Adrien Brody as Chris Calloway

Elise Neal as Jeanine

Lauryn Hill as Leslie

David Moscow as Reggae

Simon Baker as Kenny

Catherine Kellner as Nancy

Malcolm-Jamal Warner as Steven

Jesse L. Martin as Quincy

Sybil Darrow as Lenore

John Carroll Lynch as John English

Vonte Sweet as Marcus

Michael Stoyanov as Ethan

Elon Gold as Kurt

Lori Heuring as Donna

Avery Kidd Waddell as Al-Tarique

Roger Anthony as Sanchez

Gwendolyn Bailey as Erica

Tai Bennett as Anthony

Robert Capelli Jr. as Mike D'Amato

Siena Goines as Carol

Jennifer Coolidge as Woman at McClure's

Rachel Zients as Woman at McClure's

Gwendolyn Bessette as Woman at McClure's

H.M. Coakley as Club Announcer

Matthew Black as Waiter

Ivan Bodley as Bass Player

Jeff Bond as Drunken Frat Boy

Damien Bosco as Wedding Guest

Karey Butterworth as Girl at Bar

Ken Elston as Waiter

Nicholas Giordano as Frank

Katie Hammel as Maid of Honor

David Horton as Restaurant Patron

Jennifer Jiles as Upscale Patron's Wife

Lord Kayson as Drug Dealer Chaos

Lauren Patrice Nadler as Casting Director

Joey Napoli as Frat Guy

Geneva Carr as Funeral Guest (uncredited)

Bill Golodner as Party Goer (uncredited)

Zoe Hunter as Theatregoer (uncredited)

Rod Maiorano as Happy Wedding Guest (uncredited)

Shana Stein as Margaret (uncredited)