Throughout the decades, hip-hop has produced plenty of songs about emotional darkness. From Jay-Z to XXXTENTACION, here are 50 of the most depressing rap songs of all time.

Wielding a Sting sample and a broken heart to their most potent effect, Juice Wlrd served up a certified Sad Boy classic with “Lucid Dreams,” a breakout single that deals in paralyzing pain. His ...

The few between Drake and Kendrick Lamar got a lot of reactions from a lot of music fans. For André 3000, his reaction was sadness. In a new Crack interview, André said of the beef: “I got a little ...

The release of Doechii’s debut mixtape Alligator Bites Never Heal has cemented the ascent of a brand-new rap superstar. Unfortunately, it also resurrected a tired, misogynistic conversation among rap ...

André 3000 wasn't as enthusiastic about the Drake and Kendrick Lamar beef as everyone else was. In an interview with Kenan Draughorne for Crack magazine, the OutKast rapper was asked for his thoughts ...

The Drake/Kendrick Lamar feud was this year’s biggest rap event thus far, and it was a cause for a whole lot of excitement among many fans. But certain rap elders have expressed their disapproval of ...