Welcome to Collinwood

William H. Macy

Riley

Isaiah Washington

Leon

Sam Rockwell

Pero

Michael Jeter

Toto

Luis Guzmán

Cosimo

John Buck Jr.

Old Man in Prison

Patricia Clarkson

Rosalind

Andy Davoli

Basil

Brett C. Leonard

Mickey

Frank O'Donnell

Priest

Peter Veneziano

Referee

Bernard Canepari

Judge

Art Oughton

Corrections Officer

Ray Calabrese

Oswald

George Clooney

Jerzy

Annie Kitral

Nun #1

Lissy Gulick

Nun #2

Dorothy Silver

Nun #3

Maryanne Nagel

Mrs. Antwerp

David Warshofsky

Babitch

Jennifer Esposito

Carmela

Gabrielle Union

Michelle

Don Kost

Beddo

June Lang

Old Purse Woman

Basil Russo

Funeral Home Director

Angela Russo-Otstot

Arguing Woman

Wayne S. Turney

Arguing Man

Rohn Thomas

Janitor

Ann Russo

Colleen (uncredited)

Blaine Pate

Cosimo's Lawyer (uncredited)

Danny Lentz

Bailiff