Sidney 'Sid' Shaw

Sanaa Lathan

Dre

Taye Diggs

Chris

Mos Def

Reese

Nicole Ari Parker

Kelby

Boris Kodjoe

Francine

Queen Latifah

Ren

Erik Weiner

Simon

Wendell Pierce

Himself

Common

Ten

Reggi Wyns

Meghan

Melissa Martínez

Young Sidney

Aaliyyah Hill

Himself

Doug E. Fresh

Young Dre

Marc John Jefferies

Self (Radio DJ)

Angie Martinez

Trish Hofmann

Rosalyn Coleman

Richard Lawson

Keith Tisdell

Older Woman

Venida Evans

Woman 2

Breece Wilson

Woman 2

Brette Taylor

Woman 3

Donna DuPlantier

Bartender 1

Robin T. Kirksey

Co-Worker

Sterling K. Brown

Host

Kofi Boakye

Hot 97 Assistant

Dena Atlantic

Instructor

Gerry Pinzon

Iridium Waiter

Sam McPherson

Himself

Big Daddy Kane

Self - Black Thought [The Roots]

Tariq Trotter

Himself

Ahmir "Questlove" Thompson

Himself

Kool G Rap

Reverend

Helmar Augustus Cooper

Bartender

Wyking Jones

Sidney's L.A. Assistant

Toks Olagundoye

Crafts Vendor

Opal Alladin

Himself

Dana Dane

Himself

Slick Rick

Himself

Jermaine Dupri

Himself

Pete Rock

Self - Trugoy the Dove [De La Soul]

David Jolicoeur

Himself

Trugoy 'The Dove'

Self - Posdnuos [De La Soul]

Kelvin Mercer

Himself

Plugwon Posdnuos

Self - Maseo [De La Soul]

Vincent Mason

Self - Posdnuos [De La Soul]

Posdnuos

Himself

Vincent L. Mason

Herself

Kimora Lee Simmons

Himself

Russell Simmons

Himself

Beanie Sigel

Himself

Talib Kweli

Backstage Bartender

Hadley Martin Fisher

Self

Method Man

Kid in the Park

D.J. Jus

Hot 97 Receptionist

Liza Lapira

Kid in the Park

Justin 'DJ' Spaulding

Royale (uncredited)

Ralph E. Tresvant

Record Label Executive (uncredited)

Kevin Watson

Bouncer (uncredited)

Vinny DeGennaro

Man on Couch at Radio Station (uncredited)

Lamman Rucker

Bridesmaid (uncredited)

Spencer Kayden

Woman at Party (uncredited)

Joan Marie Laurer