84 minutes
11/8/1991
Waymon has a great job in real estate and a promising future, but he's also trapped in a loveless longterm relationship. He meets Natalie, a beautiful club-hopping hipster, and quickly falls in love. Realizing he's just not cool enough to attract her on his own, he seeks the help of his friend Bobby, a free-spirited smooth talker who works in the mail room at Waymon's firm and utilizes the predicament as leverage to advance in the company.
Joseph C. Phillips
as Waymon
Halle Berry
as Natalie
Tommy Davidson
as Bobby
Anne-Marie Johnson
as Diedre
Samuel L. Jackson
as Monroe
Kim Coles
as Millicent
Sam Rockwell
as Gary
Denis Leary
as Jake
David Marshall Grant
as David
Jon Cypher
as Drake
James McDaniel
as Roland Halloran
Joe Torry
as Darryl
Isaiah Washington
as Hustler
Novella Nelson
as Olivia
Kevin Hooks
as Married Man
Ellen Cleghorne
as Cocktail Waitress
Annie Golden
as Sheila
Paul Butler
as Leroy Halloran
Ira Wheeler
as Mr. Atwell
Jodeci
as Band at Lola's
Susan Haskell
as Donna