"Has Anyone Ever Cried Here?" Inside A 7-Hour Drag Queen Makeup Class

Four hours into an Intro to Drag Makeup class held in the basement of the Kryolan makeup store in Greenwich Village, 22-year-old Connor Martin reached his breaking point.

He had been instructed to use a product called Pros-Aide, a sticky substance professional drag queens use to glue down their eyebrow hair so they can paint a more exaggerated brow on top, but it kept clumping. "I have oatmeal where my eyebrows were," Martin said, miserably. The class's teacher, professional makeup artist Derek Medina, offered encouragement: "As long as it looks good at a distance in the dark, then you're good."

"I'm going to have a meltdown," Martin announced to the room. "Has anyone ever cried here?"

While regular attendees of this particular class vary, on a Tuesday in early October, the group was comprised of eight people: two professional makeup artists, one actor looking to understand drag makeup for a role, and five drag fanatics who have had minimal to no experience with drag themselves.

This level of interest, especially from people who aren't professional drag queens themselves, didn't exist 10 years ago. "I’ve been doing [makeup] for almost 20 years, and the first thing that most women used to tell me when they sat in my chair was, 'I don’t want to look like a drag queen,'" Medina says. "They don’t say that now. Now they’re saying, 'Yes I want to be highlighted, contoured. Bake me. I want two and three pairs of lashes.'"

Thanks to the ever-broadening popularity of RuPaul's Drag Race, drag queens and the makeup they typically wear has hit a pivotal moment. Things like contouring and highlighting, which are essential to the drag aesthetic, are now a part of the mainstream. These days, as Medina implied, one pair of lashes just isn't enough, and many of his clients favor an intentionally dramatic overall transformation of the face.

That's largely why Tomomi Sano and Ana Carolina Betti, both professional makeup artists with no drag queen clients as of yet, signed up for the course. They've seen the intrigue around this kind of makeup on platforms like Instagram and YouTube, and know that having "drag makeup" as a skill could get them more clients.

But the goal for many other attendees of this class was far more personal. As Medina announced when the day began, this is where so-called "baby drag queens," some of whom are so amateur that they haven't even landed on a drag name, learn how to be taken seriously. That's exactly what Mo Ismail, a 25-year-old CVS pharmacy tech who's gone out a handful of times as Shawna Dontelle, was after. "I’ve never had someone teach me," Ismail says. "All I saw was what was on RuPaul's Drag Race and YouTube tutorials. With performing, I’m a perfectionist: I want to make the crowd roar. And to be great, I have to get this makeup down."

For 28-year-old Manhattan-based attorney David Bethea, this class represented a milestone. A longtime lover of drag ever since he came out at 22, he's frequented drag nights at bars and binge-watched every season of Drag Race with his husband. Four years ago, he promised himself that for his 30th birthday he'd have a huge drag bash, which he'd attend in full drag himself. "I plan on looking fierce, but I just have to figure out what that means," Bethea says. "My friends and even husband say that I don’t have a face for drag, but I was like, Well, maybe it’ll be possible that they paint me pretty."

The seven-hour class was cut up into sections. For the first hour and a half, Medina completed a start-to-finish drag look on the model, a drag queen named Digna. Even as a professional, it took 30 minutes for Medina to mask one of Digna's eyebrows. It took another 30 minutes to contour half her face. With each new product and technique, the students would quickly scribble down tips in their notebooks (Bethea filled up more than four pages in the first hour), and got up out of their chairs to capture pictures with their phones.

After Medina put the finishing touches on one half of Digna's face, leaving her with candy-red lips and four pairs of lashes, he announced that it was time for the students to recreate the look on themselves at the Old Hollywood-style vanities at each of their stations.

While Bethea admitted that he had never put makeup on himself before, people like Jackie Ivers, 24, and Nicholas Lord, 25, were more experienced. The couple, who married this summer, had first done drag together last year at Drag Con in New York City, and both had landed on names: Jackie O'Nasty and Sally Holes, a naughty nod to Sally Bowles from Cabaret.

"Drag makeup is so elaborate and so difficult and so hard to start doing," Lord said before putting on makeup himself. "I don’t want anything too elaborate. Right now, I could go into a club and not feel like a total amateur, but I want people to take me seriously as a queen rather than a boy playing with makeup."

The eight students attempted to follow Medina's sequence, starting with brows, moving onto contour and powder, blending, and then having a bit of fun with eyeshadow and lipstick if time allowed.

Trey Gerrald, a 32-year-old actor, immediately found that his background in theater gave him an edge. This month, he starts rehearsals for the play With Bells On, in which he plays a drag queen named Natasha, and so he attended the class in an effort to figure out how, exactly, Natasha should look. "In the play, Natasha is on her way to a Christmas pageant, so she’s on a budget and she wants to be very glamorous," Gerrald said, while brushing his blush way, way up on his cheekbones. "I've done makeup tests for the stage, but never anything like this."

Regardless of experience, there were mishaps around the room. Bethea attempted to blend his contour with a tissue. Ismail painted his face entirely the wrong shade. Gerrald drew his brows far too high. Martin found he was allergic to something in the makeup, so tears continuously rolled down his face.

Nevertheless, Medina did his best to flutter around the room, going from person to person to address their specific concerns and insecurities. "Drag makeup is an extension of your personality," he assured them. "You wear as much or as little of it as you see fit."

Six hours in, and that affirmation was taken to heart by the students, who finally stopped trying to copy Medina's "perfect" drag makeup, and instead moved on to creating something they loved. Maybe their brows were too high, and maybe their lips were too bright, but each of them landed on a look that felt true to them — whether that was a 1930s jazz singer or a brash redhead. And really, that's what drag is all about.