On Point With: Shirley U. Jest

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This big-hearted retro pixie just won a major singing drag queen competition, and she’s about to get her own show in the West Village! Shirley U. Jest talks up Thotyssey about cute hats, the truth about singing and drag, and everything else under the sun (and the shade)!


Thotyssey: Hi Shirley! I have to start with telling you that you have probably my favorite drag name of all time. It’s, like, so simple and obvious, but so brilliant at the same time. I bet you had the name decided long before you tried on your first wig, right?

Shirley U. Jest: Thank you, I appreciate that! You’re also not wrong. About four to five months prior to my planned arrival, I was sitting in a bar thinking up names for myself. I’ve always loved the movie Airplane! (which should tell you something about my humor), and “don’t call me Shirley” was what spawned my name.

I was hoping you’d say Airplane!. So anyway, you were recently singing the praises of Sutton Lee Seymour’sThe Way Off Broad,” which just wrapped up at the Beechman. You’re a fan and friend of Sutton’s?

Funny story actually: one of my first official jobs after moving to the city was working the front desk at Pearl Studios, and Sutton and I were co-workers. She had just started dabbling, and it was that fall when she won “So You Think You Can Drag.”

I’ve always admired and looked up to Sutton as girls from the same camp. To this day, I still pop into her shows to see how amazing she’s become.

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Where’s your hometown?

I’m originally from Ohio.

When did you come here?

Three and a half years ago.

Did you go to school here, or there?

I went to the College of Wooster in Northeast Ohio. Matter of fact, I didn’t end up here until after three years of living in DC trying to be a teacher.

It is certainly not a good time for the job market in academics, unfortunately. 

You are very right, and that is partially why I moved [to New York]. When I didn’t get the work as a teacher, I did what I always did, which was find somewhere, anywhere to perform.

After a while, that started to make more sense than teaching. I figured that if I wanted to make a real go of it, I should go to a city where I could give it a try. And I always loved New York more than anywhere else, so I did what only made sense to me.

I finished out my work contract [at the Library of Congress], threw a bunch of stuff in storage, ditched my car in Ohio and flew into LaGuardia with two suitcases and a handful of couches to crash on. I’m basically the Peggy Sawyer of drag.

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So, were you always musical and theatrical?

Forever and always. I credit a lot of that to my mother, who taught me to sing at a very early age, and who was prone to put a Broadway soundtrack or movie in my Christmas stocking.

Prior to drag, did you audition for any shows or show work?

Yes, I did. Amidst small workshops or staged readings (which I still do from time to time), I spent some time off-Broadway in Showgirls: the Musical. It still remains one of my favorite projects. Talk about strong indications of being a drag queen!

Oh My God, who did you play? Please be the bitch who threw the pearls on stage to trip up that other bitch.

[Laughs] No, but that girl was fantastic. I played the redhead choreographer whom we named Gay Doubleentendre. I’m the kind of girl who loves the chance to chew the scenery, and that part let me have a three-course meal.

Hence, drag?

I spent a lot of time working for a bar where not only did the employees follow the queens of the city, they had two girls who were working on their own drag careers. Everyone would gab about the goings-on of the girls, and we would leaf through the magazines, and I would be stunned by the fabulous looks and lives they would live. After watching them and talking about them, I finally asked myself, “What kind of girl would I be?”

I decided that I would give it the old college try and really see what it took. With the help of several friends, I eventually debuted as my drag self onstage at Broadway Sessions. The rest, as they say, is herstory.

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Shirley has kind of a retro style, it seems. You shop at Enz! What’s your favorite fashion era that you call upon in your drag?

I look very much to the 30s and 40s. I grew up on a lot of old Hollywood as a child. So many movies with Danny Kaye, Rosemary Clooney, Shirley Temple, Vivian Leigh, Debbie Reynolds, and Shirley Jones formed so much of my humor and personality, that it only seemed natural to style myself after them.

And you wear a lot of cute hats, too! Do you have as many hats as you do wigs?

Why thank you! My hat collection has yet to surpass my wigs, but that certainly is a goal of mine. Because let’s face it, does anyone but a drag queen still wear a hat?

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You said recently that a person told you, when you were out of drag, that you were too cute to be a queen. Meaning, I guess, that drag queens are supposed to be unsexy clowns. I’m guessing this was an older person who told you this? I don’t think that the younger generation has that stigma about drag queens anymore.

It’s true, the gentleman in question was older than me. I think that this newer generation is paving the way for a more open and honest conversation about gender fluidity and non-conforming ideas about sexuality, which is a huge portion of drag.

However, I would be lying if I said that I haven’t gotten the same reactions from my own generation. Education, guidance, and exposure are all necessary to understand how all of these subjects intertwine, because no matter whether your implication is that a person is “too cute” to be in drag or you think a person is hiding themselves in makeup, the question is still inappropriate.

Sort of on that subject, I always wondered: a big part of traditional female drag is (duh) creating a feminine image. But when you sing in a male register, that kind of skewers that. So, when you sing in drag, are you more of a Singer then a Drag Queen in that moment? 

In many ways, I think the drag enhances a lot of what I’m singing. My baritone voice can make a song very funny, or the fact that I’m in a dress can make another song very sad or powerful. I think drag adds another subtle layer to what I do. Plus, a nice pair of sequin pumps is bound to jazz up any number.

True! What was your first drag gig in a gay venue?

