The Devil and Mr. Yankovic: the Seven Darkest Songs Ever Written by Weird Al

  • July 25, 2010
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Toothless People


Moving along down the list, Al expands his repertoire to include dissing old people, which is just plain mean unless the old person is one of those freaky octogenarian bodybuilders that can both rip a man to shreds, break their back, and still be done in time for the early-bird special at their local IHOP.

Unlike the other songs we’re tackling today, Toothless People both reads evil and sounds evil, with Al growling over a slithering snake-like beat, heavy on the bass, about how disgusting it is that these ancient fossils have let themselves go to the point where they have no teeth anymore. Admittedly, while getting big ol’ gum-kiss from someone with no teeth is certainly repulsive in its own right (especially if any used denture cream gets on your face during the process), that’s still no reason to condemn them in song. The 90-year-old weightlifters are after you, Al; watch your back.

Quick note: this is the only actual parody on this list, as well as the only song so obscure that nobody on YouTube bothered to make a video about it. Not even a bad one. So you just get to stare at Al in full polka regalia for three minutes. Contain your excitement, and remember to change your shorts afterward.


Good Ol’ Days


Next, we have this, a gentle-sounding James Taylor-esque country ditty about being a total psychopath growing up and how wonderful those memories were. During his formative years, Al goes from mutilating insects during his free time, to arson and attempted murder on a general store owner, all the way to kidnapping his girlfriend and abandoning her in the desert to die of dehydration and starvation. Perhaps this reminds you of your childhood.

The best part of this song is that, after all these years, Al appears to have no idea why he did any of these horrific deeds. He’s basically accepted them as normal stages of youth development, like joining the Cub Scouts or watching in embarrassment as your parents fight each other over your Little League game. Doesn’t everyone burn down buildings and torture young girls before they mature a bit and settle down? Apparently, you haven’t lived until you do.


The Night Santa Went Crazy


Finally, the coup-de-grace, the absolute darkest thing Al ever wrote. For four minutes, Santa Claus decides that he doesn’t like his job anymore and, instead of quitting and taking a menial job at the local Burger King to pay the bills until something better comes along, decides to just kill everybody. Reindeer, elves, police: all of them targets of St. Nick’s rage.

By the time it’s over, Christmas is basically done, as the reindeer are either dead or crazy, Mrs. Claus is obsessed with making money off the carnage, and Santa himself gets carted away to serve at least 700 solitary years in Shawshank. It’s not so bad though, kids; all we have to do is get a fat guy drunk and stick a red suit on him, so we can pretend he’s Santa. We do that at the mall every year anyways.

Detect some horror in another of his Weirdness' songs? Let us know in the comments below!

Written by Jason Iannone – Copyrighted ©

Image Sources

Image sources:

  • - Happy Birthday :
  • - Christmas At Ground Zero :
  • - Weasel Stomping Day:
  • - Melanie :
  • - Toothless People :
  • - Good Ol’ Days:
  • - The Night Santa Went Crazy: