ATL
Rashad (Harris) is a teen living in Atlanta with his Uncle George (Williamson) and his little brother Ant (Ross). He and his brother have been raised by George since their parents died in a car accident, and they work with him at the Swann Cleaning Service, the family's business which George took over when Rashad's parents passed. When not working or finishing his last year of high school, Rashad spends most of his time with his friends Brooklyn (Albert Daniels), Teddy (Jason Weaver), and Esquire (Jackie Long). Rashad is a talented artist but doesn't see much of a future in that field as he's become accustomed to working the family business. Esquire, Rashad's best friend, goes to a prep school on the opposite side of town from where they live, and is trying to attend an Ivy League college after senior year. However, he finds out that he'll need a letter of recommendation from someone of high stature to better his chances of acceptance at the school he wants to attend.
Rashad and his friends are also a skate crew on Sunday nights at Cascade, a local skating rink where local teens hang out. While there, Rashad catches the eye of New New (Lauren London), a round-the-way girl with a mysterious background, since he only sees her around when she's hanging out with her friends Veda (Khadijah Haqq) and Star (Malika Haqq). The two become attracted to one another and they later kiss when he gives her a ride home; in contrast, Esquire instantly develops a disliking for Rashad's new love interest, considering her bad company. Meanwhile, no longer under Rashad's watchful eyes, Ant becomes involved with a drug dealer named Marcus (Patton) and begins to sell for him. He also wins his dreamgirl, his classmate Tondie (April Clark) and they make love in the back of a car.
At work one day, Esquire meets John Garnett (Keith David), a millionaire who heads a successful business venture called the United Express. The two quickly become friends, with Garnett's admiration for Esquire's ambition and Esquire's respect for Garnett's success driving the relationship. Esquire sees an opportunity to obtain the letter of recommendation that would bring about his acceptance to his primary college choice. When Esquire goes to Garnett's house to pick up the letter, he meets his daughter Erin, who, to his surprise, turns out to be New New. Erin says she'll reveal where Esquire is really from (something he lied to her father about) if he tells Rashad about her.
Things soon begin to fall apart for Rashad; Ant is arrested for selling weed, and later Rashad finds out the truth about Erin. He no longer speaks to his friends, realizing Esquire knew about Erin the whole time. Esquire, feeling guilty about the way he obtained the letter, decides to return it to Garnett, and reveals the truth about himself and his background. He, Brooklyn, and Teddy attempt to make peace with Rashad and ask him to attend Skate Wars, Cascade's annual skate competition, with them; Rashad, however, refuses their offer. Just as he decides he'll go after being persuaded by his uncle, he finds out that Marcus is looking for Ant on the streets, searching for cash that Ant owes to him. Although Rashad is able to track the two down, Ant is shot by Marcus, albeit not fatally. At the hospital, Rashad and Ant are able to reconnect; likewise, Erin, Esquire, and Rashad make peace, as the scene ends with the poem "A Love's Deceit" by rapper Big Rube playing.
In the film's final scene, Teddy opens his own business concerning the production of gold teeth, Brooklyn finds a job at a Krystal restaurant, while Esquire receives a mysterious letter of recommendation (presumably from Garnett) and is able to attend his college. The twins Veda and Star remain in the old neighborhood and hang out at Cascade on Sundays, while Erin goes to Spelman College, the school she wanted to attend. Ant changes direction, discarding the notion of drug dealing, finds a new girlfriend and begins to focus on his studies in school. Rashad, lastly, becomes a comic artist for the Sunday edition of the Atlanta Evening Standard, the city's newspaper.
