

This Mother’s Day, I spent the morning with a completely different caliber of woman than the one who birthed me.

It’s 6 a.m. at the Luxe Hotel in downtown Los Angeles and Derrick Barry perkily welcomes me into his room wearing nothing but a white towel, the red waistband of his Calvin Kleins peeking out from underneath. Fans of Logo’s gender-bending competition series RuPaul’s Drag Race may recognize the svelte blond by his alter ego Derricka, this season’s resident Britney Spears impersonator. Barry, along with the show’s current and former cast members, is in town for the second annual RuPaul’s DragCon, the world’s first and foremost convention for all things drag, held in the L.A. Convention Center across the street. Barry was kind enough to let me shadow him as he morphed from Derrick into Derricka.

After a quick shave, Barry begins the makeup process by focusing on his eyes.

“I love starting with eyes, because it takes the longest, so I like to knock them out, and everything else is just faster,” says Barry, as he smears a tube of purple goop across his brows.

“This is an Elmer’s Glue Stick,” he explains. “You go against the hair and then up to cover the whole brow. I don’t usually do this for Britney, but this is DragCon and everything needs to be heightened. People are coming out for the full fantasy.”

The foundation of Barry’s makeup knowledge can be traced back to Halloween 2003, when he had yet to come out of the closet, let alone be initiated into the mysteries of drag culture. His then-girlfriend’s cousin was a makeup artist who glammed him out as Britney Spears for the occasion.

“The reactions from people were crazy. We got in a car accident on the way to [a Halloween party]. I went into a restaurant to powder my nose, because that was obviously what I was worried about in drag. I started singing Britney’s 'You Drive Me Crazy,' in this candlelit romantic place, and people stood up and applauded. I’m like, ‘OK, this is something I have to see what I can do with.’”

Barry showcased his uncanny resemblance to the pop star, first on an episode of The Tonight Show in which Britney was a guest, and later, and more prominently, as a contestant on the third season of America’s Got Talent. From there, he was cast in An Evening at La Cage at Las Vegas’ Riviera Hotel & Casino, where he impersonated Ms. Spears professionally. Sin City also encouraged Barry to discover his true sexuality in a supportive environment.

“I moved to Vegas when I was 21. The cast was gay, I was surrounded by drag queens, I went out to gay clubs,” said Barry, now applying a whitish substance to his face.

“This is Kryolan. After the brows are set with glue and powder, then you go over your whole face with a Kryolan paint stick. It covers everything. We can’t start a blank canvas without putting down a primer.”

The art reference is apropos. Barry’s longtime boyfriend is Las Vegas–based painter Nick San Pedro, whose oeuvre heavily depicts images of iconic divas such as Mariah Carey, Janet Jackson and, not surprisingly, Britney Spears. While Barry applies Kryolan to his T-zone in the bathroom, San Pedro flits around the hotel room, juggling making instant coffee, prepping a hot-pink wig and ironing a beauty-queen sash.

The couple met in 2005 at a Pamela Anderson fashion show in Vegas. A native of Sin City, San Pedro helped Barry cut the line to get into the event, and they’ve been inseparable ever since. But the artist’s influence on the performer transcends social perks.

“When I met Nick San Pedro, I felt I was living a black-and-white life,” said Barry. “There wasn’t a lot of color, literally. When I moved into my house, I didn’t paint any walls because I didn’t want to be locked down to a color. It scared me. When he moved in, a year after I got the house, we started painting: a bright pink wall, a blue and brown and silver striped hallway. Things I never would have done. He made me realize that life is more beautiful in color.”

Barry is now applying powder to set his face.

“I did two foundations, darker and light. One is all-over coverage, then the highlight is added. The highlight makes you pop.” As Barry says this, Mackenzie Claude, the third and final member of their family, enters the room.

Identifying as a “trouple,” Claude was added to their relationship about four years ago after Barry met him through his ex-boyfriend. Towering at 6-foot-5 (and that’s without his heels on), the baby-faced Amazon sports a Barbie-pink dress that belies the six years he served as a military medic. Claude was inducted into the realm of gender-bending during the fifth season of Drag Race, during a challenge where contestant Alaska Thunderfuck had to give a military veteran a makeover. Claude’s nom de drag, Nebraska Thunderfuck, is a nod to this lineage.

“When he got the call, I was like, ‘You gotta do it,’” says Barry. “He was like, ‘I don’t know. I’ve never done it. It feels super weird.’ I’m like, ‘Yeah, feeling weird is the fun of it. You should challenge yourself.'”

At this point, San Pedro reminds Barry that it is already 6:59 a.m. Barry's call time for the convention is 9 a.m.

“Plenty of time!” Barry beams, dabbing a brush into a jar of magenta powder. “This is a blush I use as eye shadow. Since we are giving ‘Showgirl Pink Fantasy’ today, we are putting pink over the whole lid area.” Then, slipping into a sassy drag affect, he adds, “I wanna give the childrens some drag.

“The thing is, this may be the one event some kids come to all year. It's their big-ticket item. There was a girl who came out to her family because of Drag Race. It's such a powerful statement. That’s what RuPaul set out to do,” Barry says, blending the hot-pink blush with a lighter shade before smoking out the corners of his eyes with touches of black. It's apparent that he has been diligently adding to the makeup skills he gleaned from his girlfriend’s cousin over a decade ago.

