All Cast

John Cusack

John Cusack

Jonathan Trager

Kate Beckinsale

Kate Beckinsale

Sara Thomas

Jeremy Piven

Jeremy Piven

Dean Kansky

Bridget Moynahan

Bridget Moynahan

Halley Buchanan

John Corbett

John Corbett

Lars Hammond

Molly Shannon

Molly Shannon

Eve

Eugene Levy

Eugene Levy

Bloomingdale's Salesman

Lilli Lavine

Lilli Lavine

Bloomingdale's Stock Girl

Michael Guarino, Jr.

Michael Guarino, Jr.

Customer at Bloomingdale's

Abdul Alshawish

Abdul Alshawish

Customer at Bloomingdale's

Stephen Bruce

Stephen Bruce

Host at Serendipity

David Sparrow

David Sparrow

Josh's Dad

Gary Gerbrandt

Gary Gerbrandt

Josh

Ann Talman

Ann Talman

Bloomingdale's Saleswoman #1

Crystal Bock

Crystal Bock

Bloomingdale's Saleswoman #2

Kate Blumberg

Kate Blumberg

Courtney Kansky

Ron Payne

Ron Payne

Louis Trager

Marcia Bennett

Marcia Bennett

Mrs. Louis Trager

Eve Crawford

Eve Crawford

Mrs. Buchanan

Victor A. Young

Victor A. Young

Mr. Buchanan

Leo Fitzpatrick

Leo Fitzpatrick

Leasing Office Temp

Evan Neumann

Evan Neumann

Kenny

Lucy Gordon

Lucy Gordon

Caroline Mitchell

Kevin Rice

Kevin Rice

Kip

Brenda Logan

Brenda Logan

Hair Stylist

James Goodwin

James Goodwin

Nick Roberts

John Ellison Conlee

John Ellison Conlee

Artie

Charles A. Gargano

Charles A. Gargano

Announcer At Golf Range

Arthur Pascuzzi

Arthur Pascuzzi

Golf Instructor

Mike Benitez

Mike Benitez

Superintendent

Christopher James Baker

Christopher James Baker

Lars Band #1

Neil Claxton

Neil Claxton

Lars Band #2

Sandra Caldwell

Sandra Caldwell

PR Woman

Ajay Mehta

Ajay Mehta

Pakistani Cab Driver

Clark Middleton

Clark Middleton

Airport Cab Driver

Marqus Bobesich

Marqus Bobesich

Street Vendor

Kevin Kean Murphy

Kevin Kean Murphy

Man On Street

Paul Rutledge

Paul Rutledge

Golf Ball Man

Simon Jutras

Simon Jutras

Sebastian Mignon

Pamela Redfern

Pamela Redfern

Flight Attendant

Aron Tager

Aron Tager

Janitor

Catherine Kuhn

Catherine Kuhn

Wedding Coordinator

Buck Henry

Buck Henry

Customer at Bloomingdales (uncredited)