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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) Joan Marie Laurer Woman at Party (uncredited)