Timothy Hutton

Willie Conway

Matt Dillon

Tommy "Birdman" Rowland

Noah Emmerich

Michael "Mo" Morris

Annabeth Gish

Tracy Stover

Lauren Holly

Darian Smalls

Uma Thurman

Andera

Mira Sorvino

Sharon Cassidy

Michael Rapaport

Paul Kirkwood

Rosie O'Donnell

Gina Barrisano

Pruitt Taylor Vince

Stanley "Stinky" Womack

Max Perlich

Kev

Martha Plimpton

Jan

Natalie Portman

Marty

Anne Bobby

Sarah Morris

Richard Bright

Dick Conway

Sam Robards

Steve Rossmore

David Arquette

Bobby Conway

Adam LeFevre

Victor

John Carroll Lynch

Frank Womack

Tom Gibis

Peter the Eater

Greg Dulli

Lead Singer, Afghan Whigs

John Scurti

Ticket Agent

Frank Anello

Irv

Camille D'Ambrose

Sharon's Mother

Sarah Katz

Kristen Rossmore

Martin Ruben

Chip

Allison Levine

Waitress at Moonlight Mile

Earl R. Burt

Bartender

Trent Nicholas Thompson

Michael Morris, Jr.

Nicole Ranallo

Cheryl Morris

Joyce Lacey

Reunion Classmate #1

Anne W. Erickson

Coffee Shop Waitress

Oliver Osterberg

Drinker #1

Sterling Robson

Drinker #2

Herbie Ade

Bar Owner

Tammara Melloy

Bowler (uncredited)

Lori J. Ness

Woman on the Street (uncredited)

Rachel Oliva

High School Alumna (uncredited)

Tomas Settell

Male Nurse (uncredited)