Alec Baldwin

Character: Bob Berrenger

Philip Seymour Hoffman

Character: Joseph Turner White

Charles Durning

Character: Mayor George Bailey

Clark Gregg

Character: Doug Mackenzie

Patti LuPone

Character: Sherry Bailey

William H. Macy

Character: Walt Price

Sarah Jessica Parker

Character: Claire Wellesley

David Paymer

Character: Marty Rossen

Julia Stiles

Character: Carla

Rebecca Pidgeon

Character: Ann

Jim Frangione

Character: Tommy Max

Vincent Guastaferro

Character: Uberto Pazzi-Sforzo

Michael Higgins

Character: Doc Wilson

Ricky Jay

Character: Jack

Lionel Mark Smith

Character: Bill Smith

Matt Malloy

Character: Hotel Clerk

Christopher Kaldor

Character: Officer Cal Thompkin

Michael Bradshaw

Character: Priest

Morris Lamore

Character: Bunky

Allen Soule

Character: Spud

Tony V.

Character: Water Delivery Man

Tony Mamet

Character: Electrician

Jack Wallace

Character: Bellhop

Michael James O'Boyle

Character: Chuckie

Charlotte Potok

Character: Maude

Frederic Levy

Character: Gun Store Owner

J.J. Johnston

Character: Stationmaster

Richard L. Friedman

Character: Postman

Kolbie McCabe

Character: Girl on Scooter

Emma Norman

Character: Fisherwoman

Dee Nelson

Character: Decorator

Brian Howe

Character: Bartender

Robert E. Walsh

Character: Trooper #1

G. Roy Levin

Character: Salesman with Rubber Duck

Matthew Pidgeon

Character: B.B.G. TV Reporter

Danny Hovanesian

Character: Bailiff

Jerry Graff

Character: Fake Judge

Timothy Jernigan-Smith

Character: Billy on Bike

Paul Butler

Character: Real Judge

Alexandra Kerry

Character: Television Director

Ken Cheeseman

Character: Trooper #2

Jordan Lage

Character: Doc Morten

Linda Kimbrough

Character: Courteney

Lana Bilzerian

Character: Girl PA

Laura Silverman

Character: Secretary

Josh Marchette

Character: Production Assistant

Jonathan Katz

Character: Howie Gold

Sean Patrick Reilly

Character: Loop

Chris De Christopher

Character: Painter 1 (uncredited)

Darrell Geer

Character: Vermont State Trooper (uncredited)

John Krasinski

Character: Judge's Assistant (uncredited)

David Lauren

Character: News Producer (uncredited)

Cindy Lentol

Character: Reporter (uncredited)

Kevin Foster McCarthy

Character: Airport Van Driver (uncredited)

Todd Poudrier

Character: Production Assistant (uncredited)

Alan Francis Sullivan

Character: Vermont State Trooper (uncredited)

Kate Super

Character: Production Assistant (uncredited)