Well, I did Sutton’s “Sing, Queen” competition back in the day at Barracuda, but my first non-competitive bar moment was actually in Rockbar. I competed against Petra Fried, and her co-host Hazel Tart was watching. We all automatically clicked, and they asked me to guest for their Wednesday night show.  It seems almost poetic that my first show becomes my return.

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The first time I saw you was Miss Barracuda this year. How was that experience for you?

Very eye-opening! I felt like it was a very important experience for me for a couple of reasons. For one, it pushed me way outside of my comfort zone. I was forced to rely very heavily on thinking outside the box, and it both terrified and excited me. I learned that my obscure creativity is worth pursuing.

In that same vein, it was worth pursuing because it showed me that not everyone will take to what I have to offer. A lot of times, the crowd was very polarized about my drag. Some were very vocal about it. I was very glad that Tina Burner believed in me to do it, because I I learned that no matter what people say, I have to nurture my creativity.

Your political video that you made for a competition challenge in that pageant was really cute. Was that fun to make?

It really was fun. Let alone how funny I think it is to make a video about how a drag isn’t mean enough for office, I had a ball running around Times Square shaking hands with unsuspecting strangers. You’d be surprised how many people either don’t want to shake your hand because you’re in a dress, or think they’re being polite by pretending you’re not to see you. “What man in a dress?”

Next came “New York’s Next Top Drag Queen,” a singing queen competition. What motivated you to enter that one?

I saw this as a competition that was right up my alley. I have always loved singing so much, and dreamed of singing next to a piano in a candlelit room. Additionally, I lost my job the week before, so I figured it was time to go big or go home!

That’s always the best motivator! Were you given your song categories in the beginning, so you knew all the music you’d sing throughout the whole competition? Or were you prompted week-by-week?

It was a week-to-week sort of deal. I almost like that better sometimes, because like you said, being under the gun is a great motivator.

Was hostess Holly Dae helpful and encouraging to the singers?

Oh, absolutely. She clearly had all of our best interests at heart, and loved to watch our creativity unfold. She’s such a joy to work with onstage.

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I watched a few of the videos of your performances from competition, including your lovely tribute to your dad using Gaga songs. Can you tell us about that?

Yes indeed. My dad was such a wonderful human being. He and my mom were high school sweethearts from Tennessee. He was highly intelligent, skilled, funny, clever. He was even leader of our Boy Scout troop.

In 2001, he caught pneumonia and died of secondary complications, leaving me and my two brothers to be raised by my mom. I would’ve been 13, and my brothers were 10 and 15. We struggled for many years, but we always had love in our hearts.

So very sorry for your loss. He would have been proud of you though, because you ultimately won the competition! 

I think he would have been proud, too. I think he would’ve been front row center for the finale.

How did that win feel?

It was such an amazing moment for me, to feel so validated in all of my hard work. They announced my name, and I was in such disbelief I couldn’t even respond.

Now, as part of your prize package for winning, you get to host your own cabaret showcase there at the Metropolitan Room, right? Do you have any details about that?

Nothing much more than the names of my director (Jay Falzone) and and music director (Michael James Roy), and that Nomi Sas will be joining me for a few numbers. However, I’m very much looking forward to working on a completely new piece, in a space I’m in love with, collaborating with people I adore. I’m shooting for a late September / early October performance date, and I will be constantly updating about every detail until the final night. Everyone should stay tuned!

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Can’t wait! Regardless, you’ll be returning to the Metropolitan Room to perform in Howard Ashman’s musical tribute, which features several other singers, on June 18th. Has Ashman’s music been especially meaningful to you?

I would say yes. I grew up on Disney music, and specifically remember watching The Little Mermaid a thousand times over. That Disney renaissance came right at the start of my grade school days. I’m so excited to be working on his lyrics, and building my own personal performance in his memory.

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And here’s exciting news: you’re first bi-weekly show! “Jest the Tip” debuts at Rockbar on June 7th. Rockbar is a good venue for singing queens: great acoustics! I assume you’ll be singing a lot in your show?

You bet I will! I pounce on any chance to do some singing, so I’m very thankful to Rockbar for this opportunity.

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What else can we expect for “Jest the Tip?” 

To watch a human Muppet in drag flail their arms uncontrollably.

 And also at Rockbar, later in the summer (July 16th), you’ll be part of Witti Repartee’s charity birthday show there. Do you know her well?

Yes, she and I are becoming quite the pair of bosom buddies. We met doing a staged reading of Die Mommie Die! and I’ve had such fun talking to her and learning from her.

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Any other upcoming plans or projects?

Well, I don’t want to say too much just yet because there’s still lots of planning to do. But I’m working on some new web content that I hope to drop later this summer. Keep your eyes peeled!

Okay, final question: If you were assigned to perform a one-woman show based on the life of any diva of the past or present–half campy, half serious–who would you choose?

Hands down, Mae West. What a funny, brassy, smart, self-assured woman in a male dominated culture. That’s a gal that I would love to do justice.

You’re off to a good start! Thanks, Shirley!


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Shirley U. Jest’s new show at Rockbar “Jest the Tip,” can be seen every two weeks at Rockbar beginning Tuesday, June 7th (6:30pm). She’ll perform for the Howard Ashman tribute at the Metropolitan Room on June 18th (4pm) and at Witti Repartee’s birthday fundraiser at Rockbar on July 16th (6pm). Shirley can be followed on Facebook, Instagram, Twitter and YouTube.

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