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 harder-than-cinderblocks Yonkers trio who started their career on Bad Boy, hit on the idea first, and they came out with the clumsy-but-sincere street single “We’ll Always Love Big Poppa.” It’s not a great song. There’s a static kids’ choir and a truly goofy sign-off line from Sheek Louch: “Christopher Wallace, Frank White, holding it down/ I guess you with the real King of New York now.” He’s talking about God. Biggie had called himself “the Black Frank White” in reference to Christopher Walken in Abel Ferrara’s King Of New York, but God is the real King of New York. (The Lox’s highest-charting single as lead artists, the anthemic 1998 Lil Kim/DMX collab “Money, Power & Respect,” peaked at #17.)
Puffy hadn’t really considered recording his own Biggie farewell until after he heard “We’ll Always Love Big Poppa.” In Fred Bronson’s Billboard Book Of Number 1 Hits, Puff discusses what was in his mind in that time: “When I was dealing with all the funeral arrangements and was out of the loop on what was going on [at Bad Boy], one of my acts made a tribute record. I said, ‘I gotta do this, too.’ I felt it was something that would help me.” Presumably, he’s saying that it would help him psychologically. Maybe it did. It definitely helped his career.
As everyone reading this already knows, Puffy paid his respects by sampling the living shit out of the Police’s 1983 mega-smash “Every Breath You Take,” which was not exactly a sincere, devotional ballad. Sting wrote the Police’s only Hot 100 chart-topper from the perspective of a deranged, controlling stalker; it’s an anti-love song. When “I’ll Be Missing You” became even bigger than the Police’s original, lots of people had fun pointing out that Puffy had gotten the original song’s idea wrong. To my mind, that whole line of thinking misses Puffy’s point. Puffy didn’t misinterpret “Every Breath You Take” when he made “I’ll Be Missing You” any more than he misinterpreted Grandmaster Flash & The Furious Five’s “The Message” when he made “Can’t Nobody Hold Me Down.” In both cases, Puff simply flipped those songs’ meanings. That’s how sampling works. You take an existing thing, and you turn it into something else.
In the Bronson book, Puffy talks a bit about why he used the “Every Breath You Take” sample: “That’s always been one of my favorite songs. It’s always made me cry. It always made me think of my father, in a good way.” Puff Daddy’s father, a Harlem numbers runner and drug dealer, was shot to death when Puffy was three years old. “Every Breath You Take” topped the Hot 100 when Puffy was 13. In the Bronson book, Puffy says that he’d get his TV privileges taken away whenever his mother punished him, so he’d listen to the radio instead. Picture a 13-year-old kid stuck in his room in Mount Vernon, grounded, thinking about the father who he can barely remember, listening to a stalker ballad on the radio and crying to himself. Puffy didn’t get “Every Breath You Take” wrong. Instead, when he was a kid, he took what he needed to take from this song. Years later, as a superstar producer, he did the same thing.
Puffy co-produced “I’ll Be Missing You” with Stevie J, the Bad Boy in-house producer who’d also co-produced “Can’t Nobody Hold Me Down.” Puffy also brought in a couple of familiar Bad Boy faces to help out on the song. Faith Evans was Biggie’s widow, and she was a star in her own right. Faith, born in Florida and raised in New Jersey, grew up singing in church. She studied marketing at Fordham before dropping out when her daughter Chyna was born. For a little while, Faith worked as a backup singer for the R&B star Al B. Sure!, and that’s how Puffy heard her. When Puffy launched Bad Boy, Faith was the first woman that he signed. She sang backup on Puffy-produced records for artists like Mary J. Blige and Usher, both of whom will eventually appear in this column. In 1995, Faith released Faith, her debut album. It went platinum, and a couple of singles charted. The ballad “Soon As I Get Home” was her biggest early hit; it peaked at #21 on the Hot 100.
Faith met Biggie Smalls at a Bad Boy photoshoot in 1994, and the couple got married a few days later. Their son Christopher Wallace, Jr. was born in 1996. By that time, though, Biggie and Faith were fully estranged. Biggie carried on public affairs with proteges like Lil Kim and Charli Baltimore, and Tupac Shakur’s claim that he’d had sex with Faith was a big point of contention during Pac’s feud with Biggie. By the time Biggie died, Faith had already started dating Todd Russaw, the record exec who would become her second husband.
