Your Favorite Holiday Special

I don't see what is odd about it. The 'TV Special' is a type of entertainment product familiar to most westerners who grew up from the 1950s to the end of network tv prominence. These tend to congregate around holidays, with the OP's timeframe limitations approximating what growing up I would have called the Year-end or Christmas-and-Christmas-adjacent holidays. This is a discrete conceptual thing (if hard to capture in a simple phrase), and OP wants to know which ones are our favorites.
It's not the TV Special part. It's the holiday part. Holidays happen throughout the year. If the title said Winter Holiday or something, then it would make more sense.

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Doctor Who: A Christmas Carol.

There are many Christmas specials for Doctor Who, but this is the one I come back to again and again. A reimagining of the Dickens tale that wears its inspiration on its sleeve while making fun and creative use of time travel. Awesome performances and a great soundtrack really deliver the emotion on this one.
This is what I was going to post as well. It's funny and moving in all the best Doctor Who ways.


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3. Seinfeld, "The Strike"
The episode that gave us Festivus for the rest of us! My friends and I actually observe this fake holiday, and "the airing of grievances" has become one of our favorites.

2. Twilight Zone, "Night of the Meek"
The best and wierdest Santa Claus story ever. If you haven't seen it, you really REALLY need to.

1. M*A*S*H, "Death Takes a Holiday"
This is probably the best episode of the whole series. The crew of the 4077th entertain a bunch of local orphans, which adds some much-needed levity to the main plot: BJ, Hoolahan, and Hawkeye work to save the life of a soldier so that his family won't think of Christmas as the day their father died.
I remember that MASH episode! So good.

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