
Sidney and Dre can attribute their lifelong friendship and the launch of their careers to one single childhood instant... witnessing the birth of hip-hop on a New York street corner. Now some 15 years later, she is a revered music critic at a national magazine and he is a successful, though unfulfilled, hip-hop record company executive. Both come to realize that their true life passions will only be fulfilled by remembering what they learned that day on the corner.

Sidney 'Sid' Shaw

Andre Romulus 'Dre' Ellis

Chris Anton 'Cav' Vichon

Reese Marie Wiggam Ellis

Kelby Dawson

Francine

Simon

Ren
Ten
Meghan
Young Sidney

Young Dre

Self (Radio DJ)

Trish Hofmann
Richard Lawson

Older Woman
Woman

Woman 2

Woman 3
Bartender 1

Co-Worker
Host
Hot 97 Assistant
Instructor
Iridium Waiter

Self

Self - Black Thought [The Roots]

Self

Self

Reverend
Bartender

Sidney's LA Assistant

Crafts Vendor

Self

Self

Self

Self
Self
Self - Trugoy the Dove [De La Soul]

Self - Posdnuos [De La Soul]

Self - Maseo [De La Soul]

Self

Self

Self

Self

Self

Self
Backstage Bartender
Kid in the Park

Hot 97 Receptionist

Royale (uncredited)

Record Label Executive (uncredited)

Bouncer (uncredited)

Man on Couch at Radio Station (uncredited)
Bridesmaid (uncredited)

Bridesmaid (uncredited)

Woman at Party (uncredited)