team. He starts working out and is offered steroids at the health club. Meanwhile, Dawn, Cassidy, Chris and Al have to deal with a cruel pottery teacher. Ms. Hotz scares the students and they eventually fight back. She reveals that she is only mean because most people take her class due to her sexy looks.

El-Train believes that by participating in any form of sports competition against his new girlfriend, Kianna will result in conflict which will lead to the disintegration of their relationship. He comes to the conclusion of this by witnessing Kianna become riled up during Chris and Jamal's radio show over wanting to beat El-Train in the basketball shoot out competition at the recreation center. Meanwhile Jamal, Chris, and Cassidy work extremely hard to appease a newspaper food critic who has given a bad review to the Manhattan Diner. Also, Dawn develops a crush on ...

Overwhelmed by all the test prep, El-Train decides not to take the SATs.

Dawn is running for Senior Class President against a pompous and overconfident student named Thane Watkins. Jamal and Chris contribute to Dawn losing out on the position when they make a mockery of the whole election on their radio show which affects the voter turnout. In turn making Thane win by a landslide and unwittingly giving him the power to mess with many Manny High programs and to act on his distaste of their radio show by canceling it and dismantling the radio booth. Now Chris, Jamal, Al, and El-Train must work with Dawn to veto this decision. Meanwhile, ...

El-Train becomes popular among the ladies during the reciting and singing of his poetry which causes him to pay less attention to his girlfriend, Kianna. Meanwhile, Al, Chris and Jamal attempt be the first students to prank Ms. Noble during her tenure as the Principal of Manny High.

The gang is having problems over a yearbook picture and are giving each other the silent treatment. So Ms. Noble calls everybody to Manny High on Saturday to work things out by reflecting on memories of the good, the bad, and the ugly that they had over the span of their time as friends.

A model agency is recruiting girls for their magazine. Jamal's girlfriend, Rosie, signs up and gets featured in the magazine. Jamal is having problems with guys oogling his girlfriend.

After Chris, Jamal and El-Train survive a car crash, they start going through some changes as they now view life in a whole new perspective. The three friends begin live to their lives on the edge by doing certain activities to the extreme.

The time for Ms. Noble's retirement and the gang's graduation is drawing near and everybody is excited, except for Dawn. Witnessing the preparation for next year and the new changes being made at the school makes Dawn uneasy. She begins to become anxious about moving on from Manny High and the thought of being apart from her friends when they all go their separate ways in the fall.

The students of Manny High have a statue made of Ms. Noble in honor of her tenure as principal of Manny High placed near the front of the school. At the tribute, Ms. Noble tells the gang that there is an opening to produce a television show for Manny High. Chris and Jamal turn it down because they are already busy working on their radio show. Dawn, Cassidy, El-Train, and Al take on the job by creating and producing a spoof of Buffy contre les vampires (1997) entitled "Muffy the Werewolf Slapper". Jamal and Chris find out that their radio show will be competing with the TV show during lunch time and ...

The gang all prepare for the Manny High Prom. Chris prepares to give a ring to Cassidy for this special occasion and to highlight their relationship. He also wants her to visit him at Duke University from Cal Art. Cassidy and Dawn misinterpret his message about the ring as a marriage proposal and the Duke brochures as Chris wanting Cassidy to go with him to Duke. Meanwhile, Al asks Dawn to the prom and she accepts. At the prom, the two fondly reflect on the memories of their time together when they were dating. Ms. Noble worries that by Billy being away, this will be ...

The whole gang is getting ready for graduation, but they are sent the wrong diplomas. There is another problem when El-Train might not be able to graduate. Things all work out in the end when they receive their correct diplomas and El-Train receives the credit he needs to graduate by performing in a play. Chris and Jamal have to find a way to end their radio show. A bizarre twist of fate hooks them up with the perfect goodbye. They attend graduation.

A few months have passed since Ms. Noble has retired as Principal and Jamal, Chris, Cassidy, El-Train, Dawn, and Al have graduated from Manny High. Ms. Noble and the gang decide to have a final farewell meal at the Manhattan diner before they head off to the beginning of a new chapter in each of their lives. They fondly look back at the memories of the good times, as each member of the gang departs and says their goodbyes.

At his new job, Al attempts to advertise a toy gun without violence and gore, which is against his boss's wishes. Meanwhile, Ms. Noble has signed up Chris, Jamal, El-Train, Dawn and Cassidy to the Manny High marching band against their will to fulfill their Arts elective credit for graduation.