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In 1994, the late rapper Notorious B.I.G. released a single titled “Just Playing (Dreams)” off his debut album Ready to Die. In the lyrics, Biggie lists his favorite R&B singers and romances them in his dreams.

He targeted R&B group Xscape with a vicious jab, saying, “I’ll f–k RuPaul before I f–k them ugly-ass Xscape bitches.”

He also made a questionable remark about 8-year-old Raven-Symoné: “make Raven-Symoné call date rape.”

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While RuPaul and Raven-Symoné weren’t offended by the lyrics, Xscape took offense to Biggie calling them “ugly”.

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At the time, Xscape was still riding high off their 1993 debut album, Hummin’ Comin’ at ‘Cha. The album spawned the hit singles “Just Kickin’ It”, “Understanding”, “Love on My Mind” and “Tonight”.

Hummin’ Comin’ at ‘Cha peaked at No. 17 on the Billboard Hot 200 chart.

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In nearly every interview they gave in 1994, Xscape mentioned Biggie’s lyrics and that they were offended and hurt by what he said.

Their producer, Jermaine Dupri reportedly made Biggie apologize to his group.

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In an interview on “The Morning Hustle” podcast, Xscape lead singer Tameka “Tiny” Harris (right) recalls Biggie apologized to them before he was fatally shot in Los Angeles in 1997 at age 24.

“Somebody came… I don’t know if it was Diddy… somebody came and said Biggie wanna speak to y’all,” said Tiny. “I was just like, ‘I’m going to see what he’s talking about.’ And you know, he was very nice, he was very apologetic and he basically said, ‘I don’t know what I was thinking. Look, I’m ugly. I’m ugly as hell. Y’all is beautiful, and I just wanted to say I apologize.'”

Tiny said the apology came just minutes before he was killed in a drive-by shooting following an afterparty on March 9, 1997.

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Biggie (pictured with Sean Combs in 1995) is considered one of the greatest rappers of all time. But he was very self-conscious about his looks and he may have projected his insecurities on the 4 members of Xscape.

In his 1995 hit single “One More Chance,” Biggie rapped: “Black and ugly as ever, however I stay Gucci down to the socks, rings and watch filled with Rocks.”

Watch the interview below.

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