The 12 Most Depressing Hip Hop Tracks

Puff Daddy feat. Faith Evans & 112 – “I’ll Be Missing You”

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Power 105.1’s Powerhouse 2005: Operation Takeover
Credit: Scott Gries/Getty Images

Diddy loved to turn up and get the party going, but when his close friend, The Notorious B.I.G., was murdered, he created one of the saddest rap songs ever.

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