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The Saddest 20 Songs in Hip Hop

November 20, 2017 by
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The hip hop genre has often been stigmatised as aggressive, braggadocios and misogynistic. Although true followers know that even though some of it can be labeled as such, there is still a range of emotions, stories, and moods that are far from the negative connotations it still struggles to shake off.

Hip hop can be used as an incredibly potent tool when telling stories and after listening to a bunch of rather glum tracks recently I was inspired to write up a list of the saddest but ultimately brilliant hip hop tracks ever.

20. Jay – Z – Song Cry
The Blueprint (2001)

This emotional charged Just Blaze track features Jay describing the pain of a long-term relationship ending, caused by his professional obligations and misguided habits.

The track was nominated for a Grammy Award for Best Male Rap Solo Performance.

“Though I can’t let you know it, pride won’t let me show it
Pretend to be heroic, that’s just one to grow with
But deep inside a ni$#a so sick.”

19. Kno ft. Tonedeff – I Wish I Was Dead
Death Is Silent

When you release an album, which is basically about death, you’d expect to hear some pretty morose tracks. This one is glum to the point of self-harm as Kno tells of a shocking incident where he is hospitalised by someone he loves. Tonedef’s verse is much darker detailing toils which have slowly taken a grip on him and left him unrepairable and worthless.

“Though I’m strong I don’t wanna live with the strain
No positive notes, no prospect glowing to give me the strength
I simply revisit the day that misery came
And, I wait for the light at the end of the tunnel, until it hits me
Like it was a train.”

18. Scarface – I Seen A Man Die
The Diary

Scarface is arguably one of the best storytellers in the game and he has been doing it since the early 90s. Here he tells the tale of a young male released from jail looking for a better life only to get dragged back into crime, robbed by his peers and left to die in a hospital while regretting his blood-soaked life – damn!

“I hear you breathin’ but your heart no longer sounds strong
But you kinda scared of dying so you hold on
And you keep on blacking out and your pulse is low
Stop trying to fight the reaper just relax and let it go.”

17. Wu-Tang Clan – Tearz
Enter the Wu-Tang (36 Chambers)

Reputedly the first song (and the saddest) recorded by the clan, Tearz is a tragic tale of street life gone wrong as well as the risks of unsafe sex. Like we hear too often in rap songs, this details the murder of a friend in cold blood and the dangers of promiscuity.

“Aw man! How do I say goodbye?
It’s always the good ones that have to die.”

16. Charlie Sloth – Come on Back to me
It’s Hard Being Good

This one may surprise a few people as Sloth is probably more known as a presenter, DJ and producer but he can also spit some decent verses. This track details a love affair which ends in tragedy. Sloth ends up losing something and someone that slowly deteriorates after being abused. Who is it or what is it?

“Then she opens her eyes a tear rolls down her cheek she tried to speak but all she could do was cry. Then she whispers everyone who’s ever said they’d loved me has used me and made me look ugly.”

15. Chino XL –
I Told You So (2001)

Not many have the same chops as Chino when it comes to metaphors and visceral wordplay. Chino XL divulges experiences of attempted suicide and depression over his relationship with his mother, girlfriend and stepdaughter over a broody head-nodder complete with wailing strings.

“Deep down, I felt that she was just another liar
Now I wouldn’t spit on her if she was on fire
Presice way to describe it, damn I shoulda been out
Our relationship a hand grenade, you just pulled the pin out.”

14. Ja Rule – Only Begotten Son
Venni Vetti Vecci

Ja’s first album was rough and hardcore unlike the other bubble-gum fodder he released, and this particularly dark track describes his relationship with his estranged father. His delivery in parts is palpable and tears are almost shed. You can’t help but feel the anguish in several lines.

“How the fuck do you sleep at night?
Knowin’ you wronged the only thing you ever did right.”

13. Tonedeff – Porcelain
Archetype (2005)

Unrequited teenage love described by one of the most uncelebrated MCs in hip hop. We’ve all had a thing for that popular girl in school, but anyone will tell you that it hurts like hell when they end up smashing your heart into little pieces.

“Yet, I waited and displayed my patience
Even offered statements of positive advice in her cases of shaky situations
But, she never associated me with hip relations
With bated breath I withstood the breakage, like porcelain.”

12. Eminem ft. Elton John – Stan
Curtain Call: The Hits 

We’ve all heard this one. Reminds us of the fragility of some people and how dangerous it is to live vicariously through others especially those in the limelight. I prefer the Elton version as Ems delivery at times is much more passionate.

“I loved you, Slim, we coulda been together — think about it!
You ruined it now, I hope you can’t sleep and you dream about it.”

11. Sadistik & Kid Called Computer – Black Rose
The Art of Dying 

There are many Sadistik tracks that could qualify for this list but this one is easier to digest than most as it’s a very relatable song about a breakup. The torment and confusion absorbed throughout the song make it difficult not to sympathise with the artist.

“Her frozen tears are streaming down the sculpted ice
Giving me the coldest bite every time I hold it tight
I’m masochistic when I love you till my heart bleeds
I’ll love you till I break when I’m running from your sharp teeth.”

10. CunninLynguists  – What’ll You Do?
A Piece of Strange (2006)

For me, this is a song about uncertainty and feeling trapped. It’s about making tough decisions and trying to escape the struggles of life but the temptation to take the easy way out can be hard to resist.

It is sad in the fact that such talented artists still struggle and they’re fortitude is constantly under pressure. There is this overwhelming sense of despair, and with Kno on the boards you know this one is going to be heavy to deal with.

“But needs outweigh cheese tryna stay in contention
‘For the love’ is a hard reason to keep my life in suspension.”

