Roscoe's Presents: Chicago Entertainer of the Year 2026

Roscoe's is crowning Chicago's best this year, and the competition is the real draw — watching the city's most talented drag performers bring everything they've got to the stage in one night. It's the kind of show where you're on your feet, the energy is electric, and you actually care who wins because you've just watched them prove why they deserve it. May 18th at 7pm is when the community gathers to celebrate the performers who've made Chicago's drag scene what it is.