Trailer
Cast
Victor A. Young
Mr. Buchanan
Eugene Levy
Bloomingdale's Salesman
Lucy Gordon
Caroline Mitchell
Ajay Mehta
Pakistani Cab Driver
Marqus Bobesich
Street Vendor
John Corbett
Lars Hammond
John Ellison Conlee
Artie
T. Scott Cunningham
Ryan
Jeremy Piven
Dean Kansky
Kate Blumberg
Courtney Kansky
Arthur Pascuzzi
Golf Instructor
Neil Claxton
Lars Band #2
Clark Middleton
Airport Cab Driver
Simon Jutras
Sebastian Mignon
Charles A. Gargano
Announcer At Golf Range
Mike Benitez
Superintendent
Crystal Bock
Bloomingdale's Saleswoman #2
Evan Neumann
Kenny
Lilli Lavine
Bloomingdale's Stock Girl
Abdul Alshawish
Customer at Bloomingdale's
Kate Beckinsale
Sara Thomas
Bridget Moynahan
Halley Buchanan
Stephen Bruce
Host at Serendipity
Ann Talman
Bloomingdale's Saleswoman #1
Molly Shannon
Eve
David Sparrow
Josh's Dad
James Goodwin
Nick Roberts
Brenda Logan
Hair Stylist
Sandra Caldwell
PR Woman
John Cusack
Jonathan Trager
Eve Crawford
Mrs. Buchanan
Leo Fitzpatrick
Leasing Office Temp
Gary Gerbrandt
Josh
Kevin Rice
Kip
Kevin Kean Murphy
Man On Street
Pamela Redfern
Flight Attendant
Aron Tager
Janitor
Marcia Bennett
Mrs. Louis Trager
Christopher James Baker
Lars Band #1
Paul Rutledge
Golf Ball Man
Buck Henry
Customer at Bloomingdales (uncredited)