The 35 Most Depressing Rap Songs

Hip-hop has been cranking out living-it-up bangers for decades, but the average historian is (or should be) aware that dark thoughts aren’t a foreign concept for the genre. After all, Grandmaster Flash & the Furious Five’s 1982 classic “The Message” wasn’t exactly a joyful number. The bleakness feels natural for a culture that grew out of urban plight and the trauma of impoverished people of color; it makes sense that at least some of the lyrics reflect those misfortunes and their lasting effects on the psyche.

Still, treating that pain as a mental health issue has been a recent development. Jay Z—who once rapped about being hard in the pursuit of hard cash in 1996’s Reasonable Doubt—became one of the main voices of that shift during the 4:44 campaign. “Three of your brothers are dead and your mother used to beat you,” he said in one of his Footnotes episodes. “You need help. Someone needs to talk you through why you’re feeling these feelings.”

Many other rappers have embraced vulnerability in recent years, including Freddie Gibbs, Kanye West, and J. Cole—even when male emotional introspection and mental health weren’t part of the dominant narrative. Company Flow’s classic Funcrusher Plus notably took a break from dense rhyming for El-P to hauntingly remember his abusive stepfather. Kendrick Lamar’s “u” explicitly reveals his pain behind closed doors—being the greatest rapper in the world can only heal so much (Lamar on the song: “That was one of the hardest songs I had to write....That shit is depressing as a motherfucker. But it helps, though. It helps”). Then there’s the personal dispatches from the hedonistic realms of Future and Lil Wayne.

Like anyone else, the rappers and hip-hop artists of our day are dealing with their own shit; what better way to express themselves then to hop on the mic and vent about it? This is our round-up of the most depressing rap songs.