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Home Entertainment Music

5 of the Darkest, Most Depressing Rap Songs of All Time

November 4, 2025
in Music, News
5 of the Darkest, Most Depressing Rap Songs of All Time
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One of the most beautiful things about hip-hop is that it can be a form of escape. Rapping works the same way other art does, a vessel in which to hone creative expression, the good and the dark alike. How do we channel our experiences and hone it into something honest and true? Hip-hop has always been good for this, be it mundane and breezy or something much darker and sadder.

Rapping through the hard times has been true of hip-hop since Grandmaster Flash made “The Message.” Conveying the harsh realities of the world allow others to relate or it’s just a way for the artist to work through their pain and mental health. So Noisey cobbled together five of the most depressing rap songs of all time to demonstrate how gracefully hip-hop has tackled the bad times. That way, we know we’re not alone when battling through the storm.

Five of the Most Depressing Rap Songs Ever

DMX – “Slippin”

DMX’s story is like a modern day Job. The bible saw Job grapple with an unprecedented amount of tragedy all at once and repeatedly. All because the devil made a wager that he would crack and turn his back on God. X was abused and isolated, betrayed by his mentor, and grappled with a lifetime of addiction. Ultimately, both stories are a matter of endurance.

All of this culminates on “Slippin,” a devastating insight into why DMX often found himself in legal and personal drama. “I used to have to puff my L in the morning before I could fly,” he sighs. X is desperate to numb himself for a while and explains in brutal detail why. But by the end of the song, he offers himself a glimmer of light. If he could be strong enough for his kids, it’ll all be worth it. Darkness may have been at the core of DMX but it never consumed or defined him by the end of his life.

2Pac – “Brenda’s Got a Baby”

To think 2Pac conjured this song from reading a story in the newspaper. Pac has never shied away from the dark and difficult matters of the world and he always did it with such grace. “Brenda’s Got a Baby” is another example of this, a fictional tale surrounding a pregnant teenager with no foundation at home due to addiction and abandonment. 2Pac really captures the complexity of Black and poor folks, showing how vicious of a cycle the system has perpetuated.

UGK – “One Day”

A sobering tale of mortality, “One Day” grapples with the suddenness that comes with death. You could talk to someone and they look fine and healthy. Then, the next day, they could be gone. They could’ve been killed or they could’ve had an illness we never knew about. All we know is that they’re gone and there is no going back to fix anything. It’s the survivor’s guilt that creeps up on us, all accentuated by the howls of grief on the Ronnie Spencer hook.

Ab-Soul – “The Book of Soul”

Losing Alori Joh radically changed Ab-Soul’s life. In February 2012, she died by suicide after jumping off of a radio tower. “The Book of Soul” depicts the love and romance between Joh and Soul, all to culminate in absolute tragedy. Ultimately, it leaves Ab-Soul in tatters, on the brink of giving up entirely. “Everything I love the most gets taken away, my momma and music is next. And if that happens before I turn 28, then I’m going out with Kurt Cobain,” he solemnly raps. A haunting rumination on grief and how it torments the idea of faith and the desire to go on at all.

Bone Thugs-n-Harmony – “Tha Crossroads”

“I miss my uncle Charles y’all” has become one of the most memorable lines in hip-hop history. The fact it’s such a touchstone in culture robs “Tha Crossroads” of some of its emotional impact. But when you examine the record, it’s one of the most depressing wails of grief in music history. Death haunts the record and Bone Thugs-n-Harmony never quite have the answers to their grief. All they know is that one day, they’ll reunite at the crossroads, the final piece of life.

The post 5 of the Darkest, Most Depressing Rap Songs of All Time appeared first on VICE.

Tags: hip-hopMusicNoisey
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