Jay-Z Admitted He Went Into 'A**hole Mode' When He Tried to Connect With a Hip-Hop Mogul
Jay-Z met a powerful hip-hop mogul long before he was famous. He shared why he became angry with someone who could have helped his career.
Music
Jay-Z competed in a rap contest when he was a teenager. It could have altered the course of his life, but he got frustrated with a hip-hop mogul.
by Emma McKee
Published on January 18, 2025
In the earliest stages of Jay-Z’s music career, he connected with hip-hop mogul Russell Simmons. Simmons found his performance at a talent show impressive and requested that Jay-Z give him a call. When his attempt to reach out to Simmons failed, Jay-Z said he snapped.
When Jay-Z was a teenager, he entered a talent contest in Queens. He wasn’t entirely sure what he was getting into, but he agreed to go.
“The first time I met Russell Simmons was at a rap talent contest out in Queens,” he told Vibe Magazine. “Somebody, it had to have been my cousin B-Hi, entered me and didn’t tell me where it was. There’s no way they would’ve gotten me to go to Queens without doing it like that. LL. Cool J was one of the judges. I was crazy young, like 15. I remember I had a gun on me, the same one I used to carry around in an empty VHS box.”
Russell Simmons | Matt Winkelmeyer/Getty Images for The Recording AcademyWhile he didn’t win, he impressed Simmons.
“I lost,” he said. “I got second place, which to me, then and now, was the same as coming in 50th. But Russell came down from the stage and was like, ‘Yo, kid, I want you to call me, here’s my number.’”
Jay-Z tried to call Simmons, but when he couldn’t connect with him immediately, he got frustrated.
“I tried to call him one day, and they told me he wasn’t there,” he said, adding, “I might’ve tried calling one other time, but after that I went into a**hole mode, like, I ain’t calling this [n-word] again, you crazy! I never told him that story.”
Years after the fact, in 1997, Jay-Z reached a distribution deal with Def Jam, Simmons’ company. He didn’t remind Simmons that they’d met before.
“Years later, Damon Dash and I had a million-dollar deal on the table with Def Jam,” he said. “I still have that a**hole in me, like, If he doesn’t remember, I’m not reminding him. Things happen when they’re supposed to, what they say about divine time is basically true.”
Simmons is currently living in Bali after a number of women accused him of sexual harassment, assault, and rape. His accusers began coming forward in 2017.
In 2020, Jay-Z’s streaming service TIDAL hosted Simmons on the podcast Drink Champs. Many, including activist and writer Sil Lai Abrams, called out Jay-Z for platforming Simmons.
“This is the second time in as many weeks that Russell Simmons has been given the space to speak out about issues around social justice on media platforms owned entirely or in large part by other Black media moguls,” she told The Daily Beast. “So Jay-Z, who positions himself as a staunch supporter of social justice, has allowed this to take place.”
Russell Simmons and Jay-Z | Frank Micelotta/Getty ImagesShe found it appalling that influential figures like Jay-Z and Sean “Diddy” Combs weren’t critical of Simmons.
“What we see with these media moguls is a replication of the oppression that they experience as Black men but they’re doing it to Black women. They’re using intimidation tactics by giving a serial predator like Russell Simmons a place online to terrorize his survivors,” she said. “It also speaks to how interwoven all of the relationships within music — and in this case I’m speaking specifically about hip-hop — truly are. Because it cannot be a coincidence that two of the most prominent moguls in the industry [Jay-Z and Diddy] are quietly sliding Russell in on these discussions.”
How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area.
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