Ben Affleck

Bartender

Casey Affleck

Tom

Dave Chappelle

Disco Cabbie

Guillermo Díaz

Dave

Angela Featherstone

Caitlyn

Janeane Garofalo

Ellie

Gaby Hoffmann

Stephie

Kate Hudson

Cindy

Catherine Kellner

Hillary

Courtney Love

Lucy

Brian McCardie

Eric

Jay Mohr

Jack

Nicole Ari Parker

Bridget

Martha Plimpton

Monica

Christina Ricci

Val

Paul Rudd

Kevin

Jenni Blong

Cheryl's Friend

Elvis Costello

Self

David Johansen

Tiki Bartender

Kiran Merchant

Restaurant Owner

Brian Berrebbi

Punk at Bar (uncredited)

Alice Dinnean

Cheryl's Woman (uncredited)

Ariane Von Kamp

Rocker Girl (uncredited)

Kathy Searle

Restaurant Patron (uncredited)

Nick Stellate

Drunk Biker (uncredited)