Faith Evans’ wounded, heartfelt vocal is probably the best thing about “I’ll Be Missing You.” Maybe she and Biggie weren’t in a great place when Biggie died, but I don’t have any reason to doubt Faith’s sincerity on that song. It’s really hard to lose somebody, even if you sometimes hated that person in life. (I just lost my dad, so this is a little more obvious to me now than it ever was before.) On the bridge of “I’ll Be Missing You,” Faith abandons the melody of “Every Breath You Take” and instead sings a reworded version of “I’ll Fly Away,” the gospel standard that the former sharecropper and shape-note composer Albert E. Brumley wrote in 1929. For me, that’s the moment that “I’ll Be Missing You” comes closest to taking flight.
That bridge also features 112, the male R&B group that was also part of Puffy’s Bad Boy roster. 112 formed in the early ’90s, when a bunch of Atlanta high school friends started singing together. They called themselves Forte at first, and they impressed Puffy when they auditioned for Puffy outside Atlanta’s Club 112. Puffy signed them to Bad Boy and changed their name. 112 released their debut single “Only You” in 1996, and it featured verses from Biggie Smalls and a debuting Mase. That song peaked at #13, and the group’s self-titled debut album eventually went double platinum. Another single, the ballad “Cupid,” also peaked at #13.
Puff Daddy didn’t write his “I’ll Be Missing You” lyrics, just as he didn’t write most of his lyrics. (Later, on the 2001 single “Bad Boy For Life,” Puffy almost bragged about that: “Don’t worry if I write rhymes! I write checks!” I don’t know if Puff actually wrote that line, but I’m not worried about it. “Bad Boy For Life” peaked at #33.) At first, Puffy asked Jay-Z, Biggie’s friend and collaborator, to write the “I’ll Be Missing You” lyrics. Jay, who will eventually appear in this column, was already a prolific ghostwriter, but he turned Puffy down and instead suggested his friend, the New York mixtape-rap lifer Sauce Money.
Sauce Money never made a hit on his own. These days, he’s probably better known for his on-again/off-again Jay-Z alliance than for any of his actual music, but that guy could rap. Sauce on Jay’s “Reservoir Dogs,” talking about “hammers fly — might miss you but your man’ll die”? He fucks to win, and y’all are coming to lose? He murders the whole month of April just to take May off and runs with more Germans than Adolf? I’m telling you! Talking to Genius years later, Sauce said that being asked to eulogize Biggie was an “honor.” Sauce also says that he was thinking about his mother, who had died three years earlier, when he wrote Puffy’s “I’ll Be Missing You” lines: “I was kind of talking to my mother… so it was easy for me to jump into that character.”
“I’ll Be Missing You” is structured as Puffy talking to Biggie’s spirit: “Even though you’re gone, we still a team/ Through your family, I’ll fulfill your dream.” Puffy’s delivery is a graceless mutter; he trips all over his lines and finds only the most elementary cadence, like a little kid trying to rap for the first time. In a weird way, that awkwardness may have helped the song’s commercial fortunes. Puff’s verses had none of the linguistic density or rhythmic playfulness of the best rap music. Instead, he was all straightforward and linear, and his words were perfectly distinguishable for people who didn’t ordinarily listen to rap. That’s really just how Puffy rapped, especially back then. The numbness was a feature, not a bug, but it probably also helped Puffy convincingly convey the feeling of being sick with grief. If his rapping was better, then the song might not have hit so big.
Familiarity was also key to the appeal of “I’ll Be Missing You.” In the value system of ’90s rap, it was considered gauche to loop up obvious samples rather than chopping them into idiosyncratic shards. Easy Mo Bee, Biggie’s first producer, has told the story of how he didn’t get the assignment to produce Biggie’s “Juicy” because Puffy wanted someone to take a straightforward loop of Mtume’s “Juicy Fruit” and Mo Bee thought that kind of sampling was wack. The “Every Breath You Take” sample is, if anything, even more obvious. It takes the spectral float of Andy Summers’ guitar and loops it up so that it continues all through the song. On the hook, Faith Evans sings the “Every Breath You Take” hook, changing just enough words to make it about Biggie rather than stalking. (She got a co-writer credit.)
