- Melissa Martínez - Meghan
- Aaliyyah Hill - Young Sidney
- Marc John Jefferies - Young Dre
- Angie Martinez - Self (Radio DJ)
- Rosalyn Coleman - Trish Hofmann
- Keith Tisdell - Richard Lawson
- Venida Evans - Older Woman
- Breece Wilson - Woman
- Brette Taylor - Woman 2
- Donna DuPlantier - Woman 3
- Robin T. Kirksey - Bartender 1
- Sterling K. Brown - Co-Worker
- Kofi Boakye - Host
- Dena Atlantic - Hot 97 Assistant
- Gerry Pinzon - Instructor
- Sam McPherson - Iridium Waiter
- Big Daddy Kane - Self
- Tariq Trotter - Self - Black Thought [The Roots]
- Questlove - Self
- Kool G Rap - Self
- Helmar Augustus Cooper - Reverend
- Wyking Jones - Bartender
- Toks Olagundoye - Sidney's LA Assistant
- Opal Alladin - Crafts Vendor
- Dana Dane - Self
- Doug E. Fresh - Self
- Slick Rick - Self
- Jermaine Dupri - Self
- Pete Rock - Self
- David Jolicoeur - Self - Trugoy the Dove [De La Soul]
- Kelvin Mercer - Self - Posdnuos [De La Soul]
- Vincent Mason - Self - Maseo [De La Soul]
- Kimora Lee Simmons - Self
- Russell Simmons - Self
- Beanie Sigel - Self
- Talib Kweli - Self
- Common - Self
- Method Man - Self
- Hadley Martin Fisher - Backstage Bartender
- Justin 'DJ' Spaulding - Kid in the Park
- Liza Lapira - Hot 97 Receptionist
- Ralph E. Tresvant - Royale (uncredited)
- Kevin Watson - Record Label Executive (uncredited)
- Vinny DeGennaro - Bouncer (uncredited)
- Lamman Rucker - Man on Couch at Radio Station (uncredited)
- Erica Ise - Bridesmaid (uncredited)
- Spencer Kayden - Bridesmaid (uncredited)
- Chyna - Woman at Party (uncredited)
- Brother Eden Douglas - Park Chess Player #1 (uncredited)
Capítulo disponible en las siguientes plataformas:
