Guest Stars Zabryna Guevara as Mrs. Cruz Jaden Smith as Marcus Kipling Stefanée Martin as Yolanda Kipling Shyrley Rodriguez as Regina Daveed Diggs as Adult Books Giancarlo Esposito as Pastor Ramon Cruz Kevin Corrigan as Jackie Moreno Judy Marte as Wanda Lillias White as Fat Annie Brandon J. Dirden as Leon Mamoudou Athie as Grandmaster Flash Eric Bogosian as Roy Asheton Michel Gill as Mr. Gunns Karen Aldridge as Adele Kipling Frank Wood as Ed Koch Ron Cephas Jones as Winston Kipling Jeremie Harris as Shane Vincent Eric D. Hill Jr. as DJ Kool Herc Okieriete Onaodowan as Afrika Bambaataa Co Starring Jason Genao as Napoleon King Feliciano as Lopez Willie Estrada as Willie Omar Sharif Scroggins as E Barrington Walters, Jr. as Doo-Wop Jarrett Brown as Halfback Joseph Cardoso as Shorty Danai Kadzere as Carmelita Keenan Jolliff as Marshall Strawbridge Rony Clanton as Elderly Black Waiter Nick Bailey as Fish Joe Curnutte as Chips Steven Hauck as Dr. Campbell Grant Roe Hartrampf as Tate Poindexter
