Alec Baldwin

as Bob Berrenger

Born 04/03/1958, age

Philip Seymour Hoffman

as Joseph Turner White

Born 07/23/1967

Died 02/02/2014, age

Charles Durning

as Mayor George Bailey

Born 02/28/1923

Died 12/24/2012, age

Clark Gregg

as Doug Mackenzie

Born 04/02/1962, age

Patti LuPone

as Sherry Bailey

Born 04/21/1949, age

William H. Macy

as Walt Price

Born 03/13/1950, age

Sarah Jessica Parker

as Claire Wellesley

Born 03/25/1965, age

David Paymer

as Marty Rossen

Born 08/30/1954, age

Julia Stiles

as Carla

Born 03/28/1981, age

Rebecca Pidgeon

as Ann

Born 10/10/1965, age

Vincent Guastaferro

as Uberto Pazzi-Sforzo

Born 04/06/1950, age

Ricky Jay

as Jack

Born 06/26/1946

Died 11/24/2018, age

Lionel Mark Smith

as Bill Smith

Born 02/05/1946

Died 02/13/2008, age

Matt Malloy

as Hotel Clerk

Born 01/12/1963, age

Jack Wallace

as Bellhop

Born 08/10/1933

Died 04/16/2020, age

J.J. Johnston

as Stationmaster

Born 10/24/1933, age

Brian Howe

as Bartender

Born 12/31/1957, age

Paul Butler

as Real Judge

Born 03/12/1942

Died 01/12/2010, age

John Krasinski

as Judge's Assistant (uncredited)

Born 10/20/1979, age