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Introduction: For every positive there is a negative and this applies to every area in life, including our much beloved hip-hop/rap world. Hip-hop is known for its arrogance, ruthlessness and excessive materialism. However despite all these topics rappers at time dig deep within their inner souls to give us tracks that are personal or even in the perspective of someone else that tackle the sadness and ills of life. This list looks at 808sandblues saddest/depressing songs that we have ever heard and trust me we have heard every sad rap song in existence. Only few have managed to make us cry and leave a lasting impact on us and they make it on this list.

10

Kanye West – Roses

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Artist: Kanye West

Album: Late Registration

Release Date: 30 August 2005

Song Length: 4:05

Everyone knew from Kanye’s debut album The College Dropout that he was a man full of confidence and arrogance. But his following album Late Registration showed us a side of Kanye that we thought we would never see on a Kanye West album. Kanye is vulnerable on Roses as the song tells the story of his grandmother’s near death experience. Anyone who has been at the hospital and praying that your loved one makes it, this song hits home. Kanye and his family are faced with one thing certain in this life, death and he really isn’t ready to handle the death of this Grandma, she’s still got a bunch of roses to smell. Thankfully his grandma makes it through but the whole experience was terrifying for Kanye and his family.  Kanye West isn’t known for making sad songs, but he’ll never make a sadder song than roses no matter how hard he tries.

Key lyrics

If she gon’ pull through, we gon’ find out soon
But right now she asleep, sleep, sleep
My momma say they say she could pass away any day
Hey chick, what these doctors know anyway?
Let me see the X-rays, I ain’t no expert, I’m just hurt
Cousin Kim took off of work
Plus my Aunt Shirley, Aunt Beverly, Aunt Clay and Aunt Jean
So many Aunties we could have an Auntie Team
Feel like Amerie, it’s just “One Thing”
When they said that she made it you see they eyes gleam
I think we at a all-time high
To get there, we run, we fly, we drive
Cause with my family we know where home is
And so instead of sending flowers, we’re the roses

9

Lupe fiasco Featuring Gemstones & Sarah Green – He Say She Say

Artist: Lupe Fiasco

Album: Food & Liquor

Release Date: September 19 2006

Song Length: 4:12

Lupe Fiasco’s He Say, She Say sheds light on one serious American issue, single parenthood. This song tells the story of a father leaving his son and of the consequences of a father abandoning his family. This is a heartfelt and personal song because of how applicable it is to the African-American community where 72 percent of Black children are raised in a single parent household. Michael Young History is abandoned by his father, and his mother is left to raise her children by  herself in the ghetto. This is the beginning of the course of events which concludes sadly with his death on The Cool, Lupe’s second album. The chorus is up there with some of the most powerful lyrics I’ve ever heard.  Contrasting views where the mother doesn’t want his son to grow up without a father and The father doesn’t know what the mother wants from him.

Key lyrics

I can’t, I won’t, I can’t, I won’t
Let you leave
I don’t know what you want
You won’t want from me?

8

P. Diddy Featuring Faith Evans & 112 – I’ll Be Missing You

Artist: P.Diddy

Album: No Way Out

Release Date: May 27 1997

Song Length: 5:43

You couldn’t go anywhere in the late 1990s’ without hearing this song. Biggie died in March 1997 and three months later that year Diddy released this heartfelt song as a tribute to the legendary status. Excellently sampled from The Police song “Every Breath You Take, this song went on to break numerous rap records and subsequently immortalised the legend of B.I.G.

Key Lyrics

Every day I wake up, I hope I’m dreamin’
I can’t believe this shit
Can’t believe you ain’t here
Sometimes it’s just hard for a nigga to wake up
It’s hard to just keep goin’
It’s like I feel empty inside without you bein’ here
I would do anything man, to bring you back
I’d give all this shit, shit the whole lot
I saw your son today, he look just like you
You was the greatest, you’ll always be the greatest
I miss you B.I.G

7

Tupac Featuring Outlawz – Starin’ Through My Rear View

Artist: Tupac

Album: Gang Related – The Soundtrack

Release Date: October 1997

Song Length: 5:07

Tupac’s most underrated song is also his most depressing. Tupac explains that life is a game and the game of life is to be played to the fullest. So if you want to be a player and beat the game, you have to go on and forget the past and failures. If you live in the past & worry about all the fucked up things that happened and ask God why? You are not going to get an answer.  If you play game by its rules make sure you play to win. That is Pac’s massage for his listeners. Now Pac himself is driving towards his own future, looking back at the old world and leaving it behind him, along with the people who don’t know how to play or don’t have that mindset. However Pac does not want to leave his past life and it is because of that he ends up getting killed. ‘They got me starin’ at the world through my rearview. Go on, baby, scream to God,he can’t hear you. I can feel your heart beatin’ fast ’cause it’s time to die’ is errie and chilling as Pac predicts his own death.

