Random Rules Playlist 047: Top 40 Unintentionally Creepy Songs Of All Time

Context is everything!

Welcome to a brand new edition of RANDOM RULES! The point of this newsletter is to tell stories via playlists. Sometimes this means providing the perfect soundtrack for different holidays/seasons, or specific times of the day (or weather conditions). So far we’ve also featured DEEP dives into genres like shoegaze, slowcore, outré hip hop and freak folk, playlists for holidays like Halloween, Thanksgiving, Christmas, 4th of July, Pride Month, Memorial Day and Easter, plus fun themed mixes about The Devil, Nocturnal Concerns, UFOs, Insects, diss tracks outside of hip-hop, songs about Florida, plus our ongoing Family Tree series which has covered Talking Heads, Slint, Matmos, Vivian Girls, Pedro The Lion and Pavement so far. You can access the archive, mostly for free, or you can upgrade to paid to have full access to our archive. You can also follow along for more frequent updates on Spotify or Instagram - @djfalkor on both platforms.

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Tiny Tim

Just in time for Halloween, here’s a playlist guaranteed to ruin any party! Personally, I find these songs to be even more unsettling and creepy than anything on my ULTIMATE HALLOWEEN MIX.

The important rule for this playlist is that the artists behind these songs did not write, produce and release these songs with the intention of emotionally scarring us all. In most cases, these songs were brilliantly used by directors / music supervisors in horror movies or TV series to accentuate a particularly haunting / disturbing scene.

Context is everything, and these songs were used in masterful ways, that are burned into the memories of millions (in some cases). Songs like “Bang a Gong” or “Hip To Be Square” I don’t really find to be creepy on their own, but they will now forever be tied in my mind to the films Longlegs and American Psycho, respectively. It becomes impossible to hear these songs without cueing up the corresponding scenes from these films internally.

There’s a few songs I’ve included here that actually AREN’T in any horror films (that I know of). A good example is Johnny Mathis’ “Wonderful! Wonderful!” — I was alerted to this song’s creepiness thanks to Mr. Lou Barlow and the cover version he released on the Sebadoh III album, he really brings a sinister vibe to the song that makes you reevaluate the original.

Here are my picks for the top 40 most unintentionally creepy songs of all time, I’d love to know if you have suggestions for anything I left out:

1.Tiny Tim - Tip Toe Thru’ the Tulips with Me
2.Patience & Prudence - Tonight You Belong To Me
3.Q Lazzarus - Goodbye Horses
4.Luniz - I Got 5 On It
5.Huey Lewis & The News - Hip To Be Square
6.Cass Elliot - Make Your Own Kind Of Music
7.Buddy Holly - Everyday
8.Minnie Riperton - Les Fleurs
9.The Chordettes - Mr. Sandman
10.Evie Sands - Angel Of The Morning
11.Dwight Twilley Band - Looking For The Magic
12.Judy Collins - Both Sides Now
13.T. Rex - Bang a Gong (Get It On)
14.Carpenters - (They Long To Be) Close To You
15.Frankie Valli - The Sun Ain’t Gonna Shine (Anymore)
16.Daniel Johnston - Walking the Cow
17.Johnny Mathis - Wonderful! Wonderful!
18.The Turtles - Happy Together
19.The Ink Spots - We Three (My Echo, My Shadow, And Me)
20.Bobby Vinton - Blue Velvet
21.Ruth Etting - Ten Cents a Dance
22.Stealers Wheel - Stuck In The Middle With You
23.Al Bowlly - Midnight, The Stars and You
24.Santo & Johnny - Sleep Walk
25.Sammy Davis Jr. - The Candy Man
26.Gene Kelly - Singin’ In The Rain
27.Roy Orbison - Crying
28.Stone Poneys - Different Drum
29.Book Of Love - Sunny Day
30.Flanagan & Allen - Run, Rabbit Run!
31.Vera Lynn - We’ll Meet Again
32.Judy Collins - Send in the Clowns
33.Samantha Sang - Emotion
34.Jimmy Durante - Smile
35.The Guess Who - Laughing
36.The Flamingos - I Only Have Eyes for You
37.? & The Mysterians - 96 Tears
38.Donovan - Riki Tiki Tavi
39.David Bowie - Fame
40.Goo Goo Dolls - Iris

Again, please let me know what I missed in the comments!