Sanaa Lathan as Sidney 'Sid' Shaw

Taye Diggs as Andre Romulus 'Dre' Ellis

Yasiin Bey as Chris Anton 'Cav' Vichon

Nicole Ari Parker as Reese Marie Wiggam Ellis

Boris Kodjoe as Kelby Dawson

Queen Latifah as Francine

Wendell Pierce as Simon

Erik Weiner as Ren

Reggi Wyns as Ten

Melissa Martínez as Meghan

Aaliyyah Hill as Young Sidney

Marc John Jefferies as Young Dre

Angie Martinez as Self (Radio DJ)

Rosalyn Coleman as Trish Hofmann

Keith Tisdell as Richard Lawson

Venida Evans as Older Woman

Breece Wilson as Woman

Brette Taylor as Woman 2

Donna DuPlantier as Woman 3

Robin T. Kirksey as Bartender 1

Sterling K. Brown as Co-Worker

Kofi Boakye as Host

Dena Atlantic as Hot 97 Assistant

Gerry Pinzon as Instructor

Sam McPherson as Iridium Waiter

Big Daddy Kane as Self

Tariq Trotter as Self - Black Thought [The Roots]

Questlove as Self

Kool G Rap as Self

Helmar Augustus Cooper as Reverend

Wyking Jones as Bartender

Toks Olagundoye as Sidney's LA Assistant

Opal Alladin as Crafts Vendor

Dana Dane as Self

Doug E. Fresh as Self

Slick Rick as Self

Jermaine Dupri as Self

Pete Rock as Self

David Jolicoeur as Self - Trugoy the Dove [De La Soul]

Kelvin Mercer as Self - Posdnuos [De La Soul]

Vincent Mason as Self - Maseo [De La Soul]

Kimora Lee Simmons as Self

Russell Simmons as Self

Beanie Sigel as Self

Talib Kweli as Self

Common as Self

Method Man as Self

Hadley Martin Fisher as Backstage Bartender

Justin 'DJ' Spaulding as Kid in the Park

Liza Lapira as Hot 97 Receptionist

Ralph E. Tresvant as Royale (uncredited)

Kevin Watson as Record Label Executive (uncredited)

Vinny DeGennaro as Bouncer (uncredited)

Lamman Rucker as Man on Couch at Radio Station (uncredited)

Erica Ise as Bridesmaid (uncredited)

Spencer Kayden as Bridesmaid (uncredited)

Chyna as Woman at Party (uncredited)