LogFAQs > #961153143

I rate based on overall enjoyability, festive-ness, and how well it captures the spirit of Christmas. I've managed this list since like 2018 and update it every year
Note: For ongoing TV series, I only take a max of one Christmas episode to count as a "Christmas special".

1. A Charlie Brown Christmas
2. The Polar Express
3. Twilight Zone - The Night of the Meek
4. A Christmas Carol (1999, TNT)
5. National Lampoon's Christmas Vacation
6. How The Grinch Stole Christmas (original)
7. Rudolph the Red Nosed Reindeer
8. A Christmas Story
9. A Christmas Carol (2006, Disney)
10. Garfield Family Christmas
11. Elf
12. Scrooged
13. Home Alone
14. Its a Wonderful Life
15. The Santa Clause
16. Klaus
17. A Muppets Christmas Carol
18. The Star
19. Miracle On 34th Street
20. The Aquabats Super Show! - Christmas With The Aquabats
21. South Park - Mr. Hankeys Christmas Classics
22. Duck Tales - How Santa Stole Christmas (2018)
23. Home Alone 2
24. Bad Santa
25. Mr. Magoos Christmas Carol
26. Mickeys Christmas Carol
27. The Simpsons - Simpsons Roasting On an Open Fire
28. Olive The Other Reindeer
29. The Grinch (2017)
30. I Want A Dog For Christmas, Charlie Brown
31. G.I. Joe Renegades - Homecoming
32. King of the Hill - T'was The Nut Before Christmas
33. Christmas At Peewees Playhouse
34. The Life and Adventures of Santa Claus
35. Futurama - Xmas Story
36. Jack Frost (The Michael Keaton film)
37. How The Grinch Stole Christmas (2000)
38. Bah Humduck, A Looney Tunes Christmas
39. Looney Tunes Cartoons - Holiday Special
40. Die Hard
41. A Spongebob Christmas
42. Its Christmastime Again, Charlie Brown
43. Its Always Sunny - A Very Sunny Christmas
44. Gremlins
45. Dr. Stone - Spartan Crafts Club
46. Scrooge (A Christmas Carol 1938)
47. Babes In Toyland
48. TMNT 2003 - The Christmas Aliens
49. Jingle All the Way
50. Super Mario Super Show - Merry Cave Christmas