Almost unbelievably, Puffy didn’t clear the “Every Breath You Take” sample before releasing the song. Sting sued, and he reportedly got 100% of the royalties for “I’ll Be Missing You.” Sting’s police bandmate Andy Summers, who came up with the riff that runs all through “I’ll Be Missing You,” didn’t have a writing credit on “Every Breath You Take,” so he didn’t get one on “I’ll Be Missing You,” either. Summers has complained bitterly about “I’ll Be Missing You” and about hearing his own riff constantly for that whole summer, but it’s not Puffy’s fault that Andy Summers didn’t have his paperwork right. There was no bad blood between Sting and Puff Daddy. At the VMAs in September ’97, after “I’ll Be Missing You” had been ruling the earth for months, Sting performed the track with Puffy and a gospel choir.
With “I’ll Be Missing You,” Puffy essentially appointed himself Biggie’s chief mourner. He wore that role awkwardly. Puffy is an egomaniac; that’s his superpower. (I sometimes wonder how fellow egomaniac Clive Davis, whose label Arista partnered with Puffy to launch Bad Boy, felt when he watched Puffy go from record exec to artist. Maybe Clive Davis wished that he would’ve jumped on a Janis Joplin record in 1970.) With “I’ll Be Missing You,” Puffy was at least ostensibly trying to move the focus off of himself and onto his dead friend, but it didn’t play that way. Maybe that’s not a problem. Puffy has always thought of himself as an entertainer, and maybe he just couldn’t do solemn. Maybe “I’ll Be Missing You” stuck around the way that it did because it’s a little too energetic to be fully maudlin.
For the “I’ll Be Missing You” video, Puffy worked with Hype Williams, the greatest music-video director who has ever lived. The images are almost narcotic in their impact — the verdant green hills, the golden-hour sunlight, the orange glow of rain hitting lit-up pavement. They shot the video in Chicago, a place where I used to live, and I can report that I get an overpowering urge to dance like Puffy every time I’m in those lit-up moving walkways under O’Hare, one of the clip’s locations. The video plays less as a tribute and more as Puffy’s monument to himself — the motorcycle crash, the dancing in the rain, all of it.
“I’ll Be Missing You” was the first rap song ever to debut at #1, and Puffy released his debut album, which he’d retitled No Way Out, during the long stretch of time that “I’ll Be Missing You” sat atop the Hot 100. On the album track “Pain,” Puffy imagines a visit from Biggie’s ghost: “He puts his hands on my head and said ‘I live through you/ Make hits continuous, this is what we do.'” From that perspective, then, Puffy really was honoring Biggie’s memory even while moving the focus to himself. It’s a neat rhetorical trick. He’s capitalizing on his friend’s murder because he knows that’s what his friend would’ve wanted.
I believe him. Biggie probably really would’ve wanted Puffy to shine in his absence. Songs like “I’ll Be Missing You” have probably helped burnish Biggie’s legacy, and they’re probably part of the reason why Biggie is remembered as maybe the greatest rapper of all time, though the actual music that Biggie made obviously has more to do with that. Nothing comparable ever happened with Biggie’s friend-turned-foe Tupac Shakur. By the time Pac died, most of the other big Death Row stars had already left the label. Death Row kept cranking out posthumous Pac albums, but the label didn’t have anyone with enough charisma or gravity to release a resonant Pac tribute. Bad Boy, by contrast, had its shit together.
But “I’ll Be Missing You” hit so big that it eventually transcended its origins. Plenty of the people who enjoyed the song probably didn’t know anything about Biggie in the first place. At some point, the song came to transcend death itself. Years later, when my little sister graduated from middle school, “I’ll Be Missing You” soundtracked a slideshow of memories. Those kids hadn’t died. Most of them were even going to the same high school. But maybe some of them would be missing others, and I guess that was enough for the song to fit. When the played the slideshow in the auditorium, the kids yelled for the adults to turn it up. Maybe that same line of thinking is why Puffy got booked to perform “I’ll Be Missing You” at a Princess Diana memorial in 2007, even though the song definitely isn’t about Princess Di.
Biggie’s death ended the central tension — the balance of Biggie’s rap artistry with Puffy’s pop instincts — that made Bad Boy’s best records work. Without Biggie, Bad Boy became all pop, all the time. Puffy really did make hits continuous. In the summer of 1997, the “I’ll Be Missing You” single went triple platinum before No Way Out had even arrived in stores. No Way Out went platinum seven times over, selling more copies than even Biggie’s posthumous album Life After Death, which Puff awkwardly plugged during the lyrics of “I’ll Be Missing You.” (Life After Death went diamond, but it’s a double CD, so each sale counts twice.)
