Florals for spring? Groundbreaking. Kentucky’s newest sweetheart yassifies a Derby tradition

Contrary to popular belief, The Kentucky Derby has always been queer. Big, boisterous hats and flashy fascinators paired with dresses in bright pastels, deep rosy reds and Kentucky blues fill Churchill Downs from the infield to Millionaires row. Let’s face it: it’s one big drag show.

For the Derby’s 150th anniversary, Churchill Downs and Woodford Reserve commissioned openly gay artist, Wylie Caudill,  to bring his trademark rosette imagery for the latest design of the famous derby poster and bourbon bottle. Needless to say, we were absolutely gagged.

Originally from Cynthiana, but now residing in Lexington, Caudill told Queer Kentucky  that Woodford Reserve and Churchill Downs had been watching him and his viral social media posts for quite some time before approaching him with the brand deal in January  2023.

Caudill’s work went viral in 2021, when over 6 million TikTok users watched Caudill painting a mural of cerulean rosettes with an overlaid audio of The Devil Wears Prada’s Mirana Priestly (played by Meryl Streep) delivering a memorable line about a cerulean sweater.

“I think we need a jacket here…,” Streep’s voice is heard saying.

Caudill  soon began posting  videos of himself painting Woodford Reserve bottles with the famous rosettes. It didn’t take long before the bourbon powerhouse brand scouted the painter — the rest is queerstory.

“For such a momentous occasion for Derby 150, we wanted to feature a Kentucky artist whose work felt different than our past Derby bottles,” said Chris Poynter, public relations and partnerships manager for Woodford Reserve and Old Forrester. “We fell in love with Wylie’s artwork. And we fell in love with Wylie and his charming and witty personality.” 

Caudill promoted the partnership beyond his contracted scope of work without hesitation, explaining that he loves showing his work to the world on  social media. More specifically, added Caudill, he loves showing Kentucky to the world.

“I don’t just ‘do’ paintings,” he stressed. “I do social media. I paint on bottles. I live-paint murals and I was determined to go above and beyond what Churchill Downs and Woodford Reserve have ever had with an artist before.”

While  the two brands were in love with Caudill’s viral work, the process to find the perfect design for Derby 150 didn’t come without challenges. Caudill admitted he had little knowledge of Bourbon — or horse racing — which required hours of research to deliver an authentic design that celebrates the Derby’s long, rich history. 

“I didn’t have much of a relationship with Bourbon or the horse industry before this,” he said . “I grew up with old retired thoroughbreds in my backyard, but I was never immersed in the culture. They were just these mean old animals in my backyard that I had to feed.” 

Throughout the whole process, which started in June of 2023, Caudill submitted close to 30 designs to Woodford Reserve and Churchill Downs — many of which were rejected by the brands because they were “too busy” and didn’t encompass enough of the style he was known for. 

Two weeks before his deadline, he was told that Woodford Reserve and Churchill Downs wouldn’t be sharing his  design as originally planned. Instead of having a shared design,  they would now each  have their own.

“Churchill went with the trophy design and Woodford went with the red rose horse,” Caudill  explained. “I had two weeks to paint them. I am quick, but I’m really really stubborn when I start a project. I can do 16 to 18 hours a day for a week straight and these paintings normally would take three weeks each.”

Once the final designs were submitted and approved, Caudill waited over a month in anticipation for the design’s release took a toll on  his nerves. He vowed not to  look at any of the online critics. 

When the brands soft-launched the designs on social media, he recalled  some of the comments having an effect on him: “Roses aren’t blue, what’s going on?” one commenter asked. 

Then the final designs dropped. As Caudill remembers, the reception took a drastic change for the better — and he took a huge sigh of relief. “I was actually told to read the comments because they were so good,” he said with a chuckle. 

His hard work for Derby 150 earned Caudill a new kind of brand recognition that’s given him a new fan base, and a solid boost in sales for his personal paintings. Within weeks of the release of the designs, his online store sold out. 

Oh, and did we mention he’s humble too?

“They like me, they really like me,” he quipped while doing his best Sally Fields impression.