OK, so here’s something completely crass, but it fits the “fun” element of the playlist: a song found on a number of Bob & Tom Show collections, where the song originated.
There’s no video for this song (a common trait among holiday songs), but I’ve found a YouTube video that fits the camp of this song which purports to be posted by one of the song’s writers (I believe it). But unlike many of the novelty Christmas songs, there’s not weird singing or a gimmick (“ALLLLLVINNNNNN”) to carry the song, but instead a pretty talented singer, singing over a very Christmas-y and orchestrated tune. It manages to find a solid number of ways to rhyme words that are synonyms for boobs, so it’s got that going for it.
I don’t have any other Christmas songs that fall in this category right now (share in the comments if you do!), but there’s a devilishly dirty song by Peaches that goes the same way. OK, there’s a lot of devilishly dirty songs by Peaches, but this one manages to be dirty and yet “Tent in Your Pants” is one of the tamest songs she’s released to date. Random connection: the song was co-written and co-produced by Greg Kurstin, who also happens to be one-half of The Bird and the Bee.