Timothy Hutton as Willie Conway

Matt Dillon as Tommy "Birdman" Rowland

Noah Emmerich as Michael "Mo" Morris

Annabeth Gish as Tracy Stover

Lauren Holly as Darian Smalls

Uma Thurman as Andera

Mira Sorvino as Sharon Cassidy

Michael Rapaport as Paul Kirkwood

Rosie O'Donnell as Gina Barrisano

Pruitt Taylor Vince as Stanley "Stinky" Womack

Max Perlich as Kev

Martha Plimpton as Jan

Natalie Portman as Marty

Anne Bobby as Sarah Morris

Richard Bright as Dick Conway

Sam Robards as Steve Rossmore

David Arquette as Bobby Conway

Adam LeFevre as Victor

John Carroll Lynch as Frank Womack

Tom Gibis as Peter the Eater

Greg Dulli as Lead Singer, Afghan Whigs

John Scurti as Ticket Agent

Frank Anello as Irv

Camille D'Ambrose as Sharon's Mother

Sarah Katz as Kristen Rossmore

Martin Ruben as Chip

Allison Levine as Waitress at Moonlight Mile

Earl R. Burt as Bartender

Trent Nicholas Thompson as Michael Morris, Jr.

Nicole Ranallo as Cheryl Morris

Joyce Lacey as Reunion Classmate #1

Anne W. Erickson as Coffee Shop Waitress

Oliver Osterberg as Drinker #1

Sterling Robson as Drinker #2

Herbie Ade as Bar Owner

Tammara Melloy as Bowler (uncredited)

Lori J. Ness as Woman on the Street (uncredited)

Rachel Oliva as High School Alumna (uncredited)

Tomas Settell as Male Nurse (uncredited)