Full of the humour, mild humiliation, and bittersweet lessons of growing up, this coming-of-age comedy from Malcolm D. Lee unfolds on the South Side of 1970's Chicago.

Xavier (Bow Wow) and his wisecracking crew of friends rule the local roller skating rink, but when it closes their summer looks to be an empty one. Reluctantly, they head over to Sweetwater, the glitzy rink across town where the rich kids skate, and where the cocky Sweetness (Wesley Jonathan) presides over all as the unchallenged king of the floor. The boys are ridiculed upon their arrival, and soon vow revenge at the upcoming competition, for which they begin to hone their skills. Meanwhile, X deals with his troubles at home, as his mother has recently died and his dad, Curtis (Chi McBride), struggles to make ends meet. The two attempt to understand each others' grief, and help one another to move beyond it. X also makes the acquaintance of new kid Tori (Jurnee Smollett), a gawky girl with braces and a sharp tongue, who tags along with the boys as an ugly duckling, later to emerge a swan. Tori's, rather attractive, mum (Kellita Smith) attracts a great deal of attention on the block, notably from two quick-talking garbage men (Mike Epps and Charles Q. Murphy in a hilarious bit part), and X tries to navigate his budding relationship with the seemingly-unattainable Naomi (Meagan Good).