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

Reggi Wyns

Ten

Melissa Martínez

Meghan

Aaliyyah Hill

Young Sidney

Marc John Jefferies

Young Dre

Angie Martinez

Self (Radio DJ)

Rosalyn Coleman

Trish Hofmann

Keith Tisdell

Richard Lawson

Venida Evans

Older Woman

Breece Wilson

Woman

Brette Taylor

Woman 2

Donna DuPlantier

Woman 3

Robin T. Kirksey

Bartender 1

Sterling K. Brown

Co-Worker

Kofi Boakye

Host

Dena Atlantic

Hot 97 Assistant

Gerry Pinzon

Instructor

Sam McPherson

Iridium Waiter

Big Daddy Kane

Self

Tariq Trotter

Self - Black Thought [The Roots]

Questlove

Self

Kool G Rap

Self

Helmar Augustus Cooper

Reverend

Wyking Jones

Bartender

Toks Olagundoye

Sidney's LA Assistant

Opal Alladin

Crafts Vendor

Dana Dane

Self

Doug E. Fresh

Self

Slick Rick

Self

Jermaine Dupri

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]

Kimora Lee Simmons

Self

Russell Simmons

Self

Beanie Sigel

Self

Talib Kweli

Self

Common

Self

Method Man

Self

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)