Guest Stars Zabryna Guevara as Mrs. Cruz Jaden Smith as Marcus Kipling Shyrley Rodriguez as Regina Stefanée Martin as Yolanda Kipling 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 Michel Gill as Mr. Gunns Karen Aldridge as Adele Kipling Frank Wood as Ed Koch Tory Devon Smith as Little Wolf Ron Cephas Jones as Winston Kipling Yolonda Ross as Ms. Green Evan Parke as Wolf Sal Rendino as Stanley Kelly Billy Porter as DJ Malibu Co Starring Jason Genao as Napoleon Tremayne Rollins as Daze Mikey D'Astoli as Crash King Feliciano as Lopez Jordan Mahome as Slim Willie Estrada as Willie Salma Isabel Salinas as Angela Jaden Michael as Rafe Keenan A. Jones as Byron Sebastian Chacon as Stevie Boy Irma-Estel LaGuerre as Evelyn Ceazar Reyes as Bully #2 Brian Newby as Get Down Bully #2 Isaiah Negrón as Baron Gerald Jones III as Baby Thug Dalon J. Holland as Heckler Corey Royster as Corey the Coke Dealer Tevin Thompson as Bully #1 Steven Solis as Luis Bryant Dope as Cowboy Ivan Cofield as Get Down Bully #1 West Barrington Artope as Sunset Jordan Anderson as Bully #3 José Alvarez as Jose Luciano Acuna Jr. as Senior Savage Warlord #1 Malcolm C. Murray as Barman John Adams as Fuerte's Host Omar Soriano as Doorman Louis Arcella as El Tio Mario D'Leon as Bouncer #2 Conrad Roberts as Uncle Johnny Jeff Lima as El Viejo