1. Halloween, by The Misfits
Can't do Halloween right without this classic from horror punk legends The Misfits. This song pretty much encompasses everything that makes the night so creepy, scary, special and just downright awesome. The whole thing just sounds evil in all the best ways, especially the creepy sounding vocal harmonies in the chorus that just moan "Halloween" over and over again. Never heard anything like it before in my life and I couldn't be happier.
2. Sweet Transvestite (Rocky Horror Picture Show), by Richard O'Brien
Halloween also isn't complete without going to the Rocky Horror Picture Show! This in my opinion is one of the most iconic songs on the whole soundtrack. It's a lot of fun to dance and sing along to and quite frankly it's just silly, especially in the context of the movie. You don't really take it seriously, but at the same time you can't help but finding yourself singing it long after it's over and you're around people who probably would think you weird singing a song originally sung by a man in pearls and heels.
3. Killer, by Alice Cooper
I think this song is one of the original Alice Cooper band's greatest masterpieces. It has this sense of overall dread the entirety of the time it's going, but with the way the end turns into a dirge with the condemned man being killed and then his soul entering Hell it definitely gives goosebumps. It's no surprise that this is the song that has been used at Alice's concerts for the past few decades for when at the end of the show Alice gets executed (usually by beheading).
4. Thriller, by Michael Jackson
I know, I know. Michael Jackson doesn't usually fit the mold of this blog, but f*** it. It's Halloween! Can't go wrong with attempting to do the iconic dance to this catchy upbeat funk tune. Plus, anything that horror icon Vincent Price is involved with is virtually guaranteed to be gold. You might not like the man for what he may or may not have done in life, but you've got to admit that he really knew how to write a song and dance.
5. Walpurgis, by Black Sabbath
This demo is the original version of the Black Sabbath classic War Pigs. This version has a lot darker lyrics with themes of witchcraft, Satan, burning churches and priests, etc. Their record label was not too fond of these lyrics and forced the band to write a whole new set, lest the whole song be dropped from the album altogether. I can kind of understand why they did that. People in 1970 were NOT ready for this kind of thing. Listening back though, it's kind of fascinating to hear the origins of this Sabbath staple.