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Sean “Diddy” Combs founded Bad Boy Records in early 1990s and went on to sign major artists including The Notorious B.I.G., Foxy Brown, and Faith Evans. But when Diddy had the opportunity to sign future G-Unit rapper 50 Cent, Diddy decided to pass on signing the up-and-coming emcee.

Sean "Diddy" Combs, founder of Bad Boy Records, didn't sign 50 Cent to his label
Sean “Diddy” Combs | Paras Griffin/Getty Images

Diddy passed on signing 50 Cent

50 Cent‘s fellow G-Unit rapper Tony Yayo spoke about 50’s experience with Diddy back in the day in a 2022 interview on VladTV. He and 50 scheduled a meeting with the Bad Boy Records executive about a potential record deal, but the meeting didn’t exactly go as planned.

“A lot of people don’t know this story,” he said. “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. I know that was one of the biggest mistakes of Bad Boy. And you know, the [Kenneth “Supreme” McGriff] situation — a lot of people were scared of Preme — 50 wasn’t.” McGriff was a convicted drug lord who was accused of being connected to a plot to kill 50 Cent.

“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.’”

He passed on signing 50 Cent

The meeting took place after 50 Cent released his 1999 debut single “How to Rob”; on the track, he rapped about extorting Diddy, along with other veiled threats against prominent rappers. The following May, 50 was shot nine times. Following the shooting, Diddy was apparently wary of signing another artist associated with guns and gun violence after the death of his friend, The Notorious B.I.G.

“We had a meeting with Diddy, it was me and 50, and he took the meeting out of respect,” he remembered. “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**** on the planet.

“This was after ‘How to Rob,’ just after he got shot and he had all the mixtapes s*** on smash,” he said, noting that 50 Cent had written songs for Diddy in the past.

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Diddy gave 50 Cent and Tony Yayo advice on lyrics

50 and Tony got a word of advice from Diddy during that meeting that stuck with him afterward.

“Out that meeting, [Diddy] said, ‘Three things about rappers: bank accounts, b****es and Bentleys,'” he said. “We didn’t have any money at that point, but it stayed in my head.”

“And later on, I had what he said,” he concluded. “I had bank accounts, bitches and Bentleys. And that makes you a target. I’ve been shot at numerous times, but I say those prayers before I leave the house.”