“I just did Miss Fame’s class. She used me a model. I learned so many tricks from her. She does these classes called ‘Painted by Fame’ — I say ‘Touched by Royalty.’ She’s the best in the business. There is so much to learn from other girls in the business. Everyone has a different knowledge. It's like working with different directors, or choreographers,” Barry says, putting the finishing touches on his eyes.

“This is a sparkle dust with white. Then I will go in with black eyeliner. Any black you add will make everything bigger. I love black eyeliner, and liquid eyeliner is so clean.”

For Barry, evolving as an artist is arguably the most challenging and the most motivating aspect of his art form.

“I should be doing more than last time. I can’t walk out there with the same face every time. It's boring for me, and if I’m bored, the audience is bored. The challenge is to keep yourself entertained.”

Nick pops his head in, informing us it is now 7:38 a.m.

“We’re doing great. Yesterday I did it in two hours!” Barry announces, finally finishing with his eyes. “Now, we get to do the fun part, which is all the face contouring. I contour with a light brown, like a soft beige. I go in on my jawline, because I have a big one … jawline,” he clarifies. “I take this flat brush and draw on a new jawline, a more feminine, sexy one. I bring it all the way down to the chin. You can do this with creams and powders. I prefer powders, but I will probably switch to cream because it blends better and lasts longer. Powders soak into your skin, and creams are foundation. The consistency lasts longer.”

Barry then retraces these lines, first with gold leaf, then soft pink with a fan brush to add color. As he creates these gentle lines, he reviews the hectic week ahead. After the convention wraps tonight, he will spend the entirety of tomorrow in rehearsals, leading up to the season-finale shoot on Tuesday. Coincidently, it will be filmed at the Orpheum Theatre, the same venue in which Derrick auditioned for America’s Got Talent.

“So full circle for me. It's weird how the universe works. I auditioned for season seven, I didn’t hear back, and then I got season eight. I needed that extra year.”

Focus now shifts to Barry’s nose.

“Now I’m highlighting the nose, and I’ll go in with the contour. Same contouring color, I go in with an angle brush. I connect those lines up to the brow. Now, Britney has a wide bridge, so the space in between her eyes is pretty big.”

At this point, the transformation becomes more apparent. Though the illusion of makeup, Barry truly seems to shapeshift into Britney. Next come the lips.

“I’ll use a bright pink, and I’ll line with the color I used on the eyes. I’ll start with the lip liner. Now I take the brush I used on my brow, it's a double-duty brush, and I get it wet and I dip into that rouge. This is Frambrosia, it's my favorite color from La Femme [cosmetic line].”

The grand finale for Barry’s face is the application of eyelashes.

“I use weave glue as eyelash glue. It dries quicker, and in Vegas we have changes that happen extremely quickly. There are times where we have one number [to change our look]. We are not playing around.”

Now comes the last bit of makeup magic necessary in the transformation from male to female: the illusion of breasts.

“Because I’m wearing the nude body suit, I’ll put some boobs on. I use my same contour brush, and draw on my boobs. I follow what I see in the mirror, what they'd looks like if I were to push them together. I’ve been doing it so long it's like muscle memory. I always start with lighter contour and work my way up. But you want to keep it light, because they’d be real shadows on a girl.”

For the next step, I leave Barry alone in the bathroom so he can “tuck,” the term for removing the visibility of one’s penis. The process involves pushing the testes up into the body and pulling the scrotum and phallus back toward the perineum.

“It's never anything comfortable or fun, but now that I’ve been doing it for so long I can’t imagine performing without that,” he says. “You have to. It's part of the illusion.”

The bathroom door opens, revealing Barry, now clad in a pair of pantyhose, sans bulge. Studying himself in the hotel room’s full-length mirror, he adds foam padding to replicate the hips of a woman, followed by two more pairs of hose, to conceal the pads. Finally, he takes out a strip of nylon.

“Now this is a piece that not everyone uses, and I don’t understand why. It's the top of tights that you cut, and I pull it down and around, so that way it creates, like, a real va-jay-jay.”

With his southern hemisphere complete, Barry moves onto his chest, donning a bejeweled bra.

“I do my own crystalling. This has over 2,000 crystals. I worked on this, on and off, for almost a week. Some days that’s all I did. But that’s fun for me.”

As San Pedro zips Barry into his ensemble, a sheer body suit studded with pink gems created by House of Gaga stylist Perry Meek, the drag artist ruminates aloud about the double-edge sword of perfectionism.

“It gets in the way sometimes. That was one of the hardest things I went through on Drag Race. I wanted to create things that would last forever, and that I was proud of. I don’t make things quick. That was the biggest challenge I faced. I get mad if it's not perfect. But I think that’s how you make it to the next level — attention to detail.”

San Pedro reminds Barry that it is already 8:46 a.m., and the breeziness of the past 2 hours and 45 minutes evaporates when their preparation hits a snag, literally. Problems with Derricka’s neon-pink wig bring the morning to a screeching halt.

“It came out super different than I thought it would,” Barry laments. “Any time you steam lace fronts, it can curl. It's not fun to work with, it's so fragile.”

The blare of a hair dryer muffles a tense, overly polite exchange between the boyfriends.

“Everyone’s being on their best behavior because you’re here,” Claude whispers into my ear.

Forty-five minutes, a can of hairspray and innumerable bobby pins later, Barry emerges from the bathroom as a fully formed Derricka. From there it's a quick shuttle ride down the block to the Convention Center, where Team Derricka assumes its place at the assigned table. Within minutes of their arrival, a line forms filled with fans of every size, shape, race and, most importantly, gender.