A Very Hipster Halloween

What’s up, hipster. Trying to find some good songs to put on your Halloween playlist? Trying to walk the line between ironic old ditties and songs you actually like?

That’s the thing with Halloween. It’s the holiday that walks that perfect line between irony and enthusiasm, make-believe and sincerity. That’s its power. In sharing a collective fantasy through diverse personas that all find some different facet of creepiness, you and your friends get to enjoy an honesty of expression you rarely find throughout the rest of the drab year.

So make sure the punch is ready. Put the finishing touches on your makeup. Get the decorations just so. Don’t worry about the playlist; I’ve got you covered.

1. "Prelude," The Blasting Company

As your friends start to trickle in twenty minutes after you told them to show up, serenade them with this gem from the animated mini-series Over the Garden Wall. Steeped in American Gothic, Wall combines the gorgeous autumn tones of O Brother Where Art Thou with the silliness and hipsteriness of Adventure Time. It’s the perfect show for the month of October.

2. Psycho Killer, Talking Heads

Now that the early birds are finally here, you find that they’re all timidly plastered to the walls with their red cups in their hands. You need to get them moving, and what better way to do that than queue up hipster darlings the Talking Heads? “Psycho Killer,” with its infectious bassline and creepy lyrics, should do the trick. The scariest part of the song? When David Byrne reaches for that high note, ayayayayah!

3. "Ghostbusters Rap," Run DMC

It wouldn’t be a true hipster playlist without an obscurity like this forgotten classic from early hip hop greats Run DMC. Ghostbusters 2 left a bit to be desired compared to its predecessor, but this song from its soundtrack will keep your guests dancing. The sing-songy cadences of 1980s rap pair well with David Byrne’s stuttering delivery of “Psycho Killer.”

4. "Diary of a Madman," Gravediggaz

Keep the Golden Age of Rap going with this classic from horror-rap geniuses Gravediggaz. It boasts one of RZA’s best Pre-Wu Tang beats. Your guests are letting loose, the wallflowers are all in the center of the room, the punch (and the PBR) is flowing, and vibes are good. Creepy good.

5. "Time Warp," Rocky Horror Picture Show Soundtrack

Let’s change the pace a bit to something more upbeat. No Hipster Halloween playlist would be complete without this cult classic hit from 1975 musical Rocky Horror Picture Show. And there's nothing a hipster likes better than to get a reference, so you'll likely see half your guests look up from their drinks with a smile and say, "What, you don't recognize this song?" Maybe you'll even get a few of them to "step to the left..."

6. "People Are Strange," The Doors

Now that they've let loose, take things down a notch with this burner from The Doors. There isn't a hipster out there that doesn't feel a little strange most of the time. The beauty of Halloween is that you're all strange together. There goes a 6 foot vampire bat two-stepping over to the snack bar. In the corner, a goth witch is playing with your cat. A human-sized avocado is chatting up Super Mario. Aren't your friends gloriously weird?

7. "Burn the Witch," Radiohead

"Hipster darlings" is probably not an epithet that Radiohead would embrace, but it's true. And they've always had a kind of Halloween bend when you think about it, with Thom Yorke's creepy non-sequitur images and Jonny Greenwood's ethereal string arrangements. It all comes together in their recent gem "Burn the Witch," which also happens to have a perfect Halloween vibe inspired by perhaps one of the creepiest films ever made, The Wicker Man.

8. "Hurdy Gurdy Man," Donovan.

On paper, this is a beautiful, happy song. A hurdy gurdy is a fun, cool instrument, and the guy playing it is "singing songs of love." There isn't a minor chord anywhere to be found. The rollicking drums and stinging guitar are all, it seems upbeat. What could go wrong?

But somehow Donovan's 1968 hit "Hurdy Gurdy Man" is one of the creepiest songs out there. There's just something about Donovan's low, stuttering delivery, and the way the guitars and drums keep insisting on their steady, unwavering, almost monomaniacal parts. Used to great effect in David Fincher's 2007 film "Zodiac," this song will get those kids back on the dance floor.

And I don't know what the hell a "roly poly man" is but I bet he's scary AF.

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Well, I think you can take it from here my hipster friend. Remember to air on the side of the weird, the obscure, the forgotten, the deep cut, the ironic, and the terribly serious. Remember that what makes hipsterdom glorious is that whatever you do, you do it 100%. So have fun this Halloween, everyone, and stay safe.