Top Billed Cast

1. 

   John Cusack

   Jonathan Trager

2. 

   Kate Beckinsale

   Sara Thomas

3. 

   Jeremy Piven

   Dean Kansky

4. 

   Bridget Moynahan

   Halley Buchanan

5. 

   John Corbett

   Lars Hammond

6. 

   Molly Shannon

   Eve

7. 

   Eugene Levy

   Bloomingdale's Salesman

8. 

   Lilli Lavine

   Bloomingdale's Stock Girl

9. 

   Michael Guarino, Jr.

   Customer at Bloomingdale's

10. 

    Abdul Alshawish

    Customer at Bloomingdale's

11. 

    Stephen Bruce

    Host at Serendipity

12. 

    David Sparrow

    Josh's Dad

13. 

    Gary Gerbrandt

    Josh

14. 

    Ann Talman

    Bloomingdale's Saleswoman #1

15. 

    Crystal Bock

    Bloomingdale's Saleswoman #2

16. 

    Kate Blumberg

    Courtney Kansky

17. 

    Ron Payne

    Louis Trager

18. 

    Marcia Bennett

    Mrs. Louis Trager

19. 

    Eve Crawford

    Mrs. Buchanan

20. 

    Victor A. Young

    Mr. Buchanan

21. 

    Leo Fitzpatrick

    Leasing Office Temp

22. 

    Evan Neumann

    Kenny

23. 

    Lucy Gordon

    Caroline Mitchell

24. 

    Kevin Rice

    Kip

25. 

    Brenda Logan

    Hair Stylist

26. 

    James Goodwin

    Nick Roberts

27. 

    John Ellison Conlee

    Artie

28. 

    Charles A. Gargano

    Announcer At Golf Range

29. 

    Arthur Pascuzzi

    Golf Instructor

30. 

    Mike Benitez

    Superintendent

31. 

    Christopher James Baker

    Lars Band #1

32. 

    Neil Claxton

    Lars Band #2

33. 

    Sandra Caldwell

    PR Woman

34. 

    Ajay Mehta

    Pakistani Cab Driver

35. 

    Clark Middleton

    Airport Cab Driver

36. 

    Marqus Bobesich

    Street Vendor

37. 

    Kevin Kean Murphy

    Man On Street

38. 

    Paul Rutledge

    Golf Ball Man

39. 

    Simon Jutras

    Sebastian Mignon

40. 

    Pamela Redfern

    Flight Attendant

41. 

    Aron Tager

    Janitor

42. 

    Catherine Kuhn

    Wedding Coordinator

43. 

    Buck Henry

    Customer at Bloomingdales (uncredited)