First thing that came to mind is a song by a band that I can't even find online. I have the song as an .mp2 file. How's that for obscure?
Here's one that is online: Technical Jelly (Live) - Honor Among Thieves
this post was submitted on 03 Oct 2024
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Not sure if it's obscure since I don't go out much, but "Tastes like Candy" by Kissing Violet and "Wolf" by AlicebanD.
Was not expecting to see anyone else talk about Library Takeout.
I like a lot of obscure songs. Here's one of my random faves: Swamp - Mid-Air Thief
I've always been into freeform radio stations that color outside the lines, college stations like WPRB from Princeton, WFMU from NY/New Jersey, KFJC near the Bay Area, etc., have discovered a ton and a half of stuff that's way off the beaten path and has caught my ear.
Here's a good example I picked up around twenty years ago from KFJC, it could have been any one from too many choices to count, but for some reason this was the first song to pop into my mind right now.
If memory serves, I believe it's a field recording taken in the Sahara Desert, a nomadic people from around Morocco or Tunisia, and can only imagine the magical environment, close my eyes to try and visualize the crisp dry Saharan air at night, a large bonfire, the sky exploding with stars above, and this trance-inducing, mystical chanting.
A song about the infamous East of Adelaide area of London, Ontario which is notoriously run-down compared to the rest of the city. A lot of the things mentioned in the song will sound very familiar to others who have lived in similar trashy neighbourhoods. The song became popular enough in London that one of London's former mayors, Joe Fantana, played the song with the band on the drums.
Anxiety - Optimus Rhyme
Wheelie Cyberman is one of my favorite obscure artists, and both Optimus Rhyme and his current band Supercommuter are great if you're into nerdrap and/or chiptune music (Supercommuter is much more chiptune than Optimus, but there's still a lot of influence there)! A couple more good tracks from both:
Unusual habits - Supercommuter
Bad ideas - Supercommuter
Reel Estate - Optimus Rhyme
Coded and United - Optimus Rhyme
Not massively into D&B but this is one of my favourites:
I like a number of songs by Sid Maudlin. However, some years ago she and her music entirely vanished from the internet. From what little information I could find, she retired and tried to erase that part of her past, along with every single one of her songs.
She was super aggressive with DMCA takedowns and would hit just about anything and everything that mentioned her name or her music. But the internet being what it is, it never truly went away. I think she's either relaxed a bit or given up trying to take everything down.
Ramsey Midwood, Feed my Monkey
Damn near every song by Joshua Ray Walker
Yannis and the Yaw, Clementine
Maybe Tomorrow by Abby Simons:
https://www.youtube.com/watch?v=_WkKi4CbWN0
This is from an old Youtube channel, Abby would write, record, edit, and post a new song every week for a year... almost.
When the song pops into my head from time to time, I miss the way that youtube felt.
CunninLynguists - "The Format" (Feat. Masta Ace & Mr. SOS)
Whatcha Doin to Me by The Reds
https://youtu.be/EqG_PN6Gt3E?si=bfgDl1RkCRnID4ov
I've been listening to it for over 40 years and it still fucking rocks.
No Life King - Black Pyramid is under 40k views so probably that.
My first thought was Cryptkey - Windhand, or some Electric Wizard, but they are definitely more popular in general.
Most music I like is considered obscure by my friends...