The series was very similar in style to Saved by the Bell, but with an urban setting and more diverse cast.
City Guys was mainly centered on its two main characters, Jamal Grant (Wesley Jonathan) and Chris Anderson (Scott Whyte), two teenagers from different backgrounds – Chris coming from a wealthy family, and Jamal coming from a working-class family – who had to stay on the ball while attending Manhattan High School (which was nicknamed in the series as "Manny High") and avoid trouble, while their principal Karen Noble (Marcella Lowery) attempted to keep them in line and out of trouble.
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.
However it is the complete opposite when they return home with a birthday celebration on their mind.
Dawn and Cassidy both run for Student Council President with Jamal and Chris as their individual advisors.
Jamal and Chris's similar personalities caused friction between them in the beginning, but they became best friends as the series went on.
The boys and their friends – overachiever Dawn Tartikoff (Caitlin Mowrey), slick guy Al Ramos (Dion Basco), aspiring actress Cassidy Giuliani (Marissa Dyan) and dimwitted bully-turned-friend (who was held back six grades) Lionel "L-Train" Johnson (Steven Daniel) – dealt with the typical teen issues, such as cheating on tests, peer pressure, racism, and dealing with school violence.
The series opens with the arrival of Jamal Grant and Chris Anderson at 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.
Shakespeare in the Park is playing the same time as Chris's Knicks and Lakers game.