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John CusackJonathan Trager
Kate BeckinsaleSara Thomas
Jeremy PivenDean Kansky
Bridget MoynahanHalley Buchanan
John CorbettLars Hammond
Molly ShannonEve
Eugene LevyBloomingdale's Salesman
Lilli LavineBloomingdale's Stock Girl- Michael Guarino, Jr.Customer at Bloomingdale's
Abdul AlshawishCustomer at Bloomingdale's
Stephen BruceHost at Serendipity
David SparrowJosh's Dad
Gary GerbrandtJosh
Ann TalmanBloomingdale's Saleswoman #1
Crystal BockBloomingdale's Saleswoman #2
Kate BlumbergCourtney Kansky- Ron PayneLouis Trager
Marcia BennettMrs. Louis Trager
Eve CrawfordMrs. Buchanan
Victor A. YoungMr. Buchanan
Leo FitzpatrickLeasing Office Temp
Evan NeumannKenny
Lucy GordonCaroline Mitchell
Kevin RiceKip
Brenda LoganHair Stylist
James GoodwinNick Roberts
John Ellison ConleeArtie
Charles A. GarganoAnnouncer At Golf Range
Arthur PascuzziGolf Instructor
Mike BenitezSuperintendent
Christopher James BakerLars Band #1
Neil ClaxtonLars Band #2
Sandra CaldwellPR Woman
Ajay MehtaPakistani Cab Driver
Clark MiddletonAirport Cab Driver
Marqus BobesichStreet Vendor
Kevin Kean MurphyMan On Street- Paul RutledgeGolf Ball Man
Simon JutrasSebastian Mignon
Pamela RedfernFlight Attendant- Aron TagerJanitor
- Catherine KuhnWedding Coordinator
Buck HenryCustomer at Bloomingdales (sem créditos)