Sanaa Lathan
Sidney 'Sid' Shaw
Taye Diggs
Andre Romulus 'Dre' Ellis
Yasiin Bey
Chris Anton 'Cav' Vichon
Nicole Ari Parker
Reese Marie Wiggam Ellis
Aaliyyah Hill
Young Sidney
Marc John Jefferies
Young Dre
Angie Martinez
Self (Radio DJ)
Rosalyn Coleman
Trish Hofmann
Keith Tisdell
Richard Lawson
Robin T. Kirksey
Bartender 1
Sterling K. Brown
Co-Worker
Dena Atlantic
Hot 97 Assistant
Sam McPherson
Iridium Waiter
Tariq Trotter
Self - Black Thought [The Roots]
Helmar Augustus Cooper
Reverend
Toks Olagundoye
Sidney's LA Assistant
Opal Alladin
Crafts Vendor
David Jolicoeur
Self - Trugoy the Dove [De La Soul]
Kelvin Mercer
Self - Posdnuos [De La Soul]
Vincent Mason
Self - Maseo [De La Soul]
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)
Joanie Laurer
Woman at Party (uncredited)
Brother Eden Douglas
Park Chess Player #1 (uncredited)
