In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
“I’ll Be Missing You” broke music. You can pretty much date rap’s underground/mainstream schism to the moment that Puff Daddy’s performative act of mourning took over the Hot 100 and became, quite possibly, the biggest rap hit in history to that point. Underground rap had certainly existed before “I’ll Be Missing You,” but the late-’90s underground boom pretty much happened as a stern and direct rebuke to what Puff Daddy was doing. The narrative of two radically different branches of rap music — the flashy pop acts on one side and the artistic flame-carriers on the other — didn’t truly take shape on a large scale until Puffy danced to the Police in the rain.
At the same time, “I’ll Be Missing You” hypercharged conversations about sampling — not just taking pieces of old records but using those pieces to essentially remake and recontextualize songs that everyone already knew. When “I’ll Be Missing You” held down the #1 spot for almost an entire summer — in the midst of a year when Puffy and Bad Boy dominated all of popular music to a degree that hand’t been seen in decades — the Puffy approach became the focus of every conversation about where music was going. In my book — which is coming out in November and which now has a pre-order page — I’ve got a chapter about Puffy’s debut single “Can’t Nobody Hold Me Down,” since that was the first #1 hit of rap’s baroque era. But “I’ll Be Missing You” probably stands as the moment that the Puffy method reached its true dominant peak — the moment when Puffy became the main character of the whole pop-chart narrative.
One of those conversations was this old favorite: Sincere or cynical? A couple of months after the murder of Bad Boy’s biggest star, Puff found a way to capitalize on a tragedy. He rapped an ode to his late friend that took off around the globe, topping charts in countries where Biggie Smalls hadn’t even really been a known quantity. In the public eye, Puffy’s song for Biggie became an all-purpose sadness anthem — a song for anyone who ever missed anyone else. Puffy’s song also bugged the shit out of many millions of people, including many of the people who had truly loved Biggie. Puffy’s tribute was probably sincere and cynical, and it reverberated accordingly.
The song wasn’t Puffy’s. Puff Daddy had his name on “I’ll Be Missing You,” and he co-produced the track, but he didn’t have anything to do with writing the song. He didn’t even give himself a songwriting credit. This was the Puffy method writ large. With Bad Boy, Puffy brought together rappers, singers, and producers, and he put all of them to work. Puff had a central idea of what would connect, and his collaborator Mase described that idea cleanly in a couple of lines on his 1997 hit “Feel So Good”: “Take hits from the ’80s, but do it sound so crazy.” (“Feel So Good,” Mase’s highest-charting single as lead artist, peaked at #5. It’s an 8.) With “I’ll Be Missing You,” Puffy took one of the biggest hits from the ’80s, and he made it even bigger.
“I’ll Be Missing You” wasn’t part of Puffy’s five-year plan because Biggie’s murder wasn’t part of Puffy’s five-year plan. When Biggie was gunned down in March of 1997, Puff had already released his first #1 hit “Can’t Nobody Hold Me Down,” and he’d already recorded the debut album that he planned to call Hell Up In Harlem. After Biggie’s death, Puffy scrapped half of the album, changed the title, and recorded a bunch of songs that made reference to the loss of Biggie. “I’ll Be Missing You” was one of those.
Puffy wasn’t the first Bad Boy artist to record a musical farewell to Biggie. The Lox, the…
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