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.

From XXXTentacion to Juice Wrld and more, these are the best emo hip-hop and sad trap rap songs of the last five years.

We've spoken about the best albums of the 2000s, but let's talk about the best rap songs of the 2000s. We've got some classics to cover.

Embedded in genre : sadboy, a collaborative release by rappers MGK and Trippie Redd, is an accidental lesson in what once made the collision of rap and pop-punk so electrifying.

A TikTok music producer turned "Old MacDonald Had A Farm" into an EDM-tinged rap beat. There's a whole scene of people using intentionally "goofy ahh" sounds in their music.

Power and independence remain the heartbeat of Amaarae and Kali Uchis' "Sad Girlz Luv Money (Remix)," our latest Song You Need to Know.

The Cave is the brainchild of Kenny Beats, the Connecticut-born beatmaker who might be the most vital producer in all of rap music right now. Kenny has had a strange career path.

Columns Our 10 Favorite Things in Rap This Week: Instagram Beat Battles and More Including a genuinely great TikTok trend, along with tracks by exciting young artists from Nigeria to Chicago.