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Old Timey Halloween

A Halloween Playlist for Classy People

By Micah DelhauerPublished 2 years ago 9 min read
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You stand in the corner, red solo cup in hand. On one side of the crowded room is Chris in his typical, phoned-in costume: this year a phallic baseball cap and a name badge that reads “Dickhead.” On the other side of the room, Eddie stands awkwardly, having outdone himself with his Lorde of Darkness costume, a masterpiece of prosthetics and layered armor that seems to have rendered him incapable of moving. Perusing the females in attendance, you think you’ve seen every “sexy” costume there is until Debra walks in dressed as a cleavagy avocado.

On the radio, “I Want Candy” fades to what must be the fifth playing of “Thriller.” Several drunken nostalgics rush the middle of the room to butcher the iconic dance. Maybe next year, you think, I’ll try something different.

And something different is what you’re about to get. Let the commoners slosh themselves with Natural Light while dancing “The Time Warp” for the umpteenth time. You’re looking for something more refined, more old-world: grim but elegant, underscored by the clinking of champagne glasses and the crackling of an antique record player.

Whether you’re throwing a Jazz-era Halloween bash or hosting a period murder mystery party, here’s a tracklist of vintage tunes to invoke the spirits of decades long deceased.

1900s

More Work for the Undertaker - Dan W. Quinn (1902)

The oldest song on the list, this novelty ditty with tinkling piano takes grim delight in describing the demises of various unfortunates, concluding each verse with a head-shaking pun (such as when the parents of a mangled football player receive their son’s remains and learn they only got “a quarter back.”) Dan W. Quinn was one of the earliest recording artists, and while the sound quality on this ancient 78 isn’t the greatest, it’s a funny little tune with a devilish sense of humor.

1910s

At the Devil’s Ball - Maurice Burkhart (1913)

A man dreams that he attends a party in the underworld where he meets, among others, the Devil’s wife and his own mother-in-law. This cute vaudeville number has a wholesomeness one wouldn’t expect for a party in Hell.

Suicide Blues - Arthur Collins (1919)

The singer of this Ragtime lament describes the various ways he’s going to off himself, including bathing in acid, drinking gasoline, and hanging himself from a weeping willow tree (the definition of overkill). It’s like Ragtime and Goth had a beautiful baby.

1920s

Dead Man Blues - Jelly Roll Morton and The Red Hot Peppers (1926)

Jelly Roll Morton was an early jazz influencer who claimed to have created the genre himself. In this orchestral number, he and his band evoke images of a New Orleans jazz funeral, melancholic while at the same time whimsical, setting a tone that is both grim and fun.

Bogey Wail - Jack Hylton (1929)

This bouncing jazz tune recounts the words of an old graveyard caretaker as he describes the haunting noises he hears at night. Cartoonishly spooky, “Bogey Wail” is pure Old Timey Halloween.

Dancing the Devil Away - Vaughn De Leath (1920s)

The now-forgotten crooner Vaughn De Leath was a radio sensation in the 1920s, and this fun dance hall number describes the compulsion to move your feet when the devil “gets into your shoes.”

The House is Haunted – Glen Gray and the Casa Loma Orchestra (1929)

The ceiling is white but the shadows are black / A ghost in my heart says she’ll never come back.” The song paints a lyrical portrait of a sad old swinger alone in an empty house after his lover has left him.

Devil’s Gonna Git You - Bessie Smith (1928)

The Empress of Blues warns her two-timing man that he’s bound for perdition. Her words are unforgiving, but the melody is so darn catchy.

Haunted Nights - Duke Ellington and His Orchestra (1929)

An instrumental piece for jazz orchestra, this short song plays at a sepulchral pace that brings just the right amount of gloom to a vintage party.

Graveyard Dream Blues – Ida Cox / Bessie Smooth (1923)

A woman recounts a dream in which she begs the gravedigger to return her dead lover to her. This wailing blues number with tinkling piano was originally recorded by Ida Cox, while Bessie Smith followed with her own version three months later.

Taint No Sin - Dan Russo (1929)

This 1920s pop number submits the odd proposition that, when it gets too hot, you simply “take off your skin and dance around in your bones.” Imagine a group of giddy skeletons doing the Charleston and you have an idea of what this song’s all about.

1930s

The Ghost of Smokey Joe - Cab Calloway (1939)

Calloway wrote a series of big band jazz numbers following the misadventures of hoochie coochie dancer Minnie the Moocher and her enabler boyfriend Smokey Joe. This song concludes their story with Minnie having kicked her drug habit while Smoky Joe has kicked the bucket.

Mysterious Mose - The White Star Syncopators (1930)

This jazzy selection about a mysterious whistling figure was originally recorded by Ted Weems and His Orchestra, though The White Star Syncopators version released the same year is arguably the more famous. It was also featured in a Betty Boop cartoon of the same name, and perfectly embodies the bouncy oddness of those unnerving black and white Max Fleischer cartoons.

