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 Evan Parke as Wolf Yolonda Ross as Ms. Green Sal Rendino as Stanley Kelly Billy Porter as DJ Malibu Co Starring Jason Genao as Napoleon Mikey D'Astoli as Crash King Feliciano as Lopez Tremayne Rollins as Daze Jordan Mahome as Slim Willie Estrada as Willie Salma Isabel Salinas as Angela Jaden Michael as Rafe Keenan A. Jones as Byron Conrad Roberts as Uncle Johnny Luciano Acuna Jr. as Senior Savage Warlord #1 Ceazar Reyes as Bully #2 Isaiah Negrón as Baron Tevin Thompson as Bully #1 Dalon J. Holland as Heckler Gerald Jones III as Baby Thug Irma-Estel LaGuerre as Evelyn Steven Solis as Luis Brian Newby as Get Down Bully #2 Corey Royster as Corey the Coke Dealer 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 Malcolm C. Murray as Barman Sebastian Chacon as Stevie Boy John Adams as Fuerte's Host Omar Soriano as Doorman Louis Arcella as El Tio Mario D'Leon as Bouncer #2 Jeff Lima as El Viejo