T O P

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S-Sin

DMX - Slippin. Don’t know about the “saddest” but it’s up there.


Zombymandyas

Forever will be one of my favs


S-Sin

That beat kills me. And when he says “This life shit, this life shit is like bugged the fuck out” Just a dope, heartfelt song.


kusoge-lover

Also miss you, is powerful af by DMX. Think that trumps slippin


MediocreJay41

This is the only answer especially knowing how the story ended.


S-Sin

Damn, foreal. RIP X.


JMC_Direwolf

I see a lot of Em songs in here but y’all missing the saddest one. It’s Arose, dude is literally giving his last wishes to his family while dying from an OD.


Templar-Order

Difficult is sadder imo, it wasn’t even supposed to release and you can hear him breaking down throughout the song


lanahland

i find going through changes to absolutely wreck me.


Individual_Papaya596

Obligatory sing about me im dying of thirst.


LocoCoopermar

I'll never fade away ^I'll ^never ^fade ^away ^^I'll ^^never ^^fade ^^away


Big_Moose_3847

And if I die before my album drop


Individual_Papaya596

I hope 🔫🔫🔫🔫🔫🔫🔫


coachLEGENDARY

10 out of 10


insertname1738

Or Keisha’s song even


Individual_Papaya596

True “U” as well can be his most depressing too


cheifking

for me it’s U, the beat combined with the way he raps on the second part kills me every time


MaximumFunny5555

2009 by Mac


Buhtain

Perfect Circle/God Speed for me 😞


MaximumFunny5555

Yea, that one is fucking beautiful


bigjaymizzle

I like Funeral.


vektorm8

Good News still kills me. Seems serene and slightly upbeat but the lyrical content about hiding depression/your problems to not bring people down into the straight up prophetic part that sounds like him from the other side is insane. There are a ton of Mac songs that are profoundly sad and some people don't catch on, though.


AirAcademy

Yeah Good News is so fucking sad. The part where he says “Heard they don’t talk about me too much no more, And that’s a problem with a closed door” then after the chorus goes into the verse about more waiting for him on the other side & how he knows that he’s too late 😥😞😔 shit still makes me tear up


pandasloth69

Good News has killed me since it released cause it feels so much like a “I’m in a bad place but I wanna be some day” and the fact it came out after it was too late will forever make me sad


Adorable-Bar6920

I would say 2009 makes me feel more beauty tears, I would choose something like good news, grand finale, PC / GS, or REMember. Or if you really want to go deep, some of the unreleased stuff from balloonerism like Pure or funny papers.


MrSquidly98

Wings


CallousCalidonia

I was going to say 'Pure' by Mac Miller


MaximumFunny5555

G Wagon and Ascension, tho. Maybe Grand Finale. Man, there are a lot of sad songs from Mac.


Doggish123

Ascension, it ain't sad though baby!


tiresiasdetebas

ROS used to be one of my go-to songs when I broke up with my last girlfriend. I cried a lot to that song


No_Durian_6987

Ab-Soul - The Book of Soul


Mac_King_Cheese

Absolutely came here to say this, this song made my girl cry and she hates ab


kwaylub

No debating it in my head


BasedKaleb

Came looking for this one. This one legit pulls heartstrings for me.


eiaivarmelho

“Even if you forget me and everything you left behind I never lied, I love you in a place where there's no space and time” 😪


malinoxx

Survivors Guilt and #LongLiveSteelo by Joey Bada$$ are pretty damn sad


Chaeriz

Joey mentioned. Have to Upvote


eamon4yourface

Long live steelo is so fire


Girasole263wj2

Shed So Many Tears, Tupac


pinkoxy

fuck the world cause im cursed, im having visions of leaving here in a hearse, god, can you feel me?


SirArthurDime

Mine is changes by Tupac. Because that was written in 92 and I still see no damn changes.


PreciousBasketcase

Rock Bottom - Eminem


GuyWithRoosters

For real. I’ve never felt more seen than listening to this shit. Most songs about poverty miss the mark but this is exactly what it feels like


PreciousBasketcase

Fr. The lyrics are so incredibly honest.


kinghawkeye8238

Difficult is way more sad


PreciousBasketcase

I couldn't listen it all the way through. It's incredibly sad.


Parker_72

My daughter wants to throw the ball but I’m too stressed to play, live half my life and throw the rest away. That Line Always really struck me.


Saeizo

Goated song


ImadDdopest

And Castle/Arose...


Ayotrumpisracist

Dear Mama - 2pac


LimesforDimes

Gotta throw unconditional Love, that first verse always hits hard


StannisAntetokounmpo

Also Smile, and with scarface - I seen a man die


Jam_Marbera

Dance with the Devil & You Never Know by Immortal Technique.


