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.

Meet Andy Grammer Andy Grammer is a singer, songwriter, and record producer. He’s best known for his song, “Honey, I’m Good,” which peaked at number 9 on the Billboard Hot 100.

Kameron Marlowe, a self-admitted happy person, is enamored by sad songs and finds that he writes more sad songs in a year than any other song.

The '90s are often the decade people talk about when they talk about the golden era of modern country music, but the 1980s were no slouch, either. And when it comes to sad songs, the '80s provided ...