15 Of The Saddest Music Videos Ever Made

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Diddy Ft Faith and 112 – “I’ll Be Missing You”

In March of 1997, the rap world lost a legend when Christopher “Biggie Smalls” Wallace was shot and killed while out in Los Angeles. Putting his sorrow into words and then eventually dance steps, Sean “Puff Daddy/Diddy” Combs penned a song for his friend. He recruited his other Bad Boy label mates, Faith Evans and 112, and used a sample of The Police’s “Every Breath You Take” for the Biggie tribute “I’ll be Missing You.” Shot in Sydney, Australia and directed by Hype Williams, Puffy roamed the lush green countryside on a motorcycle while reminiscing about his friend. The video helped move over nine million copies of the song. That is certainly one way to mourn for a friend.

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