Ben Affleck as Bartender

Casey Affleck as Tom

Dave Chappelle as Disco Cabbie

Guillermo Díaz as Dave

Angela Featherstone as Caitlyn

Janeane Garofalo as Ellie

Gaby Hoffmann as Stephie

Kate Hudson as Cindy

Catherine Kellner as Hillary

Courtney Love as Lucy

Brian McCardie as Eric

Jay Mohr as Jack

Nicole Ari Parker as Bridget

Martha Plimpton as Monica

Christina Ricci as Val

Paul Rudd as Kevin

Jennifer Albano as Cheryl

Jenni Blong as Cheryl's Friend

Morgan Brown as French Rocker

Caleb Carr as Cynical Bar Patron

Elvis Costello as Self

Patrick Frederic as Tiki Sobbing Man

David Johansen as Tiki Bartender

Kiran Merchant as Restaurant Owner

James F. Murphy as Drag Queen

Patricia Wible as Ace Bar Patron

Brian Berrebbi as Punk at Bar (uncredited)

Jamie Bonelli as Punk Dancer (uncredited)

Stephanie Dale as Cheryl's Friend (uncredited)

Alice Dinnean as Cheryl's Woman (uncredited)

Kelly Ebsary as Cheryl's Friend (uncredited)

Alexis Fleisig as Bar Band (uncredited)

Eli Janney as Bar Band (uncredited)

Ariane Von Kamp as Rocker Girl (uncredited)

Scott McCloud as Bar Band (uncredited)

Seamus McNally as Crazed Driver (uncredited)

Michael J. Meyers as Drunken Yuppie (uncredited)

Kathy Searle as Restaurant Patron (uncredited)

Nick Stellate as Drunk Biker (uncredited)

Oriana Nicole Tavoularis as Rocker Girl (uncredited)

Johnny Temple as Bar Band (uncredited)

Stephen Vause as Bar Patron (uncredited)