Casting de Brown Sugar
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Sanaa LathanSidney 'Sid' Shaw
Taye DiggsAndre Romulus 'Dre' Ellis
Yasiin BeyChris Anton 'Cav' Vichon
Nicole Ari ParkerReese Marie Wiggam Ellis
Boris KodjoeKelby Dawson
Queen LatifahFrancine
Wendell PierceSimon
Erik WeinerRen- Reggi WynsTen
- Melissa MartínezMeghan
- Aaliyyah HillYoung Sidney
Marc John JefferiesYoung Dre
Angie MartinezSelf (Radio DJ)
Rosalyn ColemanTrish Hofmann- Keith TisdellRichard Lawson
Venida EvansOlder Woman- Breece WilsonWoman
Brette TaylorWoman 2
Donna DuPlantierWoman 3- Robin T. KirkseyBartender 1
Sterling K. BrownCo-Worker- Kofi BoakyeHost
- Dena AtlanticHot 97 Assistant
- Gerry PinzonInstructor
- Sam McPhersonIridium Waiter
Big Daddy KaneSelf
Tariq TrotterSelf - Black Thought [The Roots]
QuestloveSelf
Kool G RapSelf
Helmar Augustus CooperReverend- Wyking JonesBartender
Toks OlagundoyeSidney's LA Assistant
Opal AlladinCrafts Vendor
Dana DaneSelf
Doug E. FreshSelf
Slick RickSelf
Jermaine DupriSelf- Pete RockSelf
- David JolicoeurSelf - Trugoy the Dove [De La Soul]
- Kelvin MercerSelf - Posdnuos [De La Soul]
- Vincent MasonSelf - Maseo [De La Soul]
Russell SimmonsSelf
Beanie SigelSelf
Talib KweliSelf
CommonSelf
Method ManSelf- Hadley Martin FisherBackstage Bartender
- Justin 'DJ' SpauldingKid in the Park
Liza LapiraHot 97 Receptionist
Ralph E. TresvantRoyale (uncredited)
Kevin WatsonRecord Label Executive (uncredited)
Vinny DeGennaroBouncer (uncredited)
Lamman RuckerMan on Couch at Radio Station (uncredited)- Erica IseBridesmaid (uncredited)
Spencer KaydenBridesmaid (uncredited)
Joanie LaurerWoman at Party (uncredited)- Brother Eden DouglasPark Chess Player #1 (uncredited)
