Meg Ryan

Kate McKay

Hugh Jackman

Leopold

Liev Schreiber

Stuart Besser

Breckin Meyer

Charlie McKay

Natasha Lyonne

Darci

Bradley Whitford

J.J. Camden

Paxton Whitehead

Uncle Millard

Spalding Gray

Dr. Geisler

Josh Stamberg

Colleague Bob

Matthew Sussman

Ad Executive Phil

Philip Bosco

Otis

Charlotte Ayanna

Patrice

Andrew Jack

Roebling

Kristen Schaal

Miss Tree

Arthur J. Nascarella

Gracy

Robert Ray Manning Jr.

Passerby

Roma Torre

TV Newscaster

Viola Davis

Policewoman

Jonathan Fried

Faux Wolfgang

Francis Dumaurier

Faux Emeril

Cole Hawkins

Hector

Ebony Jo-Ann

Nurse Ester

George Hahn

Assistant Director

Chazz Menendez

Purse Thief

Ginger Britt Daniels

Monica

Martha Madison

Office Woman

Matt Beisner

Commercial Director

John Rothman

Executive #1

Brian Letscher

Ad Executive

Meg Gibson

Executive's Wife

Kevin Daniels

Doorman at Party

Del Pentecost

Marty (uncredited)

Domenick Lombardozzi

Counterman (Uncredited)

Craig Bierko

Actor in Advertisement (uncredited)

James Mangold

Irate Director Richard (uncredited)

David Aaron Baker

2nd Studio Executive (uncredited)

Shalom Harlow

Woman in Movie (uncredited)

Jorjeana Marie

Leopold's Maid (uncredited)

Diana Brownstone

Prospective Fiancée (uncredited)

Peggy Flood

Prospective Fiancée (uncredited)