Your 2008 Kentucky Derby Dumbassery Roundup

For us, the Kentucky Derby is an opportunity to relive Hunter S. Thompson’s well-documented 1970 trip to enjoy the masterpiece of Southern life and horse racing. Therefore, welcome to our yearly attempt to live up to the Gonzo search for the Kentucky Derby ideal:

Hunter S. Thompson

“So the face I was trying to find in Churchill Downs that weekend was a symbol, in my own mind, of the whole doomed atavistic culture that makes the Kentucky Derby what it is.”

We’ll do our best.

On our trip south, let’s make a pit stop in Long Island, NY, where a charming couple chose to stop into the local off-track book to enjoy the Kentucky Derby. How grand, right? Unfortunately, they left their two-month-old in the car during the 20-minute stopover. Police frowned upon that; both have been arrested.

(It’s okay, though, officers! The mother left the heat on in the car. It’s like a baby chicken egg.)

That’s an auspicious start; let’s look at the celebrities and locals that graced Churchill Downs with their “pretentious mix of booze, failed dreams and a terminal identity crisis”. (Thank you, Hunter.)

Each May provides the only opportunity available to the LOUISVILLE COURIER-JOURNAL gossip writers to tackle the A-, B- and C-list celebrities that most flyover states never get to see outside of the occasional film shoot. We’re not sure any of them travel to Churchill Downs for reasons they understand, but there they are, knobbing hobs.

We peek into the (we guess) traditional “Barnstone Brown” party, where (God help us) the Barnstables and the Browns somehow combine forces like a Southern Voltron to create the soirĂ©e of the season. How do we know it’s classy? Darryl McDaniels from Run D.M.C. acted as DJ.

D.M.C. at the Kentucky Derby

(Is anyone else remotely uncomfortable with the notion of a black man being brought in to entertain a gathering of rich white people in Kentucky? Just us? Okay.)

And how do you know it’s a great party? Ask Larry Birkhead:

Larry Birkhead at the Kentucky Derby

“This is where I met Anna Nicole (Smith) … so it’s always important to come here because it just feels like it’s home.”

Ask us again why Hunter S. Thompson did so many drugs. We have an inkling. Please read the whole article for all the celebrities (including Tom Brady) so we don’t have to.

Other signs of the impending apocalypse (pictures from THE ANGRY T):

  • Michael Strahan and his new model friend made a very active effort to disprove at least some of the rumors spread by Strahan’s ex. You may apply horse jokes here at your own risk.

Michael Strahan and a model

  • There was something called a “Crown Royal Playboy Lounge Party”. That’s what we like to call “truth in labeling laws really work”. All the athletes were there, including MJ, Oak, Dr. J, etc, etc, etc. It must have been like Gold Club Old Home Week.

Michael Jordan at the Kentucky Derby

(David Stern just sent Jordan a pitching machine out of habit)