Haunted House - Memphis Minnie (1937)

Plunking piano keys underscore this account of a woman whose house is haunted by the spirit of her late husband. If there were ever a reason to sing the blues, this would be it.

The Boogie Man - Todd Rollins and His Orchestra (1934)

The titular specter taps his toes to the syncopated beat while threatening to frighten “bad little girls like you.” Not a nice fellow, but just try not to hum along.

Nightmare - Artie Shaw & His Orchestra (1936)

Written a day before it was first performed, this jazzy dirge was crafted by Artie Shaw as the signature number for his band. Short and wordless, it sends out funereal vibes, haunting and somber without ever becoming a drag.

Skeleton in the Closet - Louis Armstrong with Jimmy Dorsey and His Orchestra (1936)

“Boy, don’t you go in there!” cries the legendary Armstrong, sounding just like the kind of crotchety oldster who’d tell you off for playing near a haunted house. Then the band starts up, providing a raucous accompaniment for a party of witches, goblins, and all manner of ghoulish creatures.

With Her Head Tucked Underneath Her Arm - Rudy Vallee & His Connecticut Yankees (1937)

This darkly comedic English ballad narrates the ghostly Anne Bolin’s search for revenge against her husband, Henry VIII, who sentenced her to be beheaded. Originally recorded by Stanley Holloway, a cleaner-sounding version was produced by Rudy Vallee in 1937, and it is this version that is recommended.

The Devil with the Devil - Larry Clinton Orchestra (1938)

So what if Satan’s a-waitin’? Having fun is what it’s all about, consequences be damned. So declares Larry Clinton in this big band number, ignoring the voices of reason as he sings and dances and does whatever else has him bound for the pit.

The Haunted House - The New Mayfair Dance Orchestra (1931)

When the doors all squeak and the windows creak and the ceilings leak and the roof’s antique if you hear a shriek and your legs feel weak—it’s the Haunted House!” This comedic foxtrot is a vintage Halloween classic with fast, clever lyrics and a frenetic rhythm bound to get you dancing.

1940s

Gloomy Sunday - Billie Holiday (1941)

Also known as “The Hungarian Suicide Song,” this lament comes right from the heart of a lover who chooses to end their life to be with their beloved in Heaven. Holiday’s version of the song was banned by the BBC until 2002, and urban myth links the haunting number to countless suicides. Many versions of this song exist, with the original English version being recorded by Paul Whiteman & Johnny Hauser in 1936. Later versions added a copout “it was all a dream” ending.

The Boogie Woogie Man - The Brian Sisters (1942)

This pint-sized number recalls “Boogie Woogie Bugle Boy of Company B” by the Andrews sisters, though with the ghoulish themes appropriate to appear on this list. This song was performed as part of a musical short film, the frightened sisters huddling together while a band plays behind them.

Boogie Woogie Man - Glen Gray (1942)

The “Boogie Man” pun was apparently a popular one. Unrelated to the Brian Sisters song of the same name, the Boogie Woogie Man in this selection plays nightmare-inducing music while you sleep at night.

Mommy Please Stay Home with Me - Eddy Arnold and His Tennessee Plowboys (1945)

Taking a break from all the jazzy fun, we have this country/folk song which forsakes the bopping skeletons and instead tells the tale of a little boy who, portending an ill fate, begs his mother not to go out drinking. When she returns home, the previously healthy child dies of some unnamed illness. Let that be a lesson to all mothers who just want one night out of the house.

Don’t Make Me Go to Bed and I’ll Be Good - Roy Acuff and His Smoky Mountain Boys (1946)

Another folk number, this might be the most disturbing song on the list, one that seems to predict the terrors of the Nightmare on Elm Street movies. A playful child is told to go to bed by his father, and becomes seized by terror at the prospect. The child later dies in his sleep, weeping, “Don’t make me go to bed and I’ll be good.” The song is so melodramatically morbid it becomes funny—or is that just me?

Murder at Peyton Hall - Charlie Barnet and His Orchestra (1941)

Starting with a scream, the song launches into a frantic rhythm that suggests the frenzy of horrified murder witnesses and the wailing of police sirens. It doesn’t need any words to create a feverish atmosphere perfect for a graveyard dance.

The Headless Horseman - Bing Crosby (1949)

Finishing off, we have the signature song from Disney’s The Adventures of Ichabod and Mr. Toad. The tune has been recorded numerous times, though the version recorded for the studio album “Ichabod – The Legend of Sleepy Hollow” has become an enduring classic.

Full Playlist: https://youtube.com/playlist?list=PLzwE4RzGkFDtuz8GGPKRxDrwOjowklTBl

playlist
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About the Creator

Micah Delhauer

Writer. Filmmaker. Alectryomancer.

I specialize in stories of the macabre and the amazing, the weird and the wonderful.

Please, read one of my stories. Or find me at micahdelhauer.com, FB or IG. Or just wait around. I'll show up eventually...

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