24 Hours With The Ever-Evolving Cheshire

Cheshire goes by Connor Moran when not performing. The 20-year-old used to disagree with the world of drag, thinking the makeup was obnoxious and not understanding why drag queens couldn’t “just go for normal hair, normal makeup, normal whatever.” 

But after being brought to a drag show by a friend, Connor’s mindset changed completely. “I slowly discovered the art aspect of it, and I ended up really, really falling in love with it,” he said.

Cheshire began performing in drag shows in May. This newfound adoration embedded itself to every part of Connor’s life, including his YouTube channel, weekend plans and daily schedule.

6:30 a.m. Connor wakes up before the sun does, makes breakfast (typically eggs) and drives to school, where he takes cosmetology courses.

7:30 a.m. Class at cosmetology school starts. Having originally learned doing makeup through YouTube, Connor continues to refine his knowledge through cosmetology classes. “I started doing makeup before becoming a drag queen. By having that base, I was able to do more stage-type makeup.”

3 p.m. Class ends, and Connor starts preparations for his performance later in the night. “Once I get back to my house, then I’ll get my outfit together,” he said. 

6 p.m. The makeup fun begins. “I take forever. I’m too much of a stickler for details.”  Specializing in makeup and wig styling, Cheshire’s creativity is communicated through her performance looks. Her drag style is Victorian, futuristic and has sci-fi elements.  She’s known to add unique touches to her appearance through features like red skin, syringes and plastic bloodshot eyeballs.

8 p.m. Makeup is finished. Now it’s time for Cheshire to drive to the show venue and mentally prepare for the night ahead. While Connor used to live closer to Gainesville, he recently moved and now travels two hours to perform in venues like Maude’s Café.

10 p.m. The venue requires performers to arrive at least an hour before the show begins. Between call time and the beginning of the show, drag queens have an hour to finish getting ready, stretch and rehearse their act. “I’ve been called the exorcist of drag. I like to incorporate a lot of jarring elements like backbends and mild contortionism.”

11 p.m. It’s showtime. “I enjoy selling a fantasy. [Drag queens] get up onstage and allow people to temporarily disband the reality.” Cheshire performs her heart out to songs like Billie Eilish’s “Bad Guy” or anything Ariana Grande. “It’s so liberating, just being able to play with aspects of gender,” she said. After her set, Cheshire does a final walkthrough, joined by the other queens who performed.

1 a.m. Most people would dread having to drive two hours in the middle of the night but not Cheshire. “All I get to think about is my next performance.” She thinks about which parts of the act need some practice and which worked well with the crowd. “It makes me so excited for the next one.” All of the dancing and lip-syncing can build an appetite. Cheshire typically frequents Taco Bell for a late-night crunch wrap before heading home. This juxtaposition of a drag queen in full glam getting a lipstick stain on fast food emulates the same level of allure as 2006 Fergie in her song “Glamorous.”

3 a.m. As the night finally comes to a close, Connor goes to sleep, ready to do it all again the next day.