ATL
Rashad (T.I.) is a teen living in Atlanta, Georgia with his Uncle, George (Mykelti Williamson) and his little brother Ant (Evan Ross). He and his brother were raised by their uncle George since their parents died in a car accident, and they work with him as part of his custodial company. 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 does not see much of a future in that field as he has 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 will 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, known as "The Ones", on Sunday nights at Cascade, a 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 is 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 his Chevrolet El Camino. However, 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 starts dating a girl named Tondie (April Clark), who takes a liking to him only after he began to make money through drug dealing.
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, whose real name is Erin. Erin says that she will 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 that 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 that he will 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. Rashad tracks the two down and throws the money that Ant owes Marcus in his face. Marcus then holds Rashad at gunpoint and makes a rude comment. Rashad knocks the gun off of Marcus's hand, it goes off, and they fight briefly until Rashad gets up to leave. Rashad tells Ant to get into the car while Marcus grabs his gun and ends up shooting Ant (later revealed) in the chest. At the hospital, Rashad and Ant are able to reconnect; likewise, Erin, Esquire, and Rashad make peace, as the scene ends with the poem "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,as Big Gipp makes a cameo appearance in his shop, 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. Uncle George starts attending church more often and finds a good woman to date. 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. The film ends with Rashad leaving his skates in Cascades, and the building's lights go off.
flashback