The King of this is Prince
The name is so familiar and you probably only know him by his hits but a deep dive into his catalogue will bring out every emotion in you including sadness.
His 90’s albums are the best for this feeling in my opinion.
(Graffiti Bridge, Love Symbol, Diamonds and Pearls, Come, The Gold Experience - wow, Emancipation, Chaos and Disorder and 80’s Sign ‘O’ the Times, Batman and of course Purple Rain)
(Put that whole album on repeat)
Also not from that era
In fact that ‘grunge’ depressed feeling was all through alternative R&B in the 90’s.
Also notable mention/ explore their discographies because they were inspired by Prince:
This artist -
And this artist -
And this artist -
…
Add:
Luke James
Frank Ocean
Aloe Blacc
Janelle Monae (upbeat reflective music)
Bilal
Erykah Badu
And rappers too -
Outkast
Nas - esp. Lost Tapes 1
The Roots
Common
Black star
Kendrick
Jay Cole
Even some Jay Z
I could go on … but that’s it for now …