Risa Bramon Garcia Director Ben Affleck Bartender Actor Casey Affleck Tom Actor Dave Chappelle Disco Cabbie Actor Guillermo Díaz Dave Actor Angela Featherstone Caitlyn Actor Janeane Garofalo Ellie Actor Gaby Hoffmann Stephie Actor Kate Hudson Cindy Actor Catherine Kellner Hillary Actor Courtney Love Lucy Actor Brian McCardie Eric Actor Jay Mohr Jack Actor Nicole Ari Parker Bridget Actor Martha Plimpton Monica Actor Christina Ricci Val Actor Paul Rudd Kevin Actor Elvis Costello Self Kiran Merchant Restaurant Owner Actor Patrick Frederic Tiki Sobbing Man Actor Caleb Carr Cynical Bar Patron Actor James F. Murphy Drag Queen Actor Jen Albano Cheryl Actor Morgan Brown French Rocker Actor David Johansen Tiki Bartender Actor Jenni Blong Cheryl's Friend Actor Patricia Wible Ace Bar Patron Actor Shana Larsen Screenwriter Betsy Beers Producer David Gale Producer Van Toffler Producer Alan Greenspan Executive Producer Tom Rosenberg Executive Producer Sigurjon Sighvatsson Executive Producer Frank Prinzi Cinematographer Lisa Zeno Churgin Film Editing Mark Mothersbaugh Original Music Robert Mothersbaugh Original Music Ina Mayhew Production Design Judy Rhee Art Director Paul Weathered Set Decoration Susan Lyall Costume Design Deborah Aquila Casting Sarah Halley Finn Casting