Jamal Wallace (ROB BROWN) is a smart, sixteen-year-old who lives in the Bronx with his mom, Janice (STEPHANIE BERRY), and older brother, Terrell (BUSTA RHYMES). An avid reader and writer, Jamal is a classic underachiever who'd rather play basketball with his buddies, including Fly (FLY WILLIAMS III), then let them know how smart he is by doing well in school.
Although his class grades are just average, his exemplary test scores as well as his prowess on the basketball court draw the attention of officials from Mailor-Callow, an exclusive Manhattan prep school, who want to give Jamal a full scholarship to attend.
In the meantime, Jamal takes a dare from his friends to climb up into the apartment of a mysterious man they always see watching them playing basketball from his window. Scared away once inside, Jamal forgets his backpack full of his writings in the apartment, but later has it thrown down to him by the still anonymous man.
Checking to make sure everything is there, Jamal discovers that the man has made critical notes about his writing. Intrigued by this, Jamal returns to the apartment and enters into an unlikely and unusual friendship with William Forrester (SEAN CONNERY), a famous writer known for his highly acclaimed but sole work, "Avalon Landing," that was published in the 1950s. Now a recluse, Forrester is intrigued by this young man who's so full of potential.
As Jamal enrolls at Mailor-Callow where he makes friends with Claire Spence (ANNA PAQUIN) and takes a writing class taught by a haughty professor, Robert Crawford (F. MURRAY ABRAHAM), he and Forrester end up teaching each other a thing or two about writing and life.