A drag persona can be a joke, a shield, a spotlight, or all three at once. We talk with Anthony Smallwood, director of development at LexArts, about what it means to build community through art and what happens when a character like Helena Handbasket grows into “someone” you have to manage, protect, and keep evolving.

We start in the heart of Lexington, Kentucky with LexArts: an arts nonprofit working to make creativity and culture accessible to everyone. Anthony breaks down how fundraising really works, why donations matter, and how grant funding and community review can turn small dollars into real projects, opportunities, and beautification across the city. If you care about Lexington arts, arts education, or how local nonprofits stay alive, you’ll get a grounded look at the mechanics and the mission.

Then we go behind the heels. Anthony shares the origin of his iconic persona, Helena Handbasket--from an LGBTQ advice column to a Fourth of July parade debut, plus what it takes to get ready, why he sometimes sings live, and how drag culture in Lexington has shifted over time. We also dig into drag audience etiquette, the cost and labor behind a three-minute number, and a bigger question: how do we show up as our authentic selves while still making real connections in a complicated world?