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.

Everything Everything - Photoshop Handsome

Showing my age here, but Michael Caine by Madness.

Ramsey Midwood, Feed my Monkey

Damn near every song by Joshua Ray Walker

Yannis and the Yaw, Clementine

Not massively into D&B but this is one of my favourites:

Keeno (feat. Rou Reynolds) - Shelter From The Storm

Most music I like is considered obscure by my friends...

https://open.spotify.com/track/48Wf7PdYe7oqi55nEFxTJC?si=i_LWRGENTF23CWTHG8CC2A

Anxiety attack by Jeffrey Lewis

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

Come Back to Bed by Valley Lodge

https://youtu.be/z81PWYEQYpU?si=s8pkZcZ9RNL_khGl

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

Not sure if it's obscure since I don't go out much, but "Tastes like Candy" by Kissing Violet and "Wolf" by AlicebanD.

I'm Against the Government - Defiance, Ohio

https://youtu.be/AT0IsmflTxs?si=eAPYyBw20BR-EQ7h

Tythe, Rachel Dradd - The Light https://youtu.be/nx4WcxFdDns

E.O.A. by Bobnoxious

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.

Aydio - Deltitnu

It's super chill.

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.

Native Howl - Thunderhead https://youtu.be/CvBiXBSEGDY?si=qBzVCUfOj1l9BEf6

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.

Little Scandinavian band called Kashmir, mommy in love, daddy in space

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.

Halima Chedli Ensemble - "Touhami Dikr".

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.