Shyne Reflects on Dating Brandy During Ma$e Relationship and Diddy’s Disapproval

Moses Michael Levi “Shyne” Barrow continues to open up about his time at Bad Boy Records, sharing candid moments about his former boss Sean “Diddy” Combs and his labelmates. As the Belizean politician promotes his Hulu documentary, The Honorable Shyne, new revelations have surfaced about his relationships during his early rap career.

In the documentary, the late DJ Clark Kent claims that Shyne began dating R&B star Brandy while she was involved with Ma$e, her collaborator on the hit “Sittin’ On Top Of The World.” During a recent Breakfast Club interview, Shyne recalled how his relationship with Brandy caused tension with Diddy and within the Bad Boy family.

“At the time, I got on in ’98, and instead of getting in the studio and getting the information, I was living the life,” Shyne admitted. “That caused a strain between him [Diddy] and I, because he’s like, ‘who does this kid think he is?’”

Shyne explained that his pursuit of Brandy led to a “family meeting” to address the situation.

“Ma$e was dating a girl, and I started dating the girl, and that caused a big thing,” he shared. “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!’”

The former rapper admitted that his arrogance continued until Brandy herself gave him a reality check the following year.

“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,’” Shyne recalled.

“That hit me like the hand of God, because she was right.”

Shyne’s latest revelations come as he continues to reflect on his journey in music and politics. Watch the clip from The Breakfast Club and check out the full interview for more insights into Shyne’s life.