- Erika Alexander - Linda Diggs
- Uyoata Udi - Rebel / Inspectah Deck
- Uyoata Udi - Inspectah Deck
- Damani D. Sease - U-God
- Cody Johns - Ethan
- David J. Cork - Kenny Smith
- Motell Gyn Foster - Just-Ice
- J. Bernard Calloway - Rodney
- Corey Hibbert - Crack Fiend
- JQ Cole - B-Black
- Joey Bada$$ - Rebel
- Mark Sussman - Ferry Speaker
- Jamad Mays - Big Daddy Kane
- Max Woertendyke - Magazine Reporter
- Patrick Ssenjovu - African Vendor
- La La Anthony - Tracey Waples
- Justus Davis Graham - Randy Diggs
- Ebony Obsidian - Nia
- Amyrh Harris - Darren Coles
- Trayce Malachi - Young Bobby
- Jake Hoffman - Steve Rifkind
- JaQwan J. Kelly - Jamel
- Bokeem Woodbine - Jerome
- Gbenga Akinnagbe - Mook
- Jorge Lendeborg Jr. - Jah Son
- Stephen McKinley Henderson - Uncle Hollis
- Jason Louder - Cressy
- Curtiss Cook Jr. - Mathematics
- Travis Raeburn - Dada
- Adriane Lenox - Shotgun's Grandma
- Jamie Hector - Andre D'Andre
- Tangela Wilson - Ms. Ward
- Vincent Pastore - Fat Larry
- Andrea-Rachel Parker - Mama Ganja
- Andrea-Rachel Parker - Momma Ganja
- Delissa Reynolds - Ann Coles
- Malcolm Xavier - Haze
- Nuri Hazzard - Byron
- Paola Lázaro - Tonya
- Robert Crayton - Attila
- Reginald L. Barnes - Raf
- Jimi Stanton - Pat
- Ron Yuan - Lord
- Andy Le - Fang
- Brian Le - Zang Wei
- Dante Hoagland - Kid #1
- Jill Flint - Monica Lynch
- Jason E. Kelley - Uncle Anthony
- Imani Lewis - Roxanne Shante
- Imani Lewis - Roxanne Shanté
- Chauncey Johnson - Eric B
- Chauncey Johnson - Eric B.
- Dee Rogers - Young Haze
- Marcus Gladney Jr. - Isaiah
- Tonya Pinkins - Burgess
- Sullivan Jones - Officer Steven Marcus
- Diane Howard - Laurie
- Daniel Augustin - Rakim
- Ezra Knight - Reverend Williams
- Caleb Castille - Darryl 'Chino' Hill
- Caleb Castille - Chino
- Kecia Lewis - Aunt Goldie
- Emily Kimball - Carly
- Jermel Wilson - Scarface
- Christian Combs - Sean "Puff Daddy" Combs
- Wavyy Jonez - Christopher "Biggie Smalls" Wallace / The Notorious B.I.G.
- Kelsey Caesar - Nasir "Nas" Jones
- Louie Gomez - Fat Joe
- James Adam Tucker - Wilbert Hart
- Nate Bynum - William Hart
- Jaison Hunter - Prince Paul
- Freddy Zambrana - RNB Singer (uncredited)
- Freddy Zambrana - Pedestrian (uncredited)
- Wally Ng - Chinese Dude
- Eif Rivera
- Matthew Ross
- Jet Wilkinson
- Janice Cooke
- Mario Van Peebles
- Malcolm D. Lee
- Earl Davis
- Alex Tse
- Solange Morales
- Chelsey Lora
- Michael C. Martin
- Ryan O'Nan
- Rodney Barnes
Ashton Sanders interpreta a Bobby Diggs en la serie.
Siddiq Saunderson hace el papel de Dennis 'D-Love' Coles.
Shameik Moore interpreta a Sha Raider en la serie.
Julian Elijah Martinez interpreta a Mitchell 'Divine' Diggs en la serie.
Zolee Griggs interpreta a Shurrie Diggs en la serie.
T.J. Atoms interpreta a Ason Unique en la serie.
Marcus Callender interpreta a Oliver 'Power' Grant en la serie.
Dave East interpreta a Shotgun en la serie.
Johnell Young hace el papel de Gary.
Uyoata Udi interpreta a Inspectah Deck en la serie.
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