I Can’t Go to Sleep: A History of Sad Rap

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By Craig Jenkins

Last month we introduced you to Little Pain, the Brooklyn rapper at the forefront of the sad rap movement. Little Pain, along with Scandinavian teen sensation Yung Lean Doer and his Sad Boyz collective, touts a brand of cloudy lo-fi rap that pridefully catalogs personal turmoil the way A-list MCs flaunt their riches. “SMH (Broke Boyz Anthem)” is all about Pain moping around with no cash save for the dollar prints in his durag, and Yung Lean’s “Ginseng Strip 2002” finds the 16-year-old spouting self-deprecating non-sequiturs about sexual encounters with coked out Zooey Deschanel look-alikes. There’s a fine chance this is all an act—both Lean and Pain skirt the same line of ostensible disingenuousness that guys like Lil B and Riff Raff have been blurring for the last few years—but now that it’s spawning songs like Lean’s low-key scintillating “Gatorade,” it might be time to take a look at how we got here.

Hip-hop has never been too cool for despair; one of the genre’s earliest hits was Grandmaster Flash & the Furious Five’s 1982 classic “The Message,” a grave story song about trying to maintain your cool in a hopeless place. A year later Melle Mel dropped “White Lines (Don’t Do It),” which criticized the era’s dangerous dalliances with cocaine. But songs like these were outliers in a genre still very much enamored by the party scene that birthed it. It would be a few more years before rappers started weaving their own autobiographical ills into their rhymes, and it wasn’t until recently that mainstream MCs started wearing these troubles like badges of pride. Here’s a history of some of the artists that laid the groundwork for the birth of sad rap.

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