During a snowy winter in the small fictional town of Knight's Ridge, Massachusetts, a group of lifelong buddies hang out, drink and struggle to connect with the women who affect their decisions, dreams and desires.
Willie Conway
Timothy Hutton
Tommy "Birdman" Rowland
Matt Dillon
Michael "Mo" Morris
Noah Emmerich
Tracy Stover
Annabeth Gish
Darian Smalls
Lauren Holly
Andera
Uma Thurman
Sharon Cassidy
Mira Sorvino
Paul Kirkwood
Michael Rapaport
Gina Barrisano
Rosie O'Donnell
Stanley "Stinky" Womack
Pruitt Taylor Vince
Kev
Max Perlich
Jan
Martha Plimpton
Marty
Natalie Portman
Sarah Morris
Anne Bobby
Dick Conway
Richard Bright
Steve Rossmore
Sam Robards
Bobby Conway
David Arquette
Victor
Adam LeFevre
Frank Womack
John Carroll Lynch
Peter the Eater
Tom Gibis
Lead Singer, Afghan Whigs
Greg Dulli
Ticket Agent
John Scurti
Irv
Frank Anello
Sharon's Mother
Camille D'Ambrose
Kristen Rossmore
Sarah Katz
Chip
Martin Ruben
Waitress at Moonlight Mile
Allison Levine
Bartender
Earl R. Burt
Michael Morris, Jr.
Trent Nicholas Thompson
Cheryl Morris
Nicole Ranallo
Reunion Classmate #1
Joyce Lacey
Coffee Shop Waitress
Anne W. Erickson
Drinker #1
Oliver Osterberg
Drinker #2
Sterling Robson
Bar Owner
Herbie Ade
Bowler (uncredited)
Tammara Melloy
High School Alumna (uncredited)
Rachel Oliva
Male Nurse (uncredited)
Tomas Settell