Randy Wagstaff, played by Maestro Harrell, is an enterprising eighth-grade student who is dependent on social services. He is a pupil at Edward Tilghman Middle School and is friends with Namond Brice, Michael Lee and Duquan "Dukie" Weems. He lives with a foster mother, Miss Anna, who seems to instill some discipline in his life. He is well known amongst his peers for his imagination and ideas. Randy runs a small business selling snacks and soft drinks to his peers and neighborhood drug dealers.