That Time I Hung Out With Jay-Z

It all started at Yankee Stadium, when I sat next to Jay-Z and his close friend Juan; better known as "OG".

Jay and I are both Brooklyn guys, so I've been lucky to cross paths with him a few times over the years. I went to his 40/40 Club once, and have seen him at the stadium from time to time.

At the game that day, he asked me if I ever wanted to go to one of his concerts. I took advantage of the situation and responded "Concert? No, I need to be backstage with you! I need to fly with you!"

Truth is, I didn't know much about rap and hip hop. I honestly felt a little uncomfortable about what it was and what it represented, but I'll admit that I never gave it a fair shot prior.

So, he invited me to go backstage to one of his shows on his "Home & Home Tour" with Eminem. I was interested in going for sure, but I was nervous that I wasn't going to appreciate it as much as most others in this day in age would.

I was giving a speech in Connecticut earlier that day as part of my "You Gotta Have Balls" book tour (had to get in one shameless book plug here). After the speech, I started heading to Yankee Stadium... until I decided to get off at the next exit and head home. I couldn't do it.

But then "Little Brandon" came to my rescue. "Little Brandon" is what I call the voice inside my head. He said "Brandon, you just wrote a book called 'You Gotta Have Balls' and you don't have balls right now!" Needless to say, LB stripped me of my voting rights that day and forced me to go to the show.

I met OG at the stadium, and he took me backstage and showed me where the green room was. I asked him if that was where the celebrities would be. "I think there will be, but we're not going there. Jay has his own private room," OG answered.

Sure enough, I ended up in a private room with Jay-Z, OG, and another one of his friends. Out of nowhere, he started DJ'ing for us.

Since I was unfamiliar with the genre and its surrounding culture, I asked him why this show was important to him. He seemed amped up.

His answer really moved me. "Bro, it's Yankee Stadium! I know I've played a lot of venues, but I'm more interested in significance than success. When I play at Yankee Stadium it's different. The people who show up will be the most diverse. I want my music to be attractive to all races and cultures."

I met all kinds of celebrities that night. I watched both Eminem's set and Jay-Z's set with P. Diddy (which is a story for another night)! I even saw Beyonce up close!

That night, I learned what Jay-Z was all about. He plays the long game, and is interested in collecting as many thoughts and opinions from as widespread an audience as he could attain. Hell, this explains why he invited a 50-something year old guy like me!

Often times, we choose who we spend time with, and most people prefer to be with similar people who share similar views and have common interests. This was not Jay. He was okay hanging out with me, and I was certainly okay hanging out with him!

I also learned so much about an art form that has become so incredibly popular. I thought hip hop was tailored primarily to urban kids, and didn't realize how diverse an audience it gathered. I'm glad I gave it a chance.

In total, I spent 3 hours with Jay-Z before the show, and we talked about everything. Later on, he looked at me and asks "you good? You having fun?" I couldn't believe he actually gave a shit.

You may be questioning whether this actually happened at this point. I said "Jay, I don't think anyone is going to believe that we hung out." "Let's take some photos," he said. It was so dark where we were, so we took like 10 pictures so I made sure I could capture what was truly an unforgettable night.

"Listen, you good? Anything else?" he asked. "I would like to get that jacket you've got on," I said. He said no. He did offer for me to join him at his next destination in the city, but this time I turned him down. I would've probably gotten home at 10:00 am the next morning most likely, which isn't a good way to stay married.

The moral of this story, you ask? It's simple: you gotta have balls. I didn't know any better about hip hop because I never gave it a chance.

Song of the Day: "Empire State of Mind" by Jay-Z featuring Alicia Keys

Quote of the Day: "I'm not a business-man, I'm a business, man!" - Jay-Z


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  • Cool story bro! Although that phrase can be taken as sarcasm nowadays, I mean it! I have the balls that everyone wishes they did. I would’ve went with Jay Z to the next destination because I have nobody at home to answer to and I prefer to keep it that way, for the time being :) By the way, very nice website and brand you have created. I have been following sports my entire life and have always been aware of Steinier Sports! So, next time I am in New York, can I get the private tour and go to a ballgame with you?


  • Brandon,

    As a huge Jay fan on and off the mic, I must say this was a very cool story!
    To me, Jay is an icon, a role model,and extremely intelligent person.

    I had the opportunity in meeting him once in Fort Lee NJ in the Summer of 2002. They say music Mark’s time, so to give you some context of this story I’ll share with you a week earlier to meeting him, I watched him perform at Hot 97’s Summer Jam. Already the largest pop/hip hop act in the industry with a collaboration song at the time with the king of pop himself, MJ. During his performance he stopped to bring out MJ and the whole crowd went absolutely nuts.

    Fast forward one week later, I’m on my lunch break from work, I was life guarding that summer at a near by pool. I was leaving the burger king I would usually eat at, and I see a black Mercedes CL 600, white with glistening chrome rims pull up at the gas station across the street. A tall man wearing a long white t shirt hops out, wearing a brand new pair of my favorite sneakers at the time, Nike air force ones, whiter then the clouds that hover the sky in Aruba. It was Jay-Z, Hova, Jigga man, Mr S.Carter himself. I walked over and approached him, he shook my hand and said, “whats up man” I couldn’t believe how cool he was. He stood with me for a couple minutes, as I lauded and praises to him how “dope” his Summer Jam performance was. He then signed my reciept with the date and his signature which I still have at 30 yrs old lol.

    Could dude, greatest rapper to ever touch a mic, down to earth human.

    Michael on

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