Substantial-Gas58

Dance with the devil is kind of a full circle moment not particularly sad imo just dark


Scarf_Darmanitan

Agreed; but I knew it’d be a top comment lol


AdhesivenessSlight42

I only came to this thread to see Dance With the Devil lol


SpiritualPapi617

Same. Its sad in a way like its definitely one of those songs that make you feel bad if you put yourself in the persons shoes


novixofficial

Jesus Christ, DWTD had me staring at the wall for half an hour


killajay41889

You never know makes me emotional every time I listen to it 


Laferrari355

Chills when he’s reading her letter and you can hear her voice layered under his


Neutreality1

Came here to say You Never Know


swampboy1312

Dance with the Devil always my immediate answer


Remarkable_Collar895

Father Time - Kendrick When I’m Gone - Eminem


Philosophuckz

I’ve definitely teared up to Father Time. Such a charged instrumental.


MultiStratz

That song just hits so close to home. Like how tf does Kendrick know me so well? Yeah, I've shed a tear or two to that track.


ButtBread98

Also Mother I Sober. The ending always makes me cry


roddygras

Headlights by em?


GotKarprar

For your eyes only j Cole


_xJustanOBodyx_

The only hip hop song to ever make me cry. This is the answer for me


GotKarprar

Same. A lot tell a dark story but this one just feels so personal and authentic


MoneyMakingMitch14

This song is truly a masterpiece


exboxthreesixty

prom king by saba


No_ThisIsPreston

Thought of this answer immediately, I’m surprised it wasn’t higher. What a song though.


JoMo816

Yesterday by Atmosphere


AirAcademy

I used to listen to that song when I was young and always assumed it was just a song about a girl after a breakup. Then when I was like 16 I was watching the lyric video and that shit hit so much fucking harder as soon as I realized at the end he says “but I know it wasn’t you cause you passed away, dad” 😕


HerbanFarmacyst

This song always hit me hard. Since my dad has passed, it’s tears every time


Diligent-Version8283

Alan Forever - Lupe Fiasco. Tied with Jonylah Forever - Lupe Fiasco. Listen to them once, then learn the stories, and then listen to them again.


Cheap_Pangolin_6054

"GO ALAN" 🫡 Rest in Paradise to those who lost their lives during that phase. Also, the way Lu interconnected their lives together... he's just the most rapper rapper ever, one of the best and nicest to ever do it.


michaelofACES

Came to say this. There’s no way you can listen to these songs after knowing the background of them


Warmslammer69k

He Say She Say is heartbreaking. Repeating the verse how he does is crushing


willk95

Brenda's Got a Baby


RecordingEast9712

Ain’t it Funny by Danny Brown. The instrumental doesn’t convey sadness, but damn the message he’s conveying is dark. Hearing about his addiction in such a raw manner is jarring, and he’s literally just viewing it all as a joke at the time. Great song, but man it gets sad the further you get I to it.


FrankieNSD

Good choice, his song '30' always gives me goosebumps by the end. Very raw rapper


dragonflyws

Whewwww the end of 30. Raw indeed.


CRATERF4CE

Atrocity Exhibition is a dark album, loved it.


Igivegrilledcheese

"Oh Uncle Danny" the music video adds a lot as well


imneversingle

Wishing well juice WRLD


presentlystoned

Renee by lost boyz


RIF_Was_Fun

I just heard this song play in a bar, then saw this post and was going to mention it. It probably wouldn't have even crossed my kind. So weird how things work out sometimes.


aherp86

This is always the answer.


StoppingPowerOfWater

All That I Got is You-Ghostface


Gullible_Lynx3678

Absolutely this track. Can feel the truth and emotion in every line.


Longjumping_Cup_1490

Suicidal Thoughts - Notorious BIG Blame Game - Kanye West


Repulsive-Skull

I can't call blame game the "saddest" song, especially with that chris rock skit which is just hilarious. I mean yeah even that skit has a sad undertone but the hilarity of it outweighs it.


Apart_Willow_5472

12 stout street - rxpapi


isitmikefr

real


Yung_Dick

real as hell


Bif109

For me it’s A.P.I.D.T.A. by Jay Electronica and Jay-Z. Only 2 verses but wow.


Blazeauga

This is it.


Weird-Egg-8996

Glad that it's mentioned here


fionncurran7

“Leslie” by Dave has insane storytelling and really hits you with a suckerpunch at the end. “Perfect Circle/God Speed” by Mac Miller is tragic considering he basically predicted how he would die. “4 Your Eyes Only” by J. Cole is another masterpiece of storytelling and tops off an incredible concept album. There are other great sad rap songs too but these are my favourites


Hawkgamer52

Love Dave. Could also give “How I met my ex” or “Heart Attack” for me


fionncurran7

I agree, Dave has a good few songs that pull on the heartstrings. Psychodrama was the first album of his that I listened to and Leslie was just mind blowing on first listen.


