We All Start Somewhere: Reliving Jay-Z’s First Visit To The Hamptons

These days, we think nothing of Jay-Z having breakfast with Mayor Bloomberg, brokering deals to move NBA teams, running record labels, vacationing in Italy, and generally being the most ballin blue blood in the universe. But it wasn’t always such a perfect fit.

This weekend I’m making my first visit to the Hamptons to stay at a friends house, and I can’t help but remember this New York Magazine piece, which details the adventures of Jay on his inaugural jaunt to East Hampton. This was back in 1999, mind you. When Jay-Z was still a “thug” in the eyes of many. As he said then:

“I mean, the Hamptons is cool. It’s very serene, a change of pace, a kind of getaway, you know what I’m saying?”

He couldn’t just stay anywhere, though:

The $20 million, 30,000-square-foot, Italianate stucco house sits on eight-and-a-half acres of land and is equipped with an indoor-outdoor pool, tennis courts, a spa, a 120-seat screening room, and a canoe and rowboat to tool around Georgica Pond ... Former renters include Madonna, Warren Beatty, and Kevin Costner (when he was hot). Meg Ryan and Ed Burns were neighbors this summer, and Sandra Bullock was next door in the estate’s smaller farmhouse, known as Main Street.

What happens when hip-hop takes over the Hamptons? Well, after the cops were called to break up Jay’s 4th of July bash, the guests late-nighted in his villa’s movie theater.

After that, it was a screening of Queen Latifah’s Set It Off in the house’s movie theater. Around 30 people remained, including Bullock, Puffy (sticking close to Bullock), Lil’ Kim, and Adrien Brody, the sloe-eyed actor in Summer of Sam. The reveling continued into the wee hours. “Ally b.” -- or Bernstein, another Lizzie Grubman flack -- “was buggin’ out,” Dash says.

“We sent her into the kitchen,” says Jay-Z, “and gave her some cornflakes.”

And Jay-Z talks about what it meant upon his return:

“I’m coming back to Marcy and saying, yeah, you know, Ivana Trump, she’s talking like this, and Sandra Bullock, she’s crazy cool. I’m sharing my experience.”

“Sandra Bullock is crazy cool! Y’all seen While You Were Sleeping? That sh*t is dope!”

But seriously, it’s kind of amazing to read all this with the benefit of hindsight; knowing that Jay-Z has gone from an awkward interloper with the elite to being maybe the most recognizable entrepreneur in New York City. In 1999, he was overcharged for his rental, and scared off the locals. In 2010, you have to think just about any place in the Hamptons would kill to have their name associated with the Jay-Z, to say nothing of the inevitable fawning from locals. A lot can happen in a decade... If you’re Jay-Z, at least.

Anyway, read the whole thing. We should all want to “debut” on the Hamptons the way Jay-Z did. As his partner Damon Dash explained it, ”“Do I want to see someone get shot in his ass, or do I want to get on a private helicopter and fly to the Hamptons?”

Pssh... I’ve seen enough ass shootings this summer. Time to go to East Hampton, son.