Meg Ryan as Kate McKay

Hugh Jackman as Leopold

Liev Schreiber as Stuart Besser

Breckin Meyer as Charlie McKay

Natasha Lyonne as Darci

Bradley Whitford as J.J. Camden

Paxton Whitehead as Uncle Millard

Spalding Gray as Dr. Geisler

Josh Stamberg as Colleague Bob

Matthew Sussman as Ad Executive Phil

Philip Bosco as Otis

Stephanie Sanditz as Gretchen

Charlotte Ayanna as Patrice

Andrew Jack as Roebling

Stan Tracy as Photographer

Kristen Schaal as Miss Tree

William Sanford as Barry

Arthur J. Nascarella as Gracy

Robert Ray Manning Jr. as Passerby

Roma Torre as TV Newscaster

Viola Davis as Policewoman

Ray Seiden as Sanitation Worker

Jonathan Fried as Faux Wolfgang

Francis Dumaurier as Faux Emeril

Cole Hawkins as Hector

Stephanie Montalvo as CRG Intern

Ebony Jo-Ann as Nurse Ester

George Hahn as Assistant Director

Joseph Mosso as Cameraman

Cornelius Byrne as Carriage Driver

Chazz Menendez as Purse Thief

Brandon Parrish as Dennis

Ginger Britt Daniels as Monica

Martha Madison as Office Woman

Nai Yuan Hu as Rooftop Violinist

Michael Shelle as Distinguished Actor

Matt Beisner as Commercial Director

Bill Corsair as Limo Driver

John Rothman as Executive #1

Dennis Rees as Executive #2

Michael Cassady as Executive #3

Brian Letscher as Ad Executive

Meg Gibson as Executive's Wife

Kevin Daniels as Doorman at Party

Henry Boyle as Cab Driver

Russell Di Perna as Bridge Cop

Frank Arcuri as 1876 Doorman

Andrea Barnes as Clara (uncredited)

Del Pentecost as Marty (uncredited)

Domenick Lombardozzi as Counterman (Uncredited)

Craig Bierko as Actor in Advertisement (uncredited)

James Mangold as Irate Director Richard (uncredited)

David Aaron Baker as 2nd Studio Executive (uncredited)

Shalom Harlow as Woman in Movie (uncredited)

Eddie Marrero as Hospital Orderly (uncredited)

Todd Poudrier as Bartender (uncredited)

Colby Ryan as Flower Shop Clerk (uncredited)

Jorjeana Marie as Leopold's Maid (uncredited)

Diana Brownstone as Prospective Fiancée (uncredited)

Peggy Flood as Prospective Fiancée (uncredited)