9. 2pac ft. Stretch – Pain
Above The Rim OST 

2pac rapped a lot about pain and struggle and this track is one that covers it all talking about struggles of ghetto youth, substance abuse, paranoia, poverty’s trappings and gang life. The fact that both artists on this track died in tragic ways at a young age adds another level of angst.

“My memories of a corpse, mind full of sick thoughts
And I ain’t going back to court, so fuck what you thought!
I’m drinkin’ Hennessey, runnin’ from my enemies
Will I live to be 23? There’s so much pain.”

8. Joyner Lucas – Ross Capicchioni
Along Came Joyner

Just as sad as it is disturbing, this very clever track is the true story of Ross Capicchioni trusting a friend, only to be betrayed and almost murdered by him.

“I pull out the shotty, I cocked it twice ‘till he screamed
And I shot his arm into pieces, I’m watchin’ his blood leakin’
And another shot to his chest, seen his stomach squeezing.”

Joyner Lucas raps about the story from both point of views (Ross and his “friend’s”) in this heartbreaking music video.

7. Mobb Deep – Where Ya Heart At
Murda Musik (1999)

Since Prodigy’s death, this song has gained tones of emotional weight. Along with his somber delivery, the piercing strings and Havoc’s impassioned rhymes, this is, without doubt, one of Mobb Deep’s most potent tracks.

“Have you ever lost a loved one?
You’ll never understand love ’til you lost one
Where your heart at?
I left mines’ behind wit’ my dearly departed
Now where your heart at?”

6. Brother Ali – Babygirl

This track is as heavy as a whale! The heavy subject in question is post-traumatic stress syndrome and it is described vividly by master MC Brother Ali. Ali alludes to a girl being abused as a child and tries to inspire her to carry on despite the ongoing pain.

“How can she find peace in her mind when
Love means returning to the scene of a crime?
I can feel it inside we’ve reopened wounds every time we intertwine
Such an evil design when you can’t even enjoy the sweetness you find.”

There is, however, a lot of empathy and introspection laced throughout the track which adds an extra layer of emotion – a brilliant track!

“My eyes can learn how to shine again
My inner child won’t have to hide and then
When I’m strong then love could be invited in.”

5. Nas – Undying Love
I Am… 
Nas at his storytelling best. Here he paints a tale of infidelity and unrequited love. The beginning of this track is so hopeful but ends in the most tragic way. The cop’s statement at the end also dismisses the whole tragic event, making it even more depressing. Nas’ singing on the hook is also quite lamenting.

“I never meant for this to happen, I never dreamed
This’d be my fate, such a grotesque, murder scene”

4. Fort Minor – Kenji
The Rising Tied

War is always a fertile ground to explore when it comes to tragedy and this track explores the plight of American Japanese residents during World War II. Mike Shinoda himself being of Japanese descent whose family was interned passionately talks about the horrendous experience of a man named Kenji who despite all his loyalty, goodwill and hard work is still demonised by the public in his own country.

“Now the names have been changed but the story is true
My family was locked up back in ’42
My family was there where it was dark and damp
And they called it an internment camp.”

3. Jedi Mind Tricks ft. RA Rugged Man – Uncommon Valour (A Vietnam Story)
Servants in Heaven, Kings in Hell 

Another war-related track, this time covering a very contentious and horrific one. Featuring arguably the best verse in hip hop history, the track is based on the true story of Rugged Man’s father, John A. Thorburn. Stoupe crafts an equally haunting beat that takes you to a dark and frightening place.

Rugged man throws us right into the middle of the war so vividly you can almost feel the blood splattering on your face.

“Bang bang, bullet hit my chest, feel no pain
To my left, the Captain caught a bullet right in his brain
Body parts flyin’, loss of limbs, explosions
Bad intentions, I see my best friend’s intestines.”

He also touches on the after-effects of the war ie. Agent orange. Goosebumps a plenty right here!

“I escaped the war, came back
But ain’t escape Agent Orange: two of my kids born handicapped.”

2. Immortal Technique – Dance with the Devil
Revolutionary Vol. 1 

There are countless youtube videos of people reacting to this track and my reaction was just as shocked, saddened and amazed. The most confronting part of this track aside from the vicious twist is the path the character in the song traverses, one of violence, drug abuse, murder, and gang politics. It highlights how dangerous it is to your soul if you decide to pursue a life of crime.

“So when the Devil wants to dance with you, you better say never
Because a dance with the Devil might last you forever.”

1. Cage – Ballad of Worms
Purple Rain Mix CD (2004)

Also considered to be a take on his relationship with hip hop, this on the surface is about Cages’ relationship with his terminally ill girlfriend. This is a confronting topic by itself, but Cage describes an incredibly detailed picture of the often grotesque situation and does not hold back.

“Sloppy with a fork, so Chris gotta feed her
To numb to cum, sometimes she piss while I eat her.”

The beat on this track alone makes you want to open an artery. Filled with amazing paradoxical lines, Cage’s zombie like flow and ultimately ghostly finish, the song still manages to present feelings of true love and dedication to a relationship.

“She’s barely alive and taking life from me
With no appetite but the meningitis is still hungry
Wants to make love
But I had to substitute it with holding hands while we take drugs.”

Even though a lot of the tracks here are dark, depressing and some straight up offensive, they do also remind us of what is most special. They dig up deep emotions that make us feel alive and help us empathise with our fellow human beings.

We are reminded that life is not all peachy however we are quite resilient creatures and as Tupac did say, “Through every dark night, there’s a bright day after that. So, no matter how hard it gets, stick your chest out. Keep your head up, and handle it.”

Let us know your thoughts and post any other tracks you think should have made the list.


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