Bad Boy was one of Diddy’s most profitable ventures. Founded as an imprint of Sony Music Group, Bad Boy Entertainment was set up so that Diddy, who had his ear to the streets of the East Coast, could draft in the best new talent hip hop had to offer.
Following the death of Biggie Smalls in 1997, the label was on the look for a new star and at the turn of the millennium Diddy (real name Sean Combs) was presented with 50 Cent. However, the mogul refused to sign the ‘In Da Club’ emcee.
In a 2022 appearance on VladTV, former G-Unit member Tony Yayo detailed 50 Cent’s scheduled meeting with the Bad Boy executive about a potential record deal. However, it didn’t work out. Recalling the story, Yayo stated, “A lot of people don’t know this story. 50 went to Diddy for Bad Boy. A lot of people don’t know that. We had the meeting. And it was so crazy that Diddy didn’t sign him.”
He continued, “I remember Diddy said this, he don’t even remember. He said, ‘The three things people hate about rappers.’ He was like, ‘Yeah, we can’t sign you, playboy. It’s too much. It’s too much drama with the Biggie stuff and all that.’” The meeting was scheduled following the success of 50 Cent’s 1999 single ‘How to Rob.’ However, Combs was nervous about signing an artist associated with guns and a gangster image following the death of Biggie Smalls.
Yayo continued to recall the meeting, divulging, “We had a meeting with Diddy, it was me and 50, and he took the meeting out of respect. He had deals all over the table. I wasn’t saying he was gonna take the deal, he might have not. But Diddy didn’t wanna take the deal ’cause of all the drama, but 50 was the hottest n*gga on the planet.”
Yayo explained how during this period, 50 was on a mixtape run, and everybody in New York knew he was going to be the next big thing. However, everyone was hesitant to sign him due to his street affiliations.
However, following the release of his debut mixtape Guess Who’s Back? Eminem took the leap of faith with the Queens rapper, and shortly after its release, he signed to Eminem’s Shady Records under Interscope and began work on his debut album, Get Rich Or Die Tryin’, which is widely considered legendary.