The Notorious B.I.G.'s death shocked the music world in the spring of 1997. Only a few months later, his friend and label executive Sean "Puffy" Combs shared his feelings through song - and scoring one of the year's best-selling singles.
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"I'll Be Missing You" united Puffy, Biggie's widow Faith Evans and R&B trio 112 in a heartfelt memorial to their fallen friend. In classic Bad Boy fashion, the track flipped a classic pop hook - in this case, the guitar riff from The Police's chart-topping 1983 single "Every Breath You Take."
"When I made the record, I was finally able to talk to him," Puff said of the track. "That's all it was, a conversation."
Backed by a Hype Williams-directed video filmed mostly in Chicago, "I'll Be Missing You" was an out-of-the-gate smash, becoming one of the first songs in history to debut at No. 1 on the Billboard Hot 100. (It stayed there for 11 weeks, eventually being replaced by a Biggie single, "Mo Money Mo Problems.") Only weeks after it dropped from No. 1, Puff Daddy, Evans and 112 came together to perform the song at the MTV Video Music Awards, complete with a cameo from Sting, who wrote "Every Breath You Take."