[Listicle] 15 Vintage Halloween Songs To Get in the Spirit
Get ready to howl along to these vintage Halloween songs
You know how there are some people that listen to Christmas music all year long? I mean, I don’t agree but I understand the logic. On the other side of the coin, I listen to Halloween music all year long. But there are only so many times that you can listen to “Monster Mash” before you want to touch one of Frankenstein’s monster’s electricity bolts. Don’t fret, dear and spooky readers because this creepy lady has your back. The early to mid 20th century was filled to the brim with Halloween novelty music and spooky-themed songs from blues to instrumental to do-wop and more. If you need some good Halloween music suggestions, then look no further than this fun and comprehensive list of vintage Halloween songs which are all available on YouTube! Let’s get listening (and maybe a little spooky dancing) in no particular order.

Bogey Wail – Jack Hylton (1929)

Prepare to have the chorus stuck in your head for a while. I love this one because it’s just so damn catchy. This song, recorded in 1929, talks about the feeling and chills you get when you hear the disembodied wailing of a ghost. This is one of my favorites because of the melody. The music slides up and down to imitate the wailing of the bogey.

Headless Horseman – Kay Starr (1934)

It’s safe to assume that most of us are fans of The Legend of Sleepy Hollow and we are familiar with the Bing Crosby version of this song BUT did you know that Kay Starr tackled the Headless Horseman? I bet you didn’t and now you do. This is just a really fun version and Kay has a lovely voice. This version is a bit more kicky than the original and a lot of fun to sing.

The Wobblin’ Goblin – Rosemary Clooney

If you ever had to drive a car that was on its last leg and would drop a new and possibly important part every time you drove it, then you will appreciate this song. This song is about a poor goblin who’s broom is wrecked all to shit and the only time he gets to fly is when he hitches a ride with whatever witch will let him tag along and literally ride piggyback style. Don’t worry, though, because he ditched the broom and got himself a private jet. Little goblin is living large and in charge now.

With Her Head Tucked Underneath Her Arm – Cyril Smith (1934)

This is a fun little ditty about royal decapitation as Cyril Smith sings of Anne Boleyn and her inevitable beheading by Henry VIII. Don’t worry, he didn’t get off easy because now her ghost roams the castle and bitches at him for cutting off her head. She carries her head tucked under her arm (very inconvenient for when she sneezes) and haunts the castle forevermore. I don’t condone the beheading but I do love a story where a man gets nagged for the rest of his life until he literally dies. Karma, baby.

T’aint No Sin – Dan Russo (1929)

With global warming a very real issue and summers getting hotter, it seems almost impossible to escape the heat. No worries, because Dan Russo has you covered. When not even frozen treats will help the excessive sweating, strip that skin off and dance in your bones. I mean, you can’t sweat if you don’t have sweat glands anymore. This is a really creepy yet VERY danceable song about dancing around in your bare bones.

Skeleton in the Closet – Louis Armstrong (1936)

Louis Armstrong is a treasure and a musical legend. You may know him for his sweet and uplifting songs or even his Christmas song, but did you know he did spooky Halloween music too? This song isn’t his only foray into Halloween music but it is certainly one of my favorites. “Skeleton in the Closet” is about a big group of monsters getting together and having a huge party full of dancing and merriment so fun that even the skeletons in the closets started dancing and rattling his bones. There are all of the classic monsters in attendance and this is sung the famous Armstrong way.

The Night Before Halloween – Bill Buchanan (1962)

The 60’s almost literally oozes from this song and I love it. “The Night Before Christmas” is SO passé because we have “The Night before Halloween.” Prep your Devil’s Night with this tale involving monsters sung in a classic, “Monster Mash” fashion. This song was a DJ favorite and fun to listen to on October 30th. It may even make you twist.

The Headless Horseman – Bing Crosby (1949)

Now, THIS is a classic. I have been a huge fan of the Disney animated version of The Legend of Sleepy Hollow since I was a child and Bing’s buttery voice makes this song just perfect. I am not sure what else to honestly say about this song. Perfection!

The Ghost of Smokey Joe – Cab Calloway (1939)

I LOVE Cab Calloway. This song is fun to sing along to with its “hi-de-hi-de-hi’s” and “ho-de-ho-de-ho’s”. The singer is the ghost of Smokey Joe and his voice is phenomenal and the instrumental bits are smooth and silky. Cab Calloway is best known for his wicked scatting and this song gives you just a little taste. Cab Calloway had a huge stage personality and he was the first African-American musical artist to sell a million copies of a record just because of one song, “Minnie the Moocher.”

Haunted House – Ray Noble and His All Star American Orchestra (1931)

This is definitely a favorite of mine. This song is so damn jazzy and I love the little skit in the very beginning. You can’t listen to this song and not feel like dancing. I also can’t stop myself from singing the song in all of the voices, much to the dismay of those around me. The tempo change is a lot of fun and I hope you love it as much as I do.

I Was a Teenage Monster – The Keytones (1961)

Maybe big band Halloween isn’t your jam and I totally get that but fret not because there are vintage Halloween songs from later decades too. You want the ’60s? You got the ’60s! Because this song came out in 1961, this still has a bouncing ’50s style that would change to more doo-wop into the ’60s. You can almost imagine yourself dancing on a beach wearing a little bikini and a werewolf mask…just me? Okay.

The Monster’s Hop – Bert Convy (1958)

This 1950’s ditty is closer to feeling like the “Monster Mash” in its style but isn’t as played out. I won’t pretend that Bert Convy sings well in this because he doesn’t but his talking-style singing actually works with this song. The repetitive baseline is addictive and you will start bouncing before you realize it. Plus the song is about a bunch of monsters having a wicked dance party. 

The House is Haunted – Roy Fox (1934)

While this may not TECHNICALLY be a vintage Halloween novelty song, it is definitely one of my favorites to play this time of year. The man singing may not be haunted by a ghost, but he’s haunted by the love that he lost and she left her echoes everywhere. The melody is sweeping and, for lack of a better term, haunting. The orchestral parts are just as sweeping as the vocals. If you like more Gothic-style romance-driven spooks, this one is a win.

Trick or Treat – Paul Smith and his Orchestra (1952)

If you have ever watched Disney’s Halloween Treat, then this song should be very familiar to you. As a kid, I watched the VHS tape on repeat and this song was one I sang on a regular basis. It is VERY Disney and the style makes me think of old Disney movies like Peter Pan. I love the blatant Halloween themes and it brings back really good memories.

Nightmare – Artie Shaw (1938)

Not everyone is going to like this one but if you appreciate instrumental music, I think you will enjoy it. The intro is low but then the horns come in a smack you in the face before a clarinet comes and lulls you with its buttery sounds. Artie Shaw was one hell of a clarinetist and this song is so smooth. With the low, humming base it reminds you that this song is indeed about a nightmare and Shaw is just drawing you into the dream world.

If you are looking for something a little bit more apocalyptic than spooky, I would suggest Folk Songs for the 21st Century by Sheldon Allman. If you have played Fallout 4, then you are familiar with his work, which is included in this album. Songs like “Crawl Out Through the Fallout” and “Radioactive Mama” really put you in an apocalyptic and sci-fi mood. If you are having a Fallout themed night, this is the perfect album for you.

I hope you liked these vintage Halloween songs and I hope everyone has a fun, safe, and socially-distanced Halloween! Stay spooky! And, if we somehow missed some vintage Halloween songs that you think should be on this list, let us know!

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