Gary Singleton: Bringing Comedy to Clarksville

In this podcast interview, military veteran and entrepreneur Gary Singleton shares the story behind launching Joker’s Comedy House and The Grill in Clarksville, Tennessee. After retiring from the military and working in real estate, Singleton recognized the city’s need for more live entertainment and converted a former restaurant into a full-service comedy venue. The club now hosts weekly improv shows, open mic nights, and touring professional comedians while also spotlighting local talent. Singleton also prioritizes community involvement, organizing monthly charity events and supporting other small businesses. His vision is to build a true “comedy house” that helps grow Clarksville’s arts scene while giving residents a high-quality night out.