Posted by , Sep 9, 2014 at 03:42pm
In honor of the Sad Boys movement, we look through the back catalog of real hip-hop to determine who were the original tragic figures in hip-hop and what were their saddest songs.

I don't know where you were when the sad wars hit, but if Yung Lean and his Sad Boy affiliates ushered in an era where 15-year-old Swedish kids crying over pokemon cards, clad in North Face, are spawning articles in swanky East Coast outlets, now seems like the time to honor the tradition of hip-hop tear jerkers that broke your heart but didn't actually make you cry that one time. That was just something in your eye, right? No, it was allergies, wasn't it?

Alright, whatever. The point is that the lyrical nature of rap makes for some heart-wrenching confessionals. We like our rappers to be bad-ass, sure, but if they never creep up from under the shell of super-sized hip-hop braggadocio and tough-guy bullshit with all the pathos of a cartoon lampooning the general public image of a rapper, we tend not to remember them all too well.

Fortunately, we've waded through some of the most thoroughly depressing bars out there, giving you the opportunity to feel pretty horrible too. Without further ado, here's a list of a few of the saddest rappers and their saddest songs that will leave you wallowing in your own misery more than some sweater-vest wearing nerd from the eighties ever did when listening to Morrissey croon ambiguous bummers.

Let us know what we got right and, let's face it - this is more tempting, what we missed.

Sadboys: The Saddest Rappers & Their Saddest Songs

In honor of the Sad Boys movement, we look through the back catalog of real hip-hop to determine who were the original tragic figures in hip-hop and what were their saddest songs.


I don't know where you were when the sad wars hit, but if Yung Lean and his Sad Boy affiliates ushered in an era where 15-year-old Swedish kids crying over pokemon cards, clad in North Face, are spawning articles in swanky East Coast outlets, now seems like the time to honor the tradition of hip-hop tear jerkers that broke your heart but didn't actually make you cry that one time. That was just something in your eye, right? No, it was allergies, wasn't it?

Alright, whatever. The point is that the lyrical nature of rap makes for some heart-wrenching confessionals. We like our rappers to be bad-ass, sure, but if they never creep up from under the shell of super-sized hip-hop braggadocio and tough-guy bullshit with all the pathos of a cartoon lampooning the general public image of a rapper, we tend not to remember them all too well.

Fortunately, we've waded through some of the most thoroughly depressing bars out there, giving you the opportunity to feel pretty horrible too. Without further ado, here's a list of a few of the saddest rappers and their saddest songs that will leave you wallowing in your own misery more than some sweater-vest wearing nerd from the eighties ever did when listening to Morrissey croon ambiguous bummers.

Let us know what we got right and, let's face it - this is more tempting, what we missed.

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