3 of the Darkest, Most Depressing ’90s Rap Songs

To many, the ’90s were the golden age of rap. From Dr. Dre to Nas, Jay-Z, Wu-Tang, The Fugees, DJ Shadow, The Roots, and Missy Elliott, the era had it all. There were creative highs, iconic songs, memorable albums, and even some mainstream recognition of underground backpack artists those truly in the know already adored. What wasn’t to love?

But with all those positives came some negatives. There were a few songs released during the decade that sent chills up the spine. And here below, we wanted to examine several of those offerings. Three songs in particular that were sad and bleak, even worrisome. Indeed, these are three of the darkest, most depressing rap songs from the ’90s.

“’97 Bonnie & Clyde” – Eminem from The Slim Shady LP (1999)

When Eminem released his debut major label record, The Slim Shady LP, in 1999, the world of rap music changed forever. He was clever, sharp-tongued, and impossible to hold back. With iconic rap producer Dr. Dre behind him, Em took aim at everyone from boy bands to pop stars to members of his own family. But it got pretty dark when he started writing songs about killing his ex and the mother of his daughter. That’s exactly what “’97 Bonnie & Clyde” is all about. Not exactly gentlemanly stuff. It’s all pretty sadistic and dark.

“Suicidal Thoughts” – The Notorious B.I.G. from Ready to Die (1994)

Before Eminem, there was The Notorious B.I.G. Sadly, the career of one of the greatest pure lyricists of all time was seemingly destined to end prematurely. The artist’s literal debut studio album is called Ready to Die. And one of the most intense tracks on the LP is the song “Suicidal Thoughts.” In some reviews, the offering was likened to the death of Nirvana frontman Kurt Cobain. And on it, Biggie talks about his own suicide. The final track on the album ends the LP with a morbid, nasty touch.

“Brenda’s Got a Baby” – Tupac Shakur from 2Pacalypse Now (1991)

One of rap’s most sensitive rhymers was also one of its most fiery. Tupac Shakur, who was at the center of the tragic East Coast/West Coast rap battle that ended in bloodshed, was as observant as any poet and as forceful as any pipe bomb. His 1991 song, “Brenda’s Got a Baby,” paints a bleak picture of a teenage girl now forced into motherhood. There is a lot of talk from people about being “pro-life,” but that means taking care of those who are suffering, too. Tupac tells an all-too-common story of the street on this sad but classic track.