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

Tariq Trotter

Self - Black Thought [The Roots]

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

Slick Rick

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)

Chyna

Woman at Party (uncredited)