Jay Z on the cover of Vanity Fair's November 2013 issue (Mario Testino/VanityFair.com)
Jay Z on the cover of Vanity Fair's November 2013 issue (Mario Testino/VanityFair.com)

The first time Jay Z appeared on the cover of Vanity Fair, in 2001, life was remarkably different for the rap icon and businessman, who graces the cover of the glossy's November issue. For one, there is the difference in wardrobe choices. Back then he wore a Yankees jersey, jeans (presumably from his clothing line, Rocawear) and a scowl on his face. In 2013 he's wearing a white tuxedo jacket (presumably Tom Ford), bow tie and black pants, and the look on his face, although not quite a smile, is definitely not a mean mug, either.

Another noticeable difference: His last appearance on a Vanity Fair cover was as part of a collective of artists for the music issue. He stood alongside greats like David Bowie, Stevie Wonder, Missy Elliott and Beyoncé. This time Jay Z appears by himself, the face of the magazine's 2013 New Establishment issue, with the title "the New Chairman of the Board" and as the subject of a profile by Lisa Robinson, in which he is being asked what it was like courting his former fellow cover subject, whom he now calls his wife.

Jay says that when he and Beyoncé were both featured on the cover of Vanity Fair's 2001 Music Issue "we were just beginning to try to date each other." Try? "Well, you know, you've got to try first. You got to dazzle … wine and dine." He tells Robinson that "of course" he pursued Beyoncé, and when asked if he hadn't been Jay Z — say, he had been a gas-station attendant and she pulled up — would he have been able to date her, he responds, "If I'm as cool as I am, yes. But she's a charming Southern girl, you know, she's not impressed … But I would have definitely had to be this cool." Jay confirms that the line on his latest album, "She was a good girl 'til she knew me" is about Beyoncé, and when Robinson asks if she's not a good girl anymore, Jay laughs, saying, "Nah. She's gangsta now."


Whether or not you choose to believe that Jay Z could have nabbed Beyoncé if he were simply a gas station clerk named Shawn Carter, one thing is for certain: He would have never been on the cover of Vanity Fair discussing his various business ventures outside of music. 

Though he professes he still has a love for rap — "That's how I know I love it. Thirty years old was my cutoff, but I'm still here, 43 years old" — the focus of the article is on life as a businessman. He talks about how his past as a drug dealer could be an asset to his new career as a sports agent, in charge of Roc Nation Sports.

"I know about budgets. I was a drug dealer," he tells Robinson. "To be in a drug deal, you need to know what you can spend, what you need to re-up. Or if you want to start some sort of barbershop or car wash — those were the businesses back then. Things you can get in easily to get out of [that] life. At some point, you have to have an exit strategy, because your window is very small; you're going to get locked up or you're going to die."

Jay Z was also on the cover of Vanity Fair in 2007, with actor George Clooney, for the magazine's Africa issue. 

Read more at Vanity Fair.

Jozen Cummings is the author and creator of the popular relationship blog Until I Get Married, which is currently in development for a television series with Warner Bros. He also hosts a weekly podcast with WNYC about Empire called Empire Afterparty, is a contributor at VerySmartBrothas.com and works at Twitter as an editorial curator. Follow him on Twitter.

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