Ralph Steadman Tip-Toes Towards Another Kentucky Derby

In ESPN short, Sean Penn marvels that Hunter S. Thompson took the Churchill Downs grass and "shoved it down your throat."

In advance of the 142nd Kentucky Derby, ESPN 30 for 30 Shorts gifted us with Gonzo @ The Derby, a look back at Hunter S. Thompson and illustrator Ralph Steadman’s epic coverage of the event in 1970.

For Vanity Fair, Jordan Hoffman dialed up Steadman via Skype, from Kent, England, to chat about those gonzo journalism days. Although Steadman’s visit with Thompson to Louisville was a one-and-done, he has managed to remain connected to the event in another cool way:

“I’ve never been back to Churchill Downs,” Steadman tells me, but he continues to lay a bet every year. “I’m [going in] with one called Tip Toe. I don’t know why. That’s a good name for a horse, though.”

Interesting that Steadman is drawn to bet on that horse by the name. Sure enough, in a piece this week for the Kansas City Star about strange horse names, reporter Lisa Gutierrez reminded that this is how many folks place their big-race horse bets.

There’s one important detail about Steadman’s 2016 Derby pick, which Hoffman shares in the subsequent paragraph and which suggests there’s such a thing as gonzo gambling:

Tip Toe does not appear to be competing in this year’s race, but I’m not going to be the one who tells Steadman. This was the man who sketched deformed portraits of people in 1970 Kentucky and gave them as gifts, nearly causing a fight at a Louisville pool hall. “The bloke I was playing billiards with almost gave me a whack with his stick! He thought I insulted his wife!”

Previously on FishbowlNY
Fans May Soon Be Able to Take the Hunter S. Thompson Ride
The Time Hunter S. Thompson Borrowed a Cup of Donna Rice