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. 😬]
  1. ANYTIME:
  2. About Time (2013)
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  3. Almost Famous (2000)
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  4. Breakfast at Tiffany's (1961)
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  5. Charade (1963)
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  6. Father of the Bride (1991)
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    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)
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  8. Funny Face (1957)
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  9. How to Marry a Millionaire (1953)
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  10. A League of Their Own (1992)
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    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)
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  12. Ninotchka (1939)
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    I usually end up watching this one on Greta Garbo's birthday.
  13. The Philadelphia Story (1940)
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  14. The Shop Around the Corner (1940)/You've Got Mail (1998)
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    When I watch one, I always watch the other.
  15. the entire Star Wars saga (1977-2015)
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  16. The Princess Bride (1987)
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  17. To Have and Have Not (1944)
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  18. Top Hat (1935)
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  19. FALL STAPLES:
  20. The Addams Family (1991)
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  21. Addams Family Values (1993)
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  22. Beetlejuice (1988)
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  23. Tim Burton's Corpse Bride (2005)
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  24. Dead Poet's Society (1989)
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  25. Frankenweenie (2012)
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  26. Good Will Hunting (1997)
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  27. Hocus Pocus (1993)
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  28. The Nightmare Before Christmas (1993)
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    I'll also watch this around Christmas.
  29. The Sound of Music (1965)
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    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)
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  31. WINTER STAPLES:
  32. The Bishop's Wife (1947)
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  33. The Breakfast Club (1985)
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    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)
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  35. Miracle on 34th Street (1947)
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  36. Rise of the Guardians (2012)
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  37. When Harry Met Sally... (1989)
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    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)
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