Bad Boy ruled the Hot 100 for all of 1997, and No Way Out spun off more hits. Puff followed “I’ll Be Missing You” with a maxi-single that featured the swaggering club monster “It’s All About The Benjamins (Remix),” which started off as a Puffy/Lox collab on a 1996 DJ Clue mixtape. With added verses from Lil Kim and Biggie — and then with a rock remix that also featured people like Rob Zombie and Dave Grohl — “Benjamins” became inescapable. It might not have been a #1 hit, but “Benjamins” is still the song that I associate the most with the whole Bad Boy era.
The other song on the “Benjamins” maxi-single — the one that actually officially charted — was the Mase/Biggie collab “Been Around The World,” which took the beat from David Bowie’s “Let’s Dance” and the hook from Lisa Stansfield’s “All Around The World.” For the video, Puffy wrote and produced an absurd 10-minute action-movie epic that was full of celebrity cameos. One of those cameos was the movie star Jennifer Lopez, who soon became Puffy’s girlfriend and who will appear in this column a bunch of times. “Been Around The World” peaked at #2. (It’s a 5.)
On the No Way Out album track “Don’t Stop What You’re Doing,” Puffy bragged, “Every single I drop, two or better.” For a while, that was true. The first three singles from No Way Out all made it to #1 or #2. Puffy finally broke the streak with “Victory,” which only made it to #19 even though it’s awesome. “Victory” is Puffy, Biggie, and Busta Rhymes rapping over Bill Conti’s score from Rocky, and it sounds like suns exploding. I wish Puffy had gone for more of that kind of over-the-top epicness, though I can’t stand the way that the extremely expensive music video goes all-in on explosion sound effects and makes the song itself practically unlistenable.
Faith Evans and 112 didn’t continue to dominate charts after “I’ll Be Missing You” the way that Puffy did. In 1998, Faith made it to #7 with her single “Love Like This,” and she also guested on Whitney Houston’s #2 hit “Heartbreak Hotel.” (They’re both 8s.) 112 released two more platinum albums on Bad Boy, and they made it to #4 with their sticky, streamlined 2001 club track “Peaches & Cream.” (It’s a 9.)
In the early ’00s, both Faith and 112 parted ways with Bad Boy, though they’ve both returned to the fold for various reunion-show packages and special awards-show performances. Faith Evans did a little acting, published a memoir, and released an album of posthumous Biggie collaborations. She divorced Todd Russaw in 2011 and married “I’ll Be Missing You” co-producer Stevie J in 2018. Last year, Faith was arrested and charged with committing felony domestic violence against Stevie. Those charges were dropped, and the couple divorced. That same year, Faith went on The Masked Singer.
Faith Evans and 112 probably won’t appear in this column again, but Puff Daddy will, and he’ll show up soon. Bad Boy Records’ dominant run wasn’t over yet.
GRADE: 4/10
BONUS BEATS: Here’s Jackie Chan emotionally car-dancing to “I’ll Be Missing You” in the 2001 film Rush Hour 2:
BONUS BONUS BEATS: Here’s the dancehall version of “I’ll Be Missing You” that Beenie Man released in 2005:
(Beenie Man’s highest-charting single, the 2004 Ms. Thing/Shawwna collab “Dude,” peaked at #26.)
BONUS BONUS BONUS BEATS: Here’s BTS covering “I’ll Be Missing You” for the BBC Live Lounge in 2021:
(BTS will appear in this column a bunch of times.)
THE ASTERISK: This seems utterly absurd, but Will Smith’s gargantuan movie theme “Men In Black” was never released as a single, so it never charted on the Hot 100. But “Men In Black” still had a long run atop the Billboard Radio Songs chart, starting during the reign of “I’ll Be Missing You.” “Men In Black” almost certainly would’ve been a #1 hit if it had been able to compete. It’s a 5.
New Zealand one-hit wonder OMC got to #4 on the Radio Songs chart with the daffy, dazed post-Beck jam “How Bizarre” while “I’ll Be Missing You” sat at #1. Like “Men In Black,” “How Bizarre” never came out as a single in the US. It probably wouldn’t have made it to #1 even with a single release, but I guess we’ll never know. It’s a 9.
