The Notorious B.I.G.’s only album released while he was still alive, ‘Ready to Die,’ celebrated its 21st anniversary on September 13. In our latest #HSTBT, we explore “what could have been” if Diddy had never left Uptown and formed Bad Boy Records.

It’s hard to believe that The Notorious B.I.G. only released one album while he was still alive. Even after 21 years, Ready to Die continues to be one of the most important rap records of all-time – not only giving the world one of the G.O.A.T.’s, but also infusing a street narrative into a genre which in the past had seen some of its most popular releases rely on more PG themes.

While his career will always be intertwined with Diddy’s notable rise from A&R to music mogul, there’s no denying that Smalls’ career would have been decidedly different had he and Puffy followed Uptown Records’ original vision of what kind of music he should be making.

In 1990, Diddy was working at Uptown Records as an intern following a two-year stint attending Howard University where he majored in business and found himself earning a reputation as a connector by producing weekly dance parties and running an airport shuttle service while attending classes.

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Andre Harrell was the CEO and founder of Uptown Records. He would quickly see value in Combs’ work ethic and vision. “Puff had just started as an intern and I gave him a tape to take to Unique Studios, about 10 blocks away,” Harrell told Billboard. “By the time I finished the phone call I was on, he came back — his tie was sideways and behind his back — and I asked, ‘How did you get there so fast?’ He said, ‘I ran there and I ran back.’ And I thought to myself, ‘Oh, this kid is going to be a problem right here. He’s eager to go.’ And I don’t mean a bad problem — a force to be reckoned with.”

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In March 1992, Christopher Wallace was 20 years old and received his first big break as an emcee when he was featured in The Source‍‍ ’​‍s Unsigned Hype column based off the strength of a three-song demo recorded under the moniker, “Biggie Smalls” which was created in DJ 50 Grand’s Bedford Avenue basement. The demo soon found its way into the hands of Diddy who signed him to Uptown Records.

Wallace’s first major appearance was on Heavy D & The Boyz’s “A Bunch of Niggas” from their 1993 album, Blue Funk. Soon after, the duo of Biggie and Combs went to work on his debut album – recording songs like “Ready To Die,” “Gimme The Loot” and “Things Done Changed” that same year.

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While no one at Uptown Records could deny that Combs was an asset to the company, his reputation and ego were starting to irk his co-workers.

“Andre cultivated Puffy. And Puff was a genius,” Russell Simmons told New York Magazine. “But Puffy also seemed like a trouble magnet. He was getting into fistfights constantly, constantly. He was a young kid; he needed management. Andre would be like, ‘Yo, Puff, you can’t beat up people and do this and do that!’ Andre stood by Puffy through a lot of shit.”

With less than half of Biggie’s album recorded, Combs was summoned to Andre Harrell’s office. The CEO knew he had one of two choices: he could either force them to change the creative direction of the album after executives at MCA had heard the preliminary songs and didn’t like them. Or, he could do something which on paper was much harsher – albeit better.

“When I fired him, it was like I had an artist in the building,” Harrell told The Wall Street Journal. “‘Cause Puff as an executive – he was a really artistic guy – he can make videos, he could style. I started to branch out into movies and television. So then Puff wouldn’t really listen to anybody but me. So my full-time job became managing Puff. And I was doing other things. Even when I let Puff go, he was always on payroll.  I never stopped paying him until he found his next spot. His artists were still getting per diem. Because I didn’t do it to hurt him, but I knew it was time for him to grow. And the only way he was going to grow was he was going to have to have the same kind of corporate conversations that I was subjected to. And then he would understand what he could and could not do.”

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“Whereas I had Heavy D – who was more like a happy, female-loving, uplifting, celebratory artist – Puff’s ‘Heavy D’ was Biggie Smalls,” Harrell says. “Biggie Smalls was more in the streets – telling street stories. Biggie Smalls ended up becoming my favorite rapper of all time. I told Puff, ‘you need to go and create your own opportunities. You [sic] red hot. I’m really letting you go so you can get rich.'”

When Combs departed Uptown to form Bad Boy Records, Harrell allowed him to take Biggie with him despite his contract with the label.

Ready to Die was released September 13, 1994. It was certified gold two months after its release on November 16, 1994, and was certified double platinum on October 16, 1995 – only a year and one month after its release.

Words by Alec Banks
Features Editor

Alec Banks is a Los Angeles-based long-form writer with over a decade of experience covering fashion, music, sports, and culture.