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10 Most Depressing Rappers of All-Time

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In the mid 1990’s when Hip-Hop hop was transitioning out of its Golden Age, there were dozens of emcees making millions off of their pain and misery. At one point 2PAc was infuriated at the Notorious B.I.G. and stated the Biggie took his gory “Ready to Die” manifesto from him. Pac stated that Biggie Smalls style was all “Party and BullShit” and after their encounter his rhymes began to take a deep-dark spin. On the track You’re Nobody (Til Somebody Kills You) Biggie raps: “With my Sycamore style, more sicker than yours Four-four and fifty-four draws.”

I’m no longer a confused sixteen your kid living my life through my favorite rapper, but In my opinion you are not a great rapper if I haven’t felt your pain. Truth be told, there is nothing like music that can switch your mood in the blink of an eye. With that being said, here is a list of the 10 Most Depressing Rappers of All-Time.


10. Kid Cudi

When Kid Cudi bursted on the scene with “Day and Night,” he united the lonely stoners worldwide. Since then, Scotty has been keeping us numb with his brand of new wave emo rap….


9. Tyler Creator

ODD Future’s most vocal member, Tyler the Creator is the definition of Kray like a a Fox. With legions of fans globally, Tyler has this new generation of music listeners eating out of the palms of his “Stans.”


8. Beanie Sigel

From Phili to the “Rock”, Beanie Sigel has consistenlty laced up with rhymes guns and street life. Listen to the Reason and you will see why Beans takes the #2 spot on our list of the 10 Most Depressing Rappers of All-Time.


7. The Game

Evernthough California is known for sunny weather and bomb trees Jayceon Taylor is always giving his listeners a dose of pain and drama.


6. Scarface

Brad Jordan is the definitive definition of a gory MC. From his Gheto Boyz to “Emeritus,” Scraface is the go to rapper when you are looking for a fix.


5. Eminem

Eventhough Eminem is the biggest sellign rapper of all-time, he is still one of the most depressing emcees to bless the mic. “I’m sorry mama. I never meant to hurt you. I never meant to make you cry. But tonight, I’m cleaning out my closet.”


4. Immortal Technique

The first time I heard Immortal Technique I was shocked by the vivid imagery of death in murder. In the classic song “Dance With The Devil,” Technique tells the story of a sex, murder and more mayhem…..


3. DMX

Dark Man X AKA Earl Simmons was the first rapper to have to multi platinum albums in one year. At one time, Jay-Z knew in order to become the most powerful man in on Def Jam Records he would have to beat DMX. Peep, “it’s Dark and Hell Is Hot” and you will see why DMX is #3 on our list of the 10 Most Depressing Rappers of All-Time.


2. Zero and Joe Budden (Tie)

When it comes to making “mood music”, the Mo City Don and Joe Budden are the Kings of Sad ballads that turn sunny days into rainy ones. In the underground classic “I Hate You,” Zero raps “You picked a fine time to leave me, now this house aint a home had no problem being faithful; I love you so much I hate you.” Proof of Joe Budden’s dark twist of rap can be found in his epic “Mood Muzic” mixtape series.


1. Tupac

When it comes to emcees, 2Pac is the holy grail for all rappers looking to cement themselves in Hip Hop’s “Hall of Fame.” In. addition, Tupac is the one rapper who can totally switch your mood in a millisecond.

  • Bic

    what a shit list