Christmas songs are everywhere at this time of year, and although you can hearthe common ones in every mall, radio station, and other possible outlet, you don’t always get to hear the funny ones.  If you have read my About Me page or my post with my Hallowe’en playlist, you’ll know I love music and I enjoy humour, so this post practically wrote itself.

Although there are lists of funny Christmas songs that exist, I decided to stick only to the ones I found funny and particularly loved.

Why A List of Christmas Songs?

It’s simple.  I can shop for gifts and sort out the food and do everything else I need to do for Christmas, but until I listen to Christmas music, I simply don’t feel Christmasy!

The Playlist To Brighten Your Spirits (Christmas Or Otherwise)

I love many of the secular and spiritual Christmas songs, but for this post, I’m sticking to humourous ones.

Song #1

I’m Dreaming Of A White Christmas by The Drifters.

I know that you’ve heard this song many, many times, but this version is . . . unique!  It’s very enjoyable, though, and if you watch the video (created by Joshua Held) you will have another layer of enjoyment as it is clever, funny, and altogether delightful.

Song #2

Santa Babee by Eartha Kitt

The divine Miss Kitt has that sexy voice that is perfecly compatible with the innuendo of the lyreics.  I never get tired of listening to her or this song.

Song #3

Twelve Days Of Christmas by Bob and Doug McKenzie.  This duo (not really brothers) were part of the Canadian comedy show SCTV and their segment (Great White North) was created in order to fulfil the CBC’s requirement for Canadian content.  This song became an unexpected hit and a pop culture staple.

If you enjoy this song, check out also their advice on having a Great White North Christmas.

Song #4

Ringing Of The Bells by the Muppets

A classic–I really have nothing else to say about this.

Song #5

The Christmas Song by Alvin and the Chipmunks

This is where I confess that to a shameful Christmas secret–I simply don’t feel Christmasy until I hear this song!

A Few Other Posts For You To Enjoy

These posts aren’t full of funny Christmas songs, but maybe they’ll help get you in the spirit anyway.  Certainly those of us who participated in them had a blast doing so.

The Whore School 2025 Christmas Podcast

Mistress Harper, whose podcast Whore School is one you should absolutely be listening to regularly, has done something fun this year.  She’s asked the Mistresses of LDW to submit their versions of Christmas songs that are in the public domain (or a parody of one of these songs).  She’s assured us that it doesn’t matter how badly we sing, which is a good thing as I certainly wouldn’t qualify if perfect vocals were a requirement!  But you can check out her write up about it here

The Happy Hour 2025 December Birthdays Podcast

Although this is not strictly a Christmas or holiday post, definitely check out Miss Kay Marie’s Happy Hour podcast from 16 December 2025 where all the Mistresses whose birthday is in December get together to celebrate their birthdays and just generally have a good time.  Some of us discuss how having a birthday so close to Christmas has an impact on our birthdays, although that isn’t true for all of us.  You can listen to it on Podbean or check it out on Cock Radio!

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Thanks for reading!  Until next time, stay sexy and stay safe.

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