The Drag Queen Ruby Roo

Interview by Lariscious | Photography by Taylor Miller

Ruby Roo hasn’t even been in drag for a year yet, but her rise from “It Boy” to being Glammy-nominated for “Breakout Artist” in 2012 is no fluke. I’ve watched Ruby grow and evolve as an artist in the small, dark clubs of Hell’s Kitchen and Brooklyn over last year and can attest that she is a talent to put on your nightlife radar.

Ruby graciously took time out of her whirlwind schedule of NYU student, nightlife personality, and rising drag star to talk to me for Posture Magazine. Get into it….

Ruby Roo
Ruby Roo

Thanks for a great show tonight! Let’s start at the beginning…..tell us about your nightlife beginnings and you rise to being glammy nommed breakout artist…

Well I started going to clubs when i was 18. I went to the 18 plus nights and Splash and Rush and party called Germs in Brooklyn. At the time i was really into androgynous fashion. I was wearing like oversized t shirts and leggings or wedges. You know that kind of tragic phase that all the small town gays go through when they first move to New York. I was really into bows so I starting cutting the bows off bowties and wearing them on chains around my neck. And then gradually led to me wearing little bow in my hair, which matching blazers or vests or what have you.

I began to get a reputation as the “bow boy” at the parties I went to. And I started wearing makeup and making my look a little more club kid-esque. Then promoters started asking me to work their parties. i was underage and didn’t have a fake [ID] but I’d get in because I was “an employee.” One thing led to another and suddenly the bows on my head were getting bigger and bigger.

Then bows turned into silly head pieces.

Around this time Next magazine started calling me “The It Boy,” a title a well-known drag queen gave me (though she probably wouldn’t admit that she even ever liked me now that i’m also a drag queen).

I’ve always been pretty crafty and really into vintage clothing so I started buying vintage dressed and making headpieces to match. So I’d wear like a giraffe print polyester dress and a little matching pill box hat I used from extra fabric I cut from the hem.

I was always adamant that I was never going to be a drag queen. I liked the gender-fuck thing I was doing. At the time a new wave of club kids kind of hit New York City (though it didn’t really last) and I was always at the premier parties.

But there was something very alluring about being a drag queen and as The It Boy I felt a little stuck. So I asked some friends Misty Meaner and Mocha Lite, who did a shoot with me as The It Boy where I wore a paper bow that was about 6 feet wide, if they’d do me up in drag one day.

The transition was pretty easy because I already had a wardrobe of dresses from The It Boy and I already had basic makeup skills and I already knew all the people in the nightlife scene.

I did drag for the first time on the 4th of July in 2012. Misty made a wig for me that was red with a blonde curl in the front – which matched my boy hair at the time-

and then I just started following them around performing at their events and making appearances at parties. It took some time for people to realize that Christopher Van Cleave was now Ruby Roo, but they caught on

After about two months I was really coming into my own as far as hair and makeup goes. I discovered that I was really good at styling wigs. So Ruby’s “thing” became big hair and vintage dresses.

I was shocked that I was nominated for a Glammy award. The noms came out not long after I started doing drag and the other girls who were nominated were certainly more seasoned than I was but I was really happy to see that collectively the nightlife scene was embracing my transition from club kid to drag queen.

Ruby most definitely has a signature visual aesthetic, but also a unique, modern take on retro performance style, for lack of a better term. Where do you draw your inspiration for your pieces?

My inspiration comes from the musical divas that I loved as a boy. I was “the” theater kid in my high school and by age 18 I’d been in over 30 theatrical productions, and fully intended to pursue a college career for theater. And then I didn’t. But I’ve always loved broadway. Bernadette, Patti, Barbra, Julie, Angela, Judy, Elaine. Basically all women who only need a first name to inspire an image in your mind. Hopefully one day people will say only have to say “Ruby” to know they’re talking about me.

If I had to define my style of performance in one sentence it would be “diary of a man white (black?) woman”

My signature numbers are Rusty’s “Let’s Hear It For The Boy” from Footloose and Effie’s “Move” from Dreamgirls.

Ruby is a classic modern woman from the 60’s. Or 50’s. Or 40’s. Or sometimes 70’s.The Ruby persona is one that is very posh, chic and.. well, rich.But staying very classy all the time.

Another signature number is Patti’s version of “Ladies Who Lunch.”

Ruby isn’t young, she’s hip enough to know what’s going on, but she won’t be found drunkenly making out with someone at the bar or heard singing about pussy. At least not often.

People often associate my look with Betty Draper from Madmen, though I’d like to say I’m Betty with a splash of the show’s sexy secretary Joan Holloway.


Which brings us to your new headlining show “I Love Ruby.” tell us about the concept of this show. How did it come to fruition, and what can one expect from this show?

I Love Ruby is a type of drag show that I haven’t really seen before. Each month I prepare a list of songs for me and my guest host, this month it’s the lovely Elizabeth James, and write a script revolving around a central theme In a sense I’m trying to recreate the feel of a live studio audience filming of a classic 50’s sitcom.

The name comes from I Love Lucy, obviously, so I try to intersperse a few spoken word lipsyncs to classic I Love Lucy scenes, like “Vitameatavegamin,” for instance. Where most drag shows are just a compilation of a bunch of songs that girl wants to perform that night, I’m trying to make I Love Ruby a cohesive evening.

it’s pretty exciting and somewhat difficult!


2012 has been quite the year for Ruby. What other projects do you have planned for the rest of 2013 and where can one see you perform?

The future is a little uncertain. I’m currently based in manhattan but iIm headed to Brooklyn right at the start of the summer so I hope to make myself more present there and just take over.

Right now you can catch me at Hell’s Kitchen’s Vlada lounge on Wednesday nights for Franzia Wednesday with my partner in crime, Hamm Samwich.

I’ll also be at TuTu’s on May 11 for Stiletto’s Up with Elizabeth James

There are some other tentative plans that i’m not really allowed to talk about yet, but this summer is going to be big.

My drag birthday is the 4th of July and I’m planning a debutant ball but the location is still undecided.

Ruby Roo



Posture Magazine
Posture Magazine

Posture is a queer-run art and fashion magazine that brings queer, women, and POC creators to the front.