Kate McKay

Meg Ryan

Leopold

Hugh Jackman

Stuart

Liev Schreiber

Charlie McKay

Breckin Meyer

Darci

Natasha Lyonne

J.J. Camden

Bradley Whitford

Uncle Millard

Paxton Whitehead

Dr. Geisler

Spalding Gray

Colleague Bob

Josh Stamberg

Otis

Philip Bosco

Ad Executive Phil

Matthew Sussman

Patrice

Charlotte Ayanna

Roebling

Andrew Jack

Photographer

Stan Tracy

Miss Tree

Kristen Schaal

Executive No. 1

John Rothman

Policewoman

Viola Davis

Counterman (Uncredited)

Domenick Lombardozzi

Sanitation Worker

Ray Seiden

Clara

Andrea Barnes

Hector

Cole Hawkins

Nurse Ester

Ebony Jo-Ann

Movie Director

James Mangold

Limo Driver

Bill Corsair

Barry

William Sanford

Doorman at Party

Kevin Daniels

Studio Executive

David Aaron Baker

Actor in Advertisement

Craig Bierko

Gracy

Arthur Nascarella

Passerby

Robert Manning

TV Newscaster

Roma Torre

Faux Wolfgang

Jonathan Fried

Faux Emeril

Francis Dumaurier

CRG Intern

Stephanie Montalvo

Assistant Director

George Hahn

Cameraman

Joe Mosso

Carriage Driver

Cornelius Byrne

Purse Thief

Chazz Menendez

Dennis

Brandon Parrish

Monica

Brittney Startzman

Office Woman

Martha Madison

Gretchen

Stephanie Sanditz

Rooftop Violinist

Nai Yuan Hu

Distinguished Actor

Michael Shelle

Commercial Director

Matthew Beisner

Executive No. 2

Dennis Rees

Executive No. 3

Michael Cassady

Ad Executive

Brian Letscher

Executive's Wife

Meg Gibson

Cab Driver

Henry Doyle

Bridge Cop

Russell Di Perna

1876 Doorman

Frank Arcuri

Passerby

Robert Ray Manning Jr.

Cameraman

Joseph Mosso

Carriage Driver

Cornelius Patrick Byrne

Director

James Mangold