On February 11, 1990 Mike Tyson fought Buster Douglas at The Tokyo Dome. In 10 rounds, the fight would go down in history as one of boxing’s biggest upsets. The undefeated, undisputed heavyweight champion lost to Douglas, an underdog with four losses and a draw to his name at the time. The fight billed as “Tyson Is Back!” showed many fans the opposite, as one of the greatest athletes in all of sports history showed that he could be beaten, and by an unlikely opponent.

On the latest episode of Questlove Supreme (available on Pandora), Bobby Brown tells an amazing story that adds some interesting background to the events surrounding February 10 and February 11, 1990. The New Edition co-founder details what may be the real reason one of boxing’s greatest, most physical fighters caught his first L.

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The R&B/Pop superstar was in between the massive success of 1988’s Don’t Be Cruel and 1992’s Bobby. He was in Japan during his Dance Ya’ Know It Japan Tour, and able to kick it with his friend “Iron” Mike (and for those that listen, Bob does a pretty damn good Tyson impression).

“[Mike Tyson and I were] in Japan. We hooked up [there],” Bobby tells Questlove, Phonte, Laiya, Suga Steve, and Unpaid Bill near the end of their interview. “We basically stayed up all night partying with maybe 12 Japanese girls and just me and Mike. It was just the funniest night, ever. We had a ball, but it was just the funniest night ever. I kept tellin’ him, I kept tellin’ him, and I kept tellin’ him…I was like, ‘Mike, you need to go get some sleep; you got a fight tomorrow.’ He’s like [mimicking Mike Tyson] ‘Bobby. Listen. Buster Douglas, listen—he’s an amateur! I could beat him if I didn’t sleep for five weeks. Watch how quick this fight ends; this is gonna be one of my quickest fights.’ I was like, ‘Mike? Alright.’ He was like, ‘Don’t worry, man; you worry so much.”

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“Lo and behold, I had to go to Osaka and I couldn’t go to the fight,” recalls Brown of his time in Japan. “I’m sittin’ there at this emperor’s place and he has [the fight] on his big screen. We’re watchin’ it. I’m looking at Mike and I’m seeing the fatigue in him. I was just like, ‘Aw sh*t.’ Then them punches came—boom, boom, pow, boom, BOOM, and I just started cryin’ like a baby. I cried so bad. I cried so bad!”

Brown explains the pain he felt. “That hurt. It hurt me to my core. I couldn’t breathe. And I had to go on stage. So I was just [out of breath]. I think that’s when I started having panic attacks. I was like, ‘Oh my God, he’s gonna kill me. He’s gonna kill me. He’s just gonna destroy me when he sees me.’ Then I started thinkin’ about it, I kept tellin’ [guy] to go bed. Why would he be mad at me?”

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The cast of interviewers ask what happened next. Bobby explains, “After the fight he called me on the phone. He said, ‘Bob, you was right. You was so right. I was so sleepy there; my legs were mush in there. That’s why Cus D’Amato told me don’t have sex before a fight.’ I was like, ‘Yeah, and you had a lot of sex too! A lotta sex; it wasn’t just one person. You had a lot of sex!”

Bobby Brown also addresses the story in his 2017 memoir, Every Little Step: My Story. In the QLS conversation, Brown explains why he credits himself as New Edition’s founder and recalls LL Cool J getting his chain snatched at New York City’s Latin Quarter nightclub.

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Notably, Bobby Brown recently reunited with Babyface and Teddy Riley for his single, “Like Bobby.” The song actually serves as an homage to a Questlove creation, The Roots’ “The Next Movement.”