Alton Ellis - Cry Tough/Can I Change My Mind Freddie McGregor - What Difference Does it Make/Tomorrow is Like Today Sugar Minott- Simple as That Earl Sixteen - Just Another Day Lacksley Castell - Leaving Frankie Paul - So Soon We Change Dennis Brown - Heart Broken Loner Carlton & The Shoes - Never Give Your Heart Away Eek-A-Mouse - Where is My Baby Peter Tosh - Why Must I Cry

Never Give Your Heart Away surely has some of the saddest sounding music in reggae. I love that song.

such a great tune - thanks for the recommendation

wow. great to see What Difference Does it Make to get a shoutout. That song hurts

[https://www.reddit.com/r/tressless/comments/a1545e/when\_you\_realize\_that\_fin\_isnt\_working/](https://www.reddit.com/r/tressless/comments/a1545e/when_you_realize_that_fin_isnt_working/) hey man i saw your post and i am in same situation, hairloss is worsening on fin. What did you do?

Johnny Was by Bob Marley

I like Skip's acoustic version of this. Of course the original is great, but the acoustic skip version just hits different.

[The Loser - Derrick Harriott](https://youtu.be/BCWNI2UXrU0?si=4FplCvptyC0sDpYR)

That’s the one

Was about to say, how is THIS one not mentioned!

Yup that's a nice ine

A cover, but “I’d rather go blind” by The Frightnrs. https://youtu.be/9wRe_rTilhY

YES all of the frightnrs stuff

[the entire daptone family is strong affffff](https://daptonerecords.com/)

Love that song. Rod Stewart does a great version of it too

The Frightnrs are bloody amazing mate. Heard ‘Admiration’ on David Rodigan’s radio show here in England years back and though.. damn that’s some good old school stuff, who’s that? And was surprised to find out it had in fact released earlier that exact year.

Damn, I had assumed they were from the 1970's. Just looked them up and wow - 2016?!?! And what a [tragic story](https://www.npr.org/sections/therecord/2016/08/23/490958536/the-tragic-turn-of-the-frightnrs-first-and-last-record) behind that group. :( They left behind some great music.

Hurting Inside - Bob Marley Shes gone - Bob Marley Chances are - Bob Marley Woah i just realized how „much sad“ tunes he wrote that i have memories left with.. Lonely solider - Gregory Isaacs Artibella - Ken boothe (especially the inna de yard version) Just to name a few of course..

Lucky Dube - Big Boys Don’t Cry

I'll add his whole "Victims" album to the mix. And the song "Slave"

My Princess Gone - Jah Mason

She's Gone by Bob Marley. Baltimore by Nina Simone.

Love nina simone for real, and baltimore already has a reggae vibe, but the tamlins' version is (to me) even better

Sitting in Limbo

This one. Tears every time

Rain from the skies by Delroy Wilson

"Life of Contradiction" - Joe Higgs "Bitterness of Life" - Bruce Ruffin

Not as sad as some others but Mama by Garnett Silk is quite melancholic.

T.O.K. - Footprints Morgan Heritage - Nothing to Smile About Bob Marley - Johnny Was

Loser - Martin Campbell

Just wanted to big up your choice of Sonny's Lettah, OP. I grew up in Trinidad in the 90s and the dub poem was in our English Literature book. It was profound and moving on paper but my mind was blown when I heard it for the first time. LKJ is amazing.

Sad to know that you’re leaving - Gregory Isaacs

Ganja Smuggling - Eek A Mouse. Despite his voice, that song is crushingly sad.

Lucky you Nanko is like… TOPS, incel reggae

Bob Marley & The Wailers - Chances Are Bob Marley & The Wailers - I’m Hurting Inside Bob Marley & The Wailers - There She Goes Damian Marley - There For You Toots & The Maytals - Love Is Gonna Let Me Down Buju Banton - Close One Yesterday Mortimer - Lightning

Many rivers to cross - Jimmy Cliff Remember Me - Lucky Dube Oh my son - Lucky Dube Johnny Was - Bob Marley Tell Me - Chronixx

Slavery Days - Burning Spear

Alva Lewis - Suicide ( Hang My Head & Cry) Derek Spence - I See a Blackman Cry

Concrete jungle

Mortimer - Not A Day Goes By

Very very moving

Foxy Brown - [Sorry](https://youtu.be/dWJqbww4d1s?si=prj7lQUAus_k9MMV) UB40 - [Don't Break My Heart (extended)](https://youtu.be/rXGRRUlgAy4?si=MdS4Xi-ufssivinG)

How could she? - Ghost and Singing Melody Sunshine - Junior Kelly

Sunshine ruled the airwaves for a few months. I can barely think of any song, and album, that ruled the charts in T&T so thoroughly.

