June 14, 1997 was a new day for rap.
Fans still were mourning the unsolved March 9 murder of 24-year-old star The Notorious B.I.G. in Hollywood as the one-year anniversary of Tupac Shakur's killing approached. Both were icons, helping bridge the gap between hip-hop and pop. But Sean "Diddy" Combs (then-known as Puff Daddy) — the 27-year-old head of B.I.G.'s label home, Bad Boy, and a rising rapper himself — had bigger plans. On June 14, his single "I'll Be Missing You," a tribute to B.I.G., made its Billboard Hot 100 debut at No. 1, a feat then only achieved four times before, and stayed there for 11 weeks. The song went on to become the second-best-selling single of the year, according to Nielsen SoundScan, and helped Combs' debut, "No Way Out," sell 3.4 million copies.
"All this chart news must still be bittersweet to Combs," Billboard wrote at the time. "[He] isn't just the head of the label that signed B.I.G.; he also counted the artist as one of his best friends."
"I'll Be Missing You" mourned the passing of a superstar, but also helped usher in a new one, and the new day he represented: the so-called shiny suit era, named after Combs' frequent choice of attire. Video budgets ballooned, as did rappers' pop ambitions, and Combs was leading the way.
He was no wordsmith like his slain friend, but "I'll Be Missing You" proved Combs knew the recipe for a hit. It heavily sampled The Police's 1983 "Every Breath You Take" — also a Hot 100 No. 1 (for eight weeks) — and featured Bad Boy act 112 and Biggie's widow, Faith Evans. During his career, Combs perfected the formula: He has landed 15 top 10s on the Hot 100, including five No. 1s.