Key lyric

They got me starin’ at the world through my rearview
Go on, baby, scream to God, he can’t hear you
I can feel your heart beatin’ fast ’cause it’s time to die
Gettin’ high, watchin’ time fly
And all my motherfuckers
Starin’ at the world through my rearview
Go on, baby, scream to God, he can’t hear you
I can feel your heart beatin’ fast ’cause it’s time to die
Gettin’ high, watchin’ time fly
And all my motherfuckers

6

Bones Thugs-N-Harmony – Crossroads

Artist: Bones Thugs-N-Harmony

Album: E.1999 Eternal

Song Release Date: April 1996

Song Length: 5:07

It is mandatory for everyone to have this song on their all time saddest rap songs list. Crossroads is a heartfelt tribute to NWA member Eazy-E who died of Aids in 1995.  It is their biggest selling single, reaching number one on the Hot 100 (one of two rap songs on this list to do so, the other being ‘I’ll Be Missing You’ by P Diddy), and in 1996, the song won a Grammy for Best Rap Performance by a Duo or Group. The hook on this song is perfect and it’s impossible to not sing along and cry when the song is playing. Crossroads is about life and death and how it effects people all over the world. What makes this song so special is that we can all find Solace in it because life on this earth is temporary and short, and when we die we’ll meet our lost ones.

Key Lyrics

Lil E-Z long gone
Really wish he could come home
But when it’s time to die, gotta go, bye bye
All a lil’ thug could do was cry, cry
Why’d they kill my dog?
Damn, man, I miss my Uncle Charles, y’all
And he shouldn’t be gone
In front of his home, what they did to Boo was wrong
Oh so wrong, was so wrong
Gotta hold on, gotta stay strong
When the day comes
Better believe Bone got a shoulder you can lean on, lean on

 5

Kendrick Lamar – Sing About Me, Im Dying of Thirst

Artist: Kendrick Lamar

Album:  Good Kid, M.A.A.D City

Song Release Date: October 2012

Song Length: 12:03

Coming in at number five is Kendrick Lamar’s 12:03 epic where Kendrick raps in the perspective of three individuals growing up in Compton.

Sing About Me, I’m Dying of Thirst is the centrepiece of his second classic album. The first verse, Kendrick raps in the perspective of Dave’s brother after Dave’s death. Dave’s brother argues that Kendrick is at fault as they were retaliating based on an incident that happened to Kendrick.  But he appreciates Kendrick for being there for Dave and holding him in his arms when he was dying.

The second verse, is from the perspective of Keisha’s sister, a woman who was mentioned in Section.80. Keisha is now a prostitute after years of being molested and she is now dead.  Keisha’s sister condemns Kendrick for putting Keisha on blast, without knowing her that well.  She now follows her sisters path of prostitution in order to survive.

The third verse, is from Kendricks own perspective as he raps about his infatuation with death. Kendrick also reflects on the previous verses and ends his verse by asking his listeners if he has put enough work into his music to be worth singing about. This song is not for the weak-willed and faint hearted because once you immerse yourself into the song tears will fall.

Key lyrics

Sometimes I look in the mirror
And ask myself: Am I really scared of passin’ away?
If it’s today, I hope I hear a
Cry out from Heaven so loud it can water down a demon
With the Holy Ghost ’til it drown in the blood of Jesus
I wrote some raps that make sure that my lifeline reekin’
The scent of a reaper, ensurin’ that my allegiance
With the other side may come soon, and if I’m doomed
May the womb help my mother be blessed for many moons
I suffer a lot
And every day the glass mirror get tougher to watch
I tie my stomach in knots
And I’m not sure why I’m infatuated with death
My imagination is surely an aggravation of threats
That can come about, ’cause the tongue is mighty powerful
And I can name a list of your favorites that probably vouch
Maybe ’cause I’m a dreamer and sleep is the cousin of death
Really stuck in the schema of wonderin’ when I’ma rest
And you’re right, your brother was a brother to me

4

Immortal Technique – Dance with the devil

Artist: Immortal Technique

Album:  Revolutionary Vol.1

Song Release Date: September 2001

Song Length: 6:49

This depressing track should always be in this discussion when it comes to lists like these. It is arguably one of the most messed up tracks in the history of Hip-Hop, backed by a melodic piano sample and later on hard hitting drums, this song is haunting, bleak, dark and downright depressing. It tells the story of a young kid who desperately wants to join a gang and he is forced to prove himself. The following events happen, unprovoked violence, theft, drug abuse, peer pressure, grief, gang rape, guns, suicide and concludes with his suicide after realising that he raped his mother.

Key Lyrics

I once knew a nigga whose real name was William
His primary concern was makin’ a million
Bein’ the illest hustler that the world ever seen
He used to fuck movie stars and sniff coke in his dreams
A corrupted young mind at the age of thirteen
Nigga never had a father and his mom was a fiend
She put the pipe down, but for every year she was sober
Her son’s heart simultaneously grew colder
He started hangin’ out, sellin’ bags in the projects
Checkin’ the young chicks, lookin’ for hit-and-run prospects
He was fascinated by material objects
But he understood money never bought respect
He built a reputation, ’cause he could hustle and steal

3

The Notorious B.I.G. – Suicidal Thoughts

Artist: Notorious B.I.G.

