Top Billed Cast

1. 

   Meg Ryan

   Kathleen Kelly

2. 

   Tom Hanks

   Joe Fox

3. 

   Greg Kinnear

   Frank Navasky

4. 

   Heather Burns

   Christina Plutzker

5. 

   Parker Posey

   Patricia Eden

6. 

   Dave Chappelle

   Kevin Jackson

7. 

   Jean Stapleton

   Birdie Conrad

8. 

   Steve Zahn

   George Pappas

9. 

   Dabney Coleman

   Nelson Fox

10. 

    John Randolph

    Schulyer Fox

11. 

    Hallee Hirsh

    Annabelle Fox

12. 

    Jeffrey Scaperrotta

    Matt Fox

13. 

    Cara Seymour

    Gillian Quinn

14. 

    Katie Finneran

    Maureen, the Nanny

15. 

    Michael Badalucco

    Charlie

16. 

    Deborah Rush

    Veronica Cash

17. 

    Veanne Cox

    Miranda Margulies

18. 

    Bruce Jay Friedman

    Vince Mancini

19. 

    Sara Ramirez

    Rose, Zabars Cashier

20. 

    Howard Spiegel

    Henry, Zabars Shopper

21. 

    Diane Sokolow

    Zabars Shopper

22. 

    Julie Kass

    Zabars Shopper

23. 

    Reiko Aylesworth

    Thanksgiving Guest

24. 

    Katie Sagona

    Young Kathleen Kelly

25. 

    Kathryn Meisle

    Cecilia Kelly

26. 

    Nina Zoie Lam

    T.V. Reporter

27. 

    Maggie Murphy

    Theater Patron

28. 

    Michelle Blakely

    Shopper

29. 

    Meredith White

    Shopper

30. 

    Dianne Dreyer

    Shopper

31. 

    Julie Galdieri

    Shopper

32. 

    Leila Nichols

    Shopper

33. 

    Mary A. Kelly

    Fox Books Shopper

34. 

    Chris Messina

    Fox Salesperson

35. 

    Ronobir Lahiri

    Man at Cafe Lalo

36. 

    André Sogliuzzo

    Waiter at Lalo

37. 

    Peter A. Mian

    Capeman

38. 

    Richard Cohen

    Starbucks Customer

39. 

    Enzo Angileri

    Starbucks Customer

40. 

    Nick Brown

    Juggler

41. 

    Ann Fleuchaus

    Sarah Mancini

42. 

    Neil Bonin

    Party Guest

43. 

    Bill McHugh

    Party Guest

44. 

    Santiago Quinones

    Decorator

45. 

    Lynn Grossman

    Yvette Fox

46. 

    Dolores Sirianni

    Mother of Twins

47. 

    Nicole Bernadette

    Florist

48. 

    Jane Adams

    Sydney Anne (uncredited)

49. 

    Cecelia Antoinette

    Restaurant Patron (uncredited)

50. 

    Elwood Edwards

    Online 'You've Got Mail' Voice (voice) (uncredited)

51. 

    Alfonso Gomez-Rejon

    Party Guest (uncredited)

52. 

    Gideon Jacobs

    Young Joe Fox (uncredited)

53. 

    Brick Mason

    Man Letting Joe Fox in (uncredited)

54. 

    Scott Mullin

    Male Runner (uncredited)

55. 

    Logan Steinhardt

    Kid in Bookstore (uncredited)

56. 

    Anthony Welch

    Business Executive (uncredited)