Inspired by @nikkilounoel, @ladyprofessor, and @Nicholas [Just want to add that I'm kind of embarrassed about the size of my list compared to everyone else's. 😬]
  2. About Time (2013)
  3. Almost Famous (2000)
  4. Breakfast at Tiffany's (1961)
  5. Charade (1963)
  6. Father of the Bride (1991)
    I've been known to watch this twice in the same day. I mean that's mostly because I was too lazy to get up and get the remote but it's still good enough to watch twice.
  7. Father of the Bride Part II (1995)
  8. Funny Face (1957)
  9. How to Marry a Millionaire (1953)
  10. A League of Their Own (1992)
    My brother loves to text me late at night to tell me this is on because he knows I'll end up watching it.
  11. Mermaids (1990)
  12. Ninotchka (1939)
    I usually end up watching this one on Greta Garbo's birthday.
  13. The Philadelphia Story (1940)
  14. The Shop Around the Corner (1940)/You've Got Mail (1998)
    When I watch one, I always watch the other.
  15. the entire Star Wars saga (1977-2015)
  16. The Princess Bride (1987)
  17. To Have and Have Not (1944)
  18. Top Hat (1935)
  20. The Addams Family (1991)
  21. Addams Family Values (1993)
  22. Beetlejuice (1988)
  23. Tim Burton's Corpse Bride (2005)
  24. Dead Poet's Society (1989)
  25. Frankenweenie (2012)
  26. Good Will Hunting (1997)
  27. Hocus Pocus (1993)
  28. The Nightmare Before Christmas (1993)
    I'll also watch this around Christmas.
  29. The Sound of Music (1965)
    One of the TV stations used to show this on Thanksgiving night so now it's just become tradition to watch it then.
  30. Young Frankenstein (1974)
  32. The Bishop's Wife (1947)
  33. The Breakfast Club (1985)
    We share a birthday (although it's four years older than I am) so I usually end up watching it around then.
  34. It's a Wonderful Life (1946)
  35. Miracle on 34th Street (1947)
  36. Rise of the Guardians (2012)
  37. When Harry Met Sally... (1989)
    While I never turn down an opportunity to watch this one, it's kind of become a tradition to watch it on New Year's Eve.
  38. White Christmas (1954)