Few examples would be Type O Negatives slower output (Everything Dies, Love You to Death, Pyretta Blaze), Woods of Ypres (album 5), and Katatonia's later output specifically Dead End Kings. Hope those express the kind of gut wrenching and heartache filled themes I am looking for. I guess they all share the commonality that you can sing along to them easily as well.
Beautiful catchy melodies, hooks, and clean vocals would be ideal.
Thanks guys!

Tiamat - Pray, Amanethes & The Scarred People!!

and then the rest:

Paradise Lost - Paradise Lost
Solstafir - Kold, Svartir Sandar, Otta
Saturnus - Paradise Belongs to You, Martyre, Veronika Decides to Die
Anathema - A Fine Day to Exit, A Natural Disaster, We're Here Because We're Here, Weather Systems
Opeth - Damnation
End Of Green - Last Night on Earth, Dead End Dreaming, The Sick's Sense

Just listened to Soltafir's Kold and that is some powerful stuff. Always heard about them and now I see why. Gonna sit with this album for a bit so I don't get overwhelmed with the rest of their discography. Great rec.
Paradise Lost and Opeth I am familiar with their sound, but not those albums.
Tiamat are interesting. Gothic side of Type O cheese turned up!
Gonna spend a lot of time with Anathema as I have seen their name mentioned here numerous times.
Really appreciate the help man, particularly with mentioning not only the bands, but the particular albums as well. Makes digging a lot easier!

no sweat, several bands are like chamaleons, releasing slightly different album per album, so you gotta dig in

Solstafir is a really powerful band, lot of emotion put there, tons of catchy melodies. Whan it comes to album Kold - that's a glorious hymn to the vast winter wasteland and cold blowing winds. You can feel the chill crawling behind your neck!

For Tiamat, I would really go for the last album - Scarred people - it's a milestone deep, catchy but dark, emotive but spitful, and Johan's vocals are just top notch here. You can almost immediately hear floydish guitar layers throught the album, and that Lana del Rey cover at the end is suprisingly good.

Oh and I forgot one more rec:

Green Carnation - A Blessing In Disguise, The Quiet Offspring, The Acoustic Verses

I think you're gonna love it. The prog metal done well, with an tiny touch of melancholy there.

My fav track:
https://www.youtube.com/watch?v=W7GQ0As4SZo

Pink Floyd is one of my favorite bands ever so those instrumental passages and orchestrations are killer for me. Good blend of beautiful melodies while still retaining that darker edge. Gonna start with their latest and work my way back. Thanks again bud and appreciate picking some from different sub genres as well.

Maybe a bit too depressing/introspective, but perhaps Beyond Dawn's Pity Love would be what you're looking for.

It did not hit the spot I am looking for, but I still dug it and it is definitely unique and interesting nonetheless. Good use of trombones!

Opeth - Still Life seems like the perfect album for you. But I also second Damnation.

Other than that
Agalloch - The Mantle
Judas Priest - Sad Wings of Destiny
Dark Tranquility - Fiction
WASP - The Crimson Idol
Sigh - Imaginary Sonicscapes

All these albums are very different from each other (and from Type O Negative) in terms of sound but I think they all share the mood you're looking for.

Funny you mentioned Dark Tranquility's Fiction. I spin that album regularly (nearly every week) as it's an all time favorite for me and highly accessible.
Imaginary Sonicscapes is also my favorite Sigh album

Opeth been mentioned here twice so definitely gonna invest a fair amount of time with their discography. Only really listened to Blackwater Park and the prog stuff.

Ill be giving Agalloch and WASP a spin later. Really appreciate the recs, and youre right I am looking for the mood, not overall similarity in sound.
Thanks!

I strongly recommend Damnation album - it has minimum metal elements, 100% clean singing, etheral sounding and the atmosphere you are looking for Perfect poison for those autumn days.

And to add something more:

Darkseed - Diving Into Darkness
Antimatter - Leaving Eden
Amorphis - Am Universum
Ulver - A Quick Fix Of Melancholy EP
My Dying Bride - 34.788%... Complete
Lake of Tears - Black Brick Road

hope it works

Anything by The 3rd and the Mortal while they were still a metal band should work, but I'd recommend starting with Painting on Glass since you mentioned you like Pink Floyd (and also simply because it's my favourite by them ). It's not that it is super floydy necessarily, but it's more on the experimental / darkly psychedelic side compared to their earlier work while still being mostly metal, unlike what came afterwards.

There are some recommendations I can give you for this, I won't give you a super long list but here are some choice bands/albums to check out:

Bell Witch: Four Phantoms
Aerial Ruin: Ash of your Cares and Nameless Sun
Empyrium: Turn of the Tides and At Night the Wood Grouse Plays
Alcest
Sylvaine
Les Discrets
Fen: Epoch, Winter, Dustwalker etc.
Lantlos: Neon, and Melting Sun

All of these albums evoke so much imagery that reflects these emotions. Enjoy!

My Dying Angel - Angel and the Dark River is my suggestion. What a beautiful album for a hurting heart!!!

The Finns do melancholy well.
(apparently Timo Rautiainen & Trio Niskalaukaus are active again! )

Huge fan of most of those minus the ones I have not heard which are Empyrium and Aerial Ruin. Apparently you understand what I am after Thanks for the help

Lots of My Dying Bride mentions here so looks like it is finally time to take some time with them. Was always fond of their peers and A Forest of Shadows so hopefully this will scratch the itch. Thanks everyone!

Some good ones mentioned already, here's a few I'd either second or recommend myself:

Sylvaine - Wistful
Bell Witch - Mirror Reaper
Doom:VS - Earthless
SubRosa - More Constant than the Gods
Draconian - The Burning Halo or Sovran
The Old Dead Tree - The Nameless Disease
Red Moon Architect - Return of the Black Butterflies

Judging from your comments you already know the first two, hopefully some of the others take your fancy too.

What is everyone's thoughts on Sylvaine, she is one of those up and comers in the Alcest tree of black shoegaze. I was just listening to "Delusions" on my way into work today. The stuff is fantastic I think, looks like she is also working on a new album soon. If any of you got a chance to hear Aerial Ruin let me know what you think!

Cheers!

I imagine it's highly likely you've heard Sentenced, but on the off chance you haven't, give these songs a go:

No One's There
The Rain Comes Falling Down
Drown Together
Killing Me Killing You
End of the Road

In The Silence - A Fair Dream Gone Mad
( https://www.youtube.com/watch?v=Kg2AhACpi3o )

Yeah that was a spot on rec. Thanks for giving a newer band too, will keep an eye out for their second album.

Surprisingly never heard of these guys, but like the last this was also a great rec and lots to dig into.
Making my life easier, thanks guys.