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

Gretchen

Stephanie Sanditz

Roebling

Andrew Jack

Photographer

Stan Tracy

Miss Tree

Kristen Schaal

Executive No. 1

John Rothman

Policewoman

Viola Davis

Barry

William Sanford

Counterman (Uncredited)

Domenick Lombardozzi

Gracy

Arthur J. Nascarella

Sanitation Worker

Ray Seiden

Passerby

Robert Ray Manning Jr.

TV Newscaster

Roma Torre

Clara (uncredited)

Andrea Barnes

Hector

Cole Hawkins

Nurse Ester

Ebony Jo-Ann

Irate Director Richard (uncredited)

James Mangold

Limo Driver

Bill Corsair

Doorman at Party

Kevin Daniels

2nd Studio Executive (uncredited)

David Aaron Baker

Faux Wolfgang

Jonathan Fried

Faux Emeril

Francis Dumaurier

Actor in Advertisement (uncredited)

Craig Bierko

Passerby

Robert Manning

CRG Intern

Stephanie Montalvo

Assistant Director

George Hahn

Cameraman

Joseph Mosso

Carriage Driver

Cornelius Byrne

Purse Thief

Chazz Menendez

Dennis

Brandon Parrish

Monica

Ginger Britt Daniels

Office Woman

Martha Madison

Rooftop Violinist

Nai Yuan Hu

Cameraman

Joe Mosso

Distinguished Actor

Michael Shelle

Commercial Director

Matt Beisner

Monica

Brittney Startzman

Executive No. 2

Dennis Rees

Executive No. 3

Michael Cassady

Ad Executive

Brian Letscher

Executive's Wife

Meg Gibson

Commercial Director

Matthew Beisner

Bridge Cop

Russell Di Perna

1876 Doorman

Frank Arcuri

Marty (uncredited)

Del Pentecost

Cab Driver

Henry Doyle

Woman in Movie (uncredited)

Shalom Harlow

Hospital Orderly (uncredited)

Eddie Marrero

Bartender (uncredited)

Todd Poudrier

Leopold's Maid (uncredited)

Jorjeana Marie

Prospective Fiancée (uncredited)

Diana Brownstone

Prospective Fiancée (uncredited)

Peggy Flood

Carriage Driver

Cornelius Patrick Byrne