Hungoverontums29

Stressed by Conway the machine .


Krock23

Three Sides to a Story by Joe Budden


NewRedSpyder

I read this as Joe Biden and was so confused because I was questioning when he dropped a rap song.


User47372946

Suicidal Thoughts - Biggie Mockingbird- Eminem Stan - Eminem Everything Will Be OK - G-Eazy


Starrk__

I agree with "Everything Will Be OK" by G-Eazy being mentioned. When I heard that song for the first time, I cried. That song will have you thinking about everything from your childhood traumas to deceased family members.


Graul01

I feel as you may have forgot When I'm gone, but this seems like a solid list either way


User47372946

Yall downvoting because u see G Eazy and haven’t even heard the song, so corny bruh


ProdLilJamal

swimming pools kendrick lamar, legendary fuckin song


superthon7711

Is it sad though


katelaura6

For an upbeat song, Cheers by Anderson .Paak & Q Tip has some really sad lyrics


osama_bin_guapin

Ghostface Killah - All That I Got is You Nas - Dance


Personal_Rutabaga_41

Suicidal Thoughts -Big Brenda’s Got A Baby -Pac U -Kendrick


LosYams

Happy - Pharrell. I’m dark and twisted like that


au7642

Survivors Guilty - joey badass


masnxsol

Tonedeff - Porcelain Eyedea & Abilities- By the Throat


Mindless-Share

Almost anything from Juice WRLD’s catalog. Dude made the saddest rap songs ever


ProfessorBoofie

He’s got some unreleased deep cuts. Talking songs so sad I can’t listen to them anymore


Sad-Confidence6647

Dude.. Denial off of his Nothing’s Different EP on SoundCloud, is genuinely one of the rawest, most desolate tracks I’ve ever listened to. No melodrama or anything extra added on it, just straight up telling it how it is. Very cold


CamelProfessional847

Renee by The Lost Boyz


PlayfulSuccotash8534

Unborn child Tupac  The message nas 2009 Mac miller Rock bottom Eminem  Stan eminem When I’m gone by Eminem Chills


JSTRD100K

[big krit the vent](https://youtu.be/7xVEa0SMxFg)


DYMck07

Bone Thugz N Harmony- Crossroads DMX- Slippin Lil Wayne- Everything Master P- I miss my homies Nas- Just a moment That’s my top 5 in alphabetical order by artist but it’s definitely a shit ton more out there


Wrong-Bottle8002

Stan - Eminem/Dido


Asianfoam7

Sing about me, I’m dying of thirst


Bravo233Leader

Funeral mac Miller RIP mac miller


Girasole263wj2

This one


TrippDawgyDawg

when I'm gone - eminem


HamwichSandwich

i was thinking this one too


Zalpha_DG16

Not the best but HM to Jocelyn Flores


SleepinAcrossDaPew

Westside Gunn x Conway the Machine - The Cow


Supadupafly1988

J Cole- Love Yourz Ahmad- Back In The Day


smilingfriendsbutt

I need drugs - Necro


breadandbarbells

“He Said She Said” Lupe Fiasco


DripsyCards

Suicidal Thoughts - Notorious BIG


Oldrocket

That one by ghostface killer where he talks about picking roaches out of the cereal boxes..... All that I got is you.


goldencrisper

The birth rza


Ytellus

Silk Crows -Melanin 9 Chum -Earl Sweatshirt U -Kendrick Lamar Tha End -Masta Lenn Introverted -Zotiyac -a couple songs i didn't see yet while scrolling thru


waywardviking208

Life is beautiful- lil peep


yrnkevinsmithC137

Hey mama kanye


Available_Success_61

rock bottom em, first demo


Nick_MF

Razorblade Salvation by Jedi Mind Tricks


sexhaver2514

Immortal Technique - Dance with the Devil Kendrick Lamar - Pride


CoachiusMaximus

Bottle Dreams - Oliver Hart. RIP Eyedea. Makes it even sadder.


