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The stories of the 5 most bizarre Christmas songs of all time

Christmas is a time of tradition to such an extent that we even go along with hearing the same old collection of about 15 songs on repeat every year. That’s fine by most people, after all, the Christmas roast is tradition for a very good reason and that can be said for a caveat of other festive familiarities. 

However, some things don’t quite adhere to Christmas quite so well. In fact, some of the outsider artists and other oddities gathered in the collated list below don’t seem to adhere to any conventions or rules whatsoever. Their inherent odious intent is only heightened further by just how much they seem to defy wholesome jingle bells and a hearty ho-ho-ho. 

From mind-bending mayhem that leaves you wondering whether you have unwittingly been lobotomised, to the bizarre ubiquity of an incredibly inappropriate Christmas classic. We’ve waded through the wild west of festive fodder to present to you the most bizarre December songs around.

The five weirdest Christmas songs of all time:

‘Merry Christmas’ by Wesley Willis

Wesley Willis is an outsider musician and artist who found himself embraced by Chicago’s billowing punk rock scene. Therein he became so friendly with the patrons that his signature forehead-based greeting meant that he had a permanent protrusion between his brows. Despite the dark past that he suffered through, this zest for life thereafter made his artistry zip. 

However, it didn’t always zip along on a typical one-track road, there is a lot of contrasting duplicity in the mix. Take, for instance, the chorus for his evangelical anti-cussing songs being an outburst of simply “sh-t and f-ck” six times over. His Xmas epic ‘Merry Christmas’ might not have the same ambiguity about it, but the keyboard jam and mix of rap and wailing choral vocals prove maddening all the same. 

‘Deck My Balls’ by Afroman

Sexual demands, the propagation of gun crime, assimilating the youth into gang culture and, of course, getting high is rattled through in a tra-la-la acapella recital by Afroman and his trusted Christmas brethren. It is not so much the wilful intent to eviscerate the wholesome side of Christmas that proves shocking here, but the fact that they do it in a carol style manner. 

In a musicological sense, this holds all the hallmarks of people knocking on your door to spread some festive cheer and remains positively free of 808s and scratching samples, but in a lyrical sense, it proves less Christmassy than Rudolf being informed of the truth about the dark medical reason for his red nose. 

‘Baby, It’s Cold Outside’ by Betty Garrett and Red Skelton

Speaking of inappropriate Christmas songs, it seems quite amazing that ‘Baby, It’s Cold Outside’ clearly has some enduring charm to it considering it has been played year on year since 1944. It doesn’t take a sociologist to be able to figure out why, but it is clear that the utter madness of the lyrics comes to the fore when the gender roles are reversed, and Betty Garrett pleads with an elder gentleman to stay rather than brace the ravaging cold.

Taken from the film Neptune’s Daughter, the choreography in this particular rendition below is undoubtedly excellent, but everything else about the track needs to be judiciously waded through with a toothcomb about as fine as the Jolly Green Giants hoe. This version has a hint of irony to it that reveals the madness, but it’s remarkable that many others don’t.

‘I’m a Christmas Tree’ by Wild Man Fischer

Wild Man Fischer was a notorious street performer in the West Hollywood area known for his wild acapella verse and ‘”new kinds of song” that rang out down Sunset Strip during his reign. He made enough of a name for himself in this time for Frank Zappa to find him and arrange for him to open for some Christmas show specials for the Mothers of Invention. 

Sadly, it would seem that the festive season since soured for Fischer, because in this 1999 song-poem he takes on the role of Christmas tree and despairingly complains about how he is beleaguered by baubles, watches a fat man commit a home invasion, and then gets chucked out in the New Year. He does this all while Dr Demento repeats exactly what he has but with a half-second delay. 

‘Merry Christmas (Santa Claus, You’re a Lovely Guy)’ by Max Headroom

Some people might recognise Max Headroom from true crime videos owing to the bizarre unsolved TV highjack that occurred in 1987, whereby his laughing head bombarded the radio waves in Chicago in a very apocalyptic fashion. That same terrifying glitching style continues into this Christmas anti-classic. 

Year on year, the dystopian AI hellscape that Headroom seems to represent gets more unnerving, and in this 1986 video, he seemingly prognosticates a very Zoom-based Christmas. The song itself also seems distressingly like the sort of thing that an AI bot would generate if it was forced to listen to an unending Christmas playlist that included all of the above. The only reassuring element is that Headroom sounds not unlike the familiar tones of Jim Carrey. Merry Christmas folks, sleep easy.