When did Shyne date Brandy? Former rapper says Diddy disapproved of the singer’s simultaneous romance with Ma$e at the time

Celebrities Visit SiriusXM - November 14, 2024 - Source: Getty
Shyne visits SiriusXM Studios in New York City, November 14, 2024. (Image via Getty/Roy Rochlin)

Rapper-turned-politician Shyne sat down for an interview with The Breakfast Club to spill the tea on his past romances, and Diddy's butting in. He divulged that in the past, when he was dating Brandy and Ma$e simultaneously, Diddy confronted him.

Shyne, whose real name is Moses Michael Levi Barrow, started a romance with R&B singer Brandy in 1998. At the time, she was also seeing her Sittin’ On Top Of The World collaborator, Ma$e, and thus, the three began a love triangle.

At the 24-minute mark of the video, he divulged that he felt powerful when he was signed to Bad Boy Records:

"I thought I was Puff. There's stories of his, like, main girl that, you know, I was dealing with because I thought I was that guy."

Shyne admits he had to have a "family meeting" with Diddy, and notes that Brandy once had to humble him

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When Charlamagne, one of the hosts, asked Shyne if he was in a relationship with Jennifer Lopez, he asserted that it wasn't her.

"I can't say who, but not her. I got in in '98, and instead of getting in the studio and getting the information, I was living the life and so that caused a strain between [Diddy] and I. He was like, 'Who does this kid think he is?' And there's even situations like with Mase. Mase was dating a girl and I started dating the girl and that caused a big thing."

He went on to reveal that he had to have a sit-down with Puff:

"We had to have a family meeting, like, ‘Yo, what are you doing? You’re like Kobe coming to the Lakers and you want to go after Shaq’s joint, you can’t do that!'”

He also added that ego got the better of him for a long time until one fine day when Brandy decided to humble him:

"The girl that’s also seeing Ma$e, she’s selling millions of records, she had the biggest record that year…we had an argument and she said, ‘yo, you’re nobody. You ain’t sell one record. You think you stylin’, you think you’re that, you’re nothing. You haven’t sold a record,’ and that hit me like the hand of God, because she was right.”

In another part of the interview, Shyne also recounted an instance of Diddy paying a visit to him in prison in 1999. He revealed that he was simply taken to the lawyer's office, unaware of what was going on, only to find Puff waiting for him. He also admitted that he "tried to spit in his face."

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Edited by Abhimanyu Sharma