Sanaa Lathan
Sidney 'Sid' Shaw
Taye Diggs
Andre Romulus 'Dre' Ellis
Yasiin Bey
Chris Anton 'Cav' Vichon
Nicole Ari Parker
Reese Marie Wiggam Ellis
Boris Kodjoe
Kelby Dawson
Queen Latifah
Francine
Wendell Pierce
Simon
Erik Weiner
Ren
Marc John Jefferies
Young Dre
Angie Martinez
Self (Radio DJ)
Rosalyn Coleman
Trish Hofmann
Venida Evans
Older Woman
Brette Taylor
Woman 2
Donna DuPlantier
Woman 3
Sterling K. Brown
Co-Worker
Big Daddy Kane
Self
Questlove
Self
Kool G Rap
Self
Helmar Augustus Cooper
Reverend
Toks Olagundoye
Sidney's LA Assistant
Opal Alladin
Crafts Vendor
Dana Dane
Self
Doug E. Fresh
Self
Jermaine Dupri
Self
Kimora Lee Simmons
Self
Russell Simmons
Self
Beanie Sigel
Self
Talib Kweli
Self
Common
Self
Method Man
Self
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)
Spencer Kayden
Bridesmaid (uncredited)
Joanie Laurer
Woman at Party (uncredited)
Reggi Wyns
Ten
Melissa Martínez
Meghan
Aaliyyah Hill
Young Sidney
Keith Tisdell
Richard Lawson
Breece Wilson
Woman
Robin T. Kirksey
Bartender 1
Kofi Boakye
Host
Dena Atlantic
Hot 97 Assistant
Gerry Pinzon
Instructor
Sam McPherson
Iridium Waiter
Tariq Trotter
Self - Black Thought [The Roots]
Wyking Jones
Bartender
Slick Rick
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]
Hadley Martin Fisher
Backstage Bartender
Justin 'DJ' Spaulding
Kid in the Park
Erica Ise
Bridesmaid (uncredited)
Brother Eden Douglas
Park Chess Player #1 (uncredited)