Album:  Ready to Die

Release Date: September 13 1994

Song Length: 2:50

Biggie begins Ready to Die with such confidence on the mic that we had not seen since Rakim’s Paid in Full album. He tells us about his life growing up and the life of a superstar rapper. Excessive sex, coming up from poverty, drugs, partying and oh receiving oral sex on a skit make up most of the album, so you’d never expect the album to end with a song called Suicidal Thoughts. On Suicidal thoughts, Biggie calls up Puff Daddy in the middle of the night to explain to him that he’s about to commit suicide. which somehow makes the song more chilling and surreal This song offers a moment of reflection and captures the existential despair of a morally conflicted young man, confined to his metaphorical four-cornered room . We see a moment of weakness, extreme in its intensity, biggie ashamed of all his guilt, feeling unloved by the women in his life shame and sins he pulls the trigger to end his own life. Bleak indeed.

Key lyrics

When I die, fuck it, I wanna go to hell
‘Cause I’m a piece of shit, it ain’t hard to fuckin’ tell
It don’t make sense, goin’ to heaven with the goodie-goodies
Dressed in white, I like black Timbs and black hoodies
God’ll prob’ly have me on some real strict shit
No sleepin’ all day, no gettin’ my dick licked
Hangin’ with the goodie-goodies, loungin’ in paradise
Fuck that shit, I wanna tote guns and shoot dice
(You talkin’ some crazy shit now, nigga)
All my life I been considered as the worst
Lyin’ to my mother, even stealin’ out her purse
Crime after crime, from drugs to extortion
I know my mother wish she got a fuckin’ abortion
She don’t even love me like she did when I was younger

2

Nas – Dance

Artist: Nas

Album:  God’s Son

Release Date: December 13 2002

Song Length: 3:34

Nas’ mother passed away a few months before the release of his album God’s Son. This song is dedicated to his mother, and serves as one of the closing tracks of the album. The hook on this song is cuts you emotionally because of how relatable this song is, even if your mother is still alive. Nas is a master in making songs that cut through the heart of a listener and he hits the ball here. At the end of the song, Olu Dara, Nas’s father, plays the cornet as a tribute to his fallen spouse.

Key lyrics

I dream of the day I can go back to when I was born
Layin’ in your arms, wishin’ you was here today, Mom
Wish you’d appear, just for a second from Heaven
My tears would be gone, I wouldn’t be rappin’ this song
I’d be happy drivin’ up to your eight-bedroom mansion
Up late, laughin’ about the hard times we faced
The galaxy is so enchantin’ beyond, Galileo’s understandin’
Past the Milky Way and all the planets
There’s somethin’ out there greater, but only God knows
Scientists claim we came from apes, but they lies though
That was part of our conversation

1

 Ghostface Killah – All that I Got is You

Artist: Ghostface Killah

Album:  Ironman

Release Date: September 22 1996

Song Length: 5:20

This criminally underrated song by rap legend Ghostface Killah tops our list of the top 10 saddest/depressing rap songs. All I Got is you details his childhood and the struggles his mom went through to raise him.  He raps about growing up in a poor family in the Stapleton Housing Projects, watching his father leave their family at the age of six, not being able to afford toilet paper and having to use newspapers to clean himself, sharing a small bed with three other siblings and living with fifteen other family relatives in a three bedroom apartment, picking roaches out of water-filled cereal and going next door to borrow leftover bread from neighbors. This reminds us that we should always appreciate what we have in life, just because your parents can’t afford a ferrari don’t mean you have it bad in life. Many others are living in terrible conditions in this unfair capitalistic world/system. There is much more that needs to be done so everyone can live a fulfilling live free from poverty. Great reflective song from Ghostface Killah.

Key lyrics

Seven o’clock, pluckin’ roaches out the cereal box
Some shared the same spoon, watchin’ Saturday cartoons
Sugar water was our thing, every meal was no frills
In the summer, free lunch held us down like steel
And there was days I had to go to Tech’s house with a note
Stating “Gloria can I borrow some food I’m dead broke”
So embarrasin’ I couldn’t stand to knock on they door
My friends might be laughin’, I spent stamps in stores

Mommy where’s the toilet paper, use the newspaper
Look Ms. Rose gave us a couch, she’s the neighbor

Conclusion: Thanks for reading. Do you agree with our list? tell us what you think and write your own list in the comment section below.

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2 Comments »

  1. This is a great list. I think Immortal Technique’s ‘You Never Know’ from Rev. Vol 2 hits a bit harder for me. Dance With the Devil is such a shocking song, it hardly gives me room to feel sad because all I can thinks is… Wow, damn.

    Everything on this list is on point though.

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