And They're Off! B-List Celebrities in Big Hats Chomp Down Hard on Old Kentucky Home

“And unlike most of the others in the press box, we didn’t give a hoot in hell what was happening on the track. We had come there to watch the real beasts perform.”

– Hunter S. Thompson, The Kentucky Derby Is Decadent and Depraved

As Delta flight 1624 taxied along the tarmac at the Louisville Airport on the evening of Friday May 4, its occupants craned to get a glimpse of the conditions.

It had only recently stopped raining, and some rays of sunlight were now peeking through the remaining shreds of cloud.

“Oh my, did you see that big rainbow over there?” an older woman asked her twentysomething son. Their journey to the Derby had begun earlier that day in the Florida Keys. “Wonder if there’s a pot of gold at the end of that rainbow.”

“Look at all those private jets,” replied the son, Jake, now gazing out the window. He had missed a prime weekend of wake boarding with friends in Orlando to make the trip.

Indeed the giant rainbow had ended in a mass huddle of private jets, no doubt the mode of transport for the rich and famous who now descend on Louisville each year on Derby Day.

“You know the Queen’s gonna be here,” said the mother, who spoke in a thick southern accent.

Mother and son had not come down solely for the star-gazing.

“I’m going for Scat Daddy,” said Jake.

“Kid love the slop? Mother was mudder? Father was mudder?” offered the Observer, referencing an episode of Seinfeld, and the bad weather.

“What?” came the response.

“What the hell did you leave a small town like New York to come down to a big city like this for?” joshed a portly cab driver on the drive into downtown Louisville, pronounced “Loo-a-vul” by the locals. “Don’t make a lick of sense,” he said. “That’s an expression.”

The cabbie’s joke belied an obviousif increasingly senselesstruth about his hometown on Derby weekend: for two long days, Louisville, population 256,231 at last count, is converted into an international city.

At its core, of course, the weekend is about a horse race. The Kentucky Derby, billed as the oldest sporting event in the South (date of birth: 1875), has almost since its inception drawn racing fans from across the country and the world. The typical crowd at Churchill Downs is around 155,000. This year 156,635 fans would pack the stadium – a good turnout, but nothing extraordinary.

What does appear to be changing is the crowd populating the boxes of “Millionaire’s Row”. While the Run for the Roses has always drawn big names – Presidents Bush and Nixon, Babe Ruth, John Wayne, Jack Nicholson – the arm’s length list of famous faces clogging up the choice seats this year included the likes of O.J. Simpson and celebrity inseminators Larry Birkhead and Kevin Federline.

More notably the weekend is overrun with celebrity-driven parties and events — the types of orgies of cross-promotion and celebrity protectionism that tends to invade any and every annual event these days, especially the ones larded with jet-setting young folks.

“Ladies and gentleman, Nick Lachey,” said a man in a tuxedo from a stage out in front of Cyb Barnstable Brown’s mansion later that evening. Local gawkers, crammed in a pen adjacent to the red carpet, began chanting, “Nick, Nick, Nick, Nick.”

“Ladies and gentlemen, Vanessa Millo,” said the announcer, butchering the last name of Mr. Lachey’s girlfriend, MTV personality Vanessa Minnillo.

A long pathway leading up to the sprawling house was lighted by various stages on either side of iteach with a different makeshift backdrop in the theme of a Broadway musical, and a different troupe of young girls singing and dancing their little hearts out. The house itself was adorned with Christmas lights. The party’s theme this year was “That’s Entertainment.”

And They're Off! B-List Celebrities in Big Hats Chomp Down Hard on Old Kentucky Home