Wylie Caudill signs a 2024 Kentucky Derby Woodford Reserve bottle.

Artist Wylie Caudill signed posters, postcards, and Woodford Reserve bottles on Saturday, April 13 at The Main Cup. The Cynthiana native was chosen by both Churchill Downs and Woodford Reserve to create artworks for the 150th running of the Kentucky Derby.

The Main Cup was the place to be in Cynthiana on Saturday morning. People lined up out the side door and all the way down the sidewalk to the parking lot of the Presbyterian Church.

While the coffee and treats at The Main Cup are top notch, the draw on Saturday was local son Wylie Caudill. Caudill was in town to sign the artwork he created for Churchill Downs to commemorate the 150th running of the Kentucky Derby.

At one point, at least 100 people and two dogs were queued up, many toting multiple bottles of Kentucky bourbon. Woodford Reserve commissioned Caudill to do the artwork for their special edition 2024 Kentucky Derby bottle.

This is the first time the same artist has been commissioned to do the artwork for both Churchill Downs and Woodford Reserve. Caudill is also the first muralist chosen for the honor.

Caudill was all smiles as he signed posters, post cards and bottles.

Bob Nettles, there representing Churchill Downs, stood next to him, rolling posters as fast as he could and putting them into protective cardboard tubes. He marveled at the community turnout.

Caudill’s mom, Amanda Smith Caudill; and aunts Meg Ammerman and Tallu Smith were on crowd control duty.

Although he had a couple of previous small signings, this was his first big event.

Early on, he peered out the window at the growing line of people. Later, told about the length of the line, he laughed, “I can’t look out the window; I’ll throw up.”

Caudill signed for two solid hours and posed for lots of photographs. Many people he knew. The ones he did not know seemed eager to forge a connection.

“You did a job for a friend of mine.”

“We know your mom and your aunts.”

“My daughter Teresa told me to tell you ‘Hi!’ ”

“I taught you in school.”

“My wife works with your dad.”

“I went to school with your mom.”

“I kept you in the church nursery.”

Caudill never failed to be gracious and appreciative.

“The community means so much to him,” his mother said.

Cynthiana has benefitted from his talents; several of his murals grace local buildings, but the Derby commissions have unquestionably boosted his career to a new level.

The 150th Kentucky Derby painting will not be forgotten soon. The same day Caudill signed posters in Cynthiana, a huge banner depicting the painting was hung on the side of the Stark Building in Louisville that WDRB news reported is eight stories tall.

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