paint the town

The Kentucky Derby’s big winner is this gay artist

Wiley Caudill sits in front a patterned wall next to a horse statue. The wall, floor and horse are all overed in painted blue roses.

Saturday, May 4, marks the 150th annual running of the Kentucky Derby. And it’s all about Fierceness.

That’s not only the name of the 3-year-old bay colt who’s this year’s oddsmakers’ favorite; it’s an apt description of the pride and ongoing determination the queer community can feel about being recognized and respected by one of the sporting world’s most venerable red state institutions.

Blue in bloom

Caudill poses in front of a wall featuring his trademark blue roses. He is wearing a hoodie with the same rose motif.

Caudill’s trademark blue roses have made him a popular artist.

The official artist of this year’s Derby is Wiley Caudill, an out-and-proud 27-year-old painter raised in rural Cynthiana, KY (pop. 6,441), who exploded to internet popularity in 2021 after documenting his creation of a wall piece partially inspired by Meryl Streep’s performance in The Devil Wears Prada.

“I love that movie,” Caudill explained in an interview with GayCities. “I had been doing mainly outdoor murals at that point and I decided to paint an interior wall of my apartment to expand my portfolio.

“I wanted to do something that would attract attention on TikTok. I’d always liked painting repeated patterns of roses, so I decided to make a video of that. But instead of red roses, I did cerulean blue, using audio of the speech where Meryl Streep speaks to Ann Hathaway so rudely about that color.”

“You take yourself too seriously to care about what you put on your back,” says Streep in the role of Miranda Priestly,  “but what you don’t know is that sweater is not just blue, it’s not lapis, it’s not turquoise, its cerulean…and you’re also blithely unaware of the fact that…that blue represents millions of dollars and countless jobs.”

Two years later, after millions of online views, countless commissions (well, dozens), and the creation of fundraising art for causes, including the University of Kentucky Agriculture Department’s LGBTQ+ scholarship fund and Lexington Pride, Caudill was contacted by Derby brass.

“I had no idea how they knew about me,” he recalls. “And I certainly didn’t know there was an official artist job! But it turns out they’d had their eye on me for a while because of my roses.”

The Derby is nicknamed “The Run for the Roses” after the horseshoe-shaped bouquet presented to the winner.

 Today, Caudill’s roses and other Derby motifs are prominently displayed in murals at Churchill Downs, the race’s historic Louisville location. His work will be exposed to an audience of millions during the Derby’s television broadcast (2:30 p.m. ET on NBC in the U.S.).

His work is also featured on the cover of the race day program, commemorative apparel and prints, and the labels of race sponsor Woodford Reserve’s annual limited edition Kentucky Derby bottles.

Celebrating inclusivity

Caudill’s mural features roses and other Derby motifs.

Caudill’s mural features roses and other Derby motifs.

“We are incredibly lucky to showcase Wylie’s talents,” said Tonya Abeln, President of race and presenter at the Churchill Downs Foundation. This underscores the institution’s commitment to creating a sense of welcoming inclusivity for Kentucky locals, tourists, and television viewers.

This year, for the seventh time, Churchill Downs sponsors Derby Diversity Week (DDW), which presents a series of programs and panels focused on driving economic impact and social change for minority communities in the Louisville region.

DDW founder Tawana Bain explained to local television station WLKY, “We want everyone Black, white, rich, poor, gay, straight to know that the Derby is for them, and everybody is welcome. We literally erase the invisible line that so many of us live within our day-to-day lives.”

Among the queer highlights of  DDW 2024 will be a “Wigs and Kicks” party at Louisville’s Muhammad Ali Center following the race on May 4. The benefit for local queer organizations, hosted by Olympian soccer star Joanna Lohman, encourages attendees to wear outlandish wigs, a nod to the fanciful hats traditionally worn by Derby attendees.

Fancy fashion and self-expression

Caudill poses in a cheerleaders top and skirt in front of one of his murals.

Derby fan fashion statements have always been extravagant affairs. Caudill is ready to cheer them on.

Eccentric headwear—and Southern style in general—have long had added queer appeal to the Derby. This somewhat underground allure won mainstream acknowledgment in 2014 when blade-running bon vivant Johnny Weir first became a “lifestyle correspondent” for NBC’s race coverage along with his frequent broadcast colleague, Tara Lipinski.

Wylie Caudill says that while he’ll be attending an official Churchill Downs post-Derby party in Louisville this year, gay bars throughout the state host race viewings and after-parties.

“It’s a big time for fashion. You’ve got to really do it up. It’s definitely not like the Super Bowl, where the gays are kind of take-it-or-leave-it.”

Caudill, who always drew as a pastime and began doing elaborate outdoor chalk artworks while studying broadcasting at Eastern Kentucky University, says that his visual flair blossomed in parallel with his coming out.

“It was my 19th birthday,” recalls Caudill. “I remember thinking I could never really feel confident if I didn’t come out. And the same thing eventually happened to me with my painting. I needed to showcase what I love and be true to my own vision.”

“I started to get a lot more mural jobs instead of people just asking me to paint their logos. The best thing I ever did for myself was just to let me be myself.”

State of mind

Caudill, wearing paint stained clothing, shows off another of his murals that features a rabbit wearing a shirt and vest.

A paint-stained Caudill poses in front of another of his murals.

“I love Kentucky,” says Caudill, who lives in Lexington. “I want to stay here. I’d love to own a home in five years, and that’s certainly not going to happen in New York or L.A. I can travel to bigger cities for work if I have the opportunity, but I think its cooler to be from a place where everyone else hasn’t been.”

“And I love being a queer artist and contributing to the queer community here. I had a really fortunate experience growing up in a liberal supportive family, and I know that not every kid in Kentucky has that. But things are changing and I’m glad to be a part of that.”

See more of Wylie Caudill’s artwork at

Queer Kentucky nuggets

Caudill poses in front of a mural painted for Local Kentucky 68 artists' market in Maysville.

Caudill poses in front of a mural painted for Local Kentucky 68 artists’ market in Maysville.

  • In addition to its fame as Derby City, Louisville is heralded as The Disco Ball Capital of the World. Omega National Products, one of only a few companies that manufacture the mirrored orbs, was responsible for 90% of all production during the 1970s and, in 2016, constructed the largest specimen ever, an 11-foot-wide 2330-pound behemoth.
  • In 1907 and 1914, the Derby-winning thoroughbreds were named Pink Star and Old Rosebud.
  • In 1970, the first trial over lesbian marriage took place in Louisville after a couple’s request for a marriage license was denied.
  • Louisville’s first gay disco, The Badlands, opened the night before the 1973 Derby.

Don't forget to share:

Your support makes our travel guides possible

We believe that LGBTQ+ people deserve safe vacations that allow them to be their authentic selves. That's why our City Guides aren't locked behind a paywall. Can you contribute today?

Cancel anytime · Proudly LGBTQ+ owned and operated