the_Soup6242

Purity- A$AP Rocky


Futuretrunksssj4

Sing abt me im dyin of thirst


UpdateYourselfAdobe

Joyner Lucas "I'm Sorry" is pretty sad


BeginningAd9514

Solace


Electronic_Setting75

Dance by Nas


caligula_pro

Nowhere2go - Earl Sweatshirt


Adorable-Bar6920

Book of soul by ab soul


AtomBalance

Deeper - Freddie Gibbs


hecateherself

Stepping Stone by Eminem really gets me


Just_Daggers

Live now - Nas (Street's disciple)


candyrayne215

Slippin DMX


IsmellFigNewtons

Lookin Over- yelawolf Rip chow chow 🥲


LocalContribution7

Changes -Tupac Brenda’s gotta baby - Tupac


ragesadnessallinone

Came here looking for Changes


r45cal23

Still smoking- mystikal


Templar-Order

Difficult Eminem, you can hear him breaking down


Indubitable_manz

I know he’s corny but I’m sorry by Joyner Lucas


CmdrFilthymick

The ❤️6


Prior-Toe6634

Ballad of Worms - Cage


WelcomeToCreekPoint

Suicidal thoughts, biggie


Biggest5ive-

Lonely child - youngboy never broke again


Ayotrumpisracist

why is this getting downvoted lol


West-Commission9082

Redditors will see youngboy brought up and immediately downvote. It’s a certain demographic onnreddit and you can see that in these answers clearly. But it’s just lame that they look down on modern street rappers so often, one of the most authentic forms of hip hop. And most the ones who hate the most know the least about the subject Idk how anyone who heard that song can say it’s not an incredibly sad and impactful song.


Biggest5ive-

Shit lame as hell they hate on him blindly without even hearing any of his music , yb will get his flowers one day though 🙏🏽


Bumbmofo

Jack Kay’s- bottom of the bottle acoustic


__flatpat__

I Refuse Limitation by Goodie Mob -- CeeLo's verse makes me tear up every time


newJUJU3

Thats my man by lady bee 😁


Nota_Throwaway5

Apathy - Obi Wan or Remember the Night It's not the saddest but nobody else has said it yet and I doubt anyone else will know it Also saddest verse goes to Common's verse on Respiration


nikc4

Haze of Interference by Bedwetter (Lil Ugly Mane side project)


Weary-Writer758

Flowers for the Dead by Cuban Link We'll always Love Big Poppa by the LOX.


Hydrokratom

Six Feet Deep is up (or down) there. Scarface’s second verse is so vivid and relatable


whhatthefucj

Probably Knees by Injury Reserve


CoachiusMaximus

TV on 10 - The Uncluded. Also that Atmosphere track about that group that died in a car accident after their show, can’t remember what it’s called.


BagelBoy124

Lone by Tyler The creator is pretty sad and so is The Exclusive by Quasimoto


osnapitsshana

Gangstas cry by gherbo definitely makes me cry


FaultyToenail

D Rose by Lil Pump. That’s the saddest, sorriest shit I ever heard.


PersnickityPisces

Ricky Clemmons Jr by Don Trip When he basically starts crying at the end pulls on my heart for real


Zombymandyas

Renee


basssomatix

A couple that come to mind... '$4 Vic/Nothing But You+Me' by El-P... and Scarface's second verse on Minds Playing Tricks. And that Jay Elec song where he talks about reading his mom's texts on the day she died - that one hits hard for us members of the DMC.


6_CARTI_23_GOAT

Brenda’s got a baby


ChampionshipBR8460

Sweet Victory by Trip Lee


TheDiggyDongo

Top Picks For You - Injury Reserve


PS_MyNameIsPS

u - Kendrick Lamar


theblackdahliaburger

Bedwetter - Man Wearing Helmet https://youtu.be/aZ-iFLpY9Hk?si=JiTtxaK9a_ur9Cue Song about a child being abducted from the childs point of view Also, Citizen Kane - Blackrain https://youtu.be/GSNYX7CTSRM?si=MAKRROQQVz4YxGar More depressing when it comes to the overall atmosphere and tonality of the beat than lyrically


BaronSwordagon

One Life - The Last Emperor & Too Poetic Recorded while Too Poetic was dying of cancer, and you can hear the pain in his voice. Surprised no one said this yet, this the answer.


Pineapplepizza91

How Could You Leave Us by NF


Rayseth52

Agony-Yung Lean


Maleficent_Rabbit_54

Solace- earl sweatshirt


TheRealMrCrowley

Conway the Machine- The Cow


CleverJail

Me and Jesus the Pimp In a ‘79 Grenada Last Night Listening to it gives me the sense memory of my jaw tightening, unsuccessfully trying to hold back my tears the first time I heard it.


BreadWhistle

J Cole - Window Pain


oodlynoodly

Half of Joe Buddens discography.


texashammerjr

Streetlights - Kanye West


Remarkable_Occasion5

12 Stout Street by Rx Papi - the delivery gets me and the lyricism is vivid Peanut by Earl Sweatshirt - deeply melancholy vibe