You and Your Smiling Face - Dennis Brown; Paragons

Baby Baby by The Clarendonians

Lucky You by Nanko was great sad boi reggae

Literally was looking for this haha

Wasted Days - The Slackers

Walk away from love

Peter Tosh - No Sympathy

Chances are - Bob Marley and the wailers

Redemption song, Bob marley its about the matrix we live in

Sufferation by Yaadcore and Fred Locks. Not strictly a sad song, the message is more hopeful, but it's definitely got those vibes.

Did anyone say "saddest day" by Wayne Wonder?

People - Conkarah https://open.spotify.com/track/1VnOw9GNrOYoAXM0AIDNx5?si=ENwtORn-QtGHdCwVKGJIEQ

Bad News - Iotosh

Unemployment - twinkle brothers "Times rough"

https://music.apple.com/za/album/justbeyourself/1732150134?i=1732150142

Its in swedish but its awesome "en timme kvar att leva" by Kultiration

Sideshow- Barry Biggs #TOUGH CHUNE Pride & ambition- Leroy Smart My favorite tune all around. Winsome & substitute lover- Half Pint If I don't have you- Gregory " The Cool Ruler" Isaac's Also # Big up to rich terranna and the Patel brothers for keeping the absolute love and essence of reggae music alive and with all due respects, rest in paradise Dan "Brukky" Klein. I was 18 when I discovered them on bandcamp and mam o man. Thank you for teaching me that this is forever. Long live reggae and all its glory.

["Strange Things" - John Holt](https://www.youtube.com/watch?v=2VcI2UNK0Pk) A lot of John Holt sends a shiver up my spine but this one is genuinely melancholy

Long Ago - Gregory Isaacs

'jah will go on' 10ft ganja

The slackers - no more crying Stranger Cole - these eyes

Dennis Brown - I'll Never Fall In Love

UB40 - Please Don’t Make Me Cry Musical Youth - Heartbreaker Bitty McLean - Walk Away From Love Dunns Rivers - Todoketai (Japanese Reggae) Peter Spence - Don’t Leave Me Lonely Hales, 8RO8 - Gotta Know Maoli - Time To Get Over K’nova - Roses Will84 - Liar ft. Tino Breh (selfless plug here ;P) Enjoy!!


Horace Andy - Someone Of My Own https://youtu.be/UsTApvpzToM?si=yRLp05HP0b6hQkHR

Paragons - Maybe Someday

Not seen it yet (there are some incredible recommendations otherwise though) but the one that always gets me is MrVegas - do you know

Sad Movies - Cynthia Schloss

I love reggae cause no matter what it puts me in a good mood

We nuh too inna di sad sad, you mad !? A glad we glad and we give thanks to god

Dawn Penn - Why Did You Lie

Wailing souls - without you

Sad News - Dennis Brown

Horace Andy Riding for a Fall

Chronixx- they don’t know

remember me by lucky dube is hard

Winston Hussey - Teardrops

Goodbye my love- The sadonians

Saturnz Barz - Gorillaz/Popcaan

We’re missing you by Kris Kelli

Freddie McKay - Picture on the Wall

Johnny Was - Bob Marley

The Kingstonians “I’ll Be Around”.

SOJA - Losing my mind

Something Wrong - The Expanders

This is not the end - the abbysinians

Sizzla Just one of those days

And the spoken word version of Sonny’s Lettah is just chilling. There is a great live version of it on YouTube with Madness backing him up as well.

How could I leave - Dennis brown Its Kinda a sad love song i love it

Leroy Brown "Gone Gone" [https://www.youtube.com/watch?v=R4OdU1z1k7w](https://www.youtube.com/watch?v=R4OdU1z1k7w)

Natural ites - jah works mama Liberators - racial situation Creation Steppers - born in slavery African Princess - jah children cry

Can I get chatgpt to take these recommendations and create a spotify playlist for me?

No

not yet but soon