On Point With: Gem Annai

Here’s a live singing hostess on the come-up–we may be entering Pride Week, but it’s always Gem Annai Season!


Thotyssey: Hello Gem, Happy Pride Week! How is the season treating you so far?

Gem Annai: This Pride season has been busier than ever! But I definitely cannot complain; it’s been so much fun along the way.

Busy is best! Do you have all your Pride looks planned out, or are you living in the drag moment?

Honestly, I am living in the moment and taking one gig at a time, lol! Currently I’m working on two more looks before the end of Pride season, though.

So how long have you been a drag performer?

I’ve been performing in drag for roughly two and a half years, mainly within the Bushwick / Brooklyn scene, and some select brunches and events all over New York.

Can you describe to those not in the know what your drag is like today? For one thing, you’re a live singer, right?

Absolutely, I am a live singing drag queen who serves a stamped aesthetic, and is always giving new looks. I can also give a mean lip sync as well, so I definitely have a few tricks up my sleeve.

And this is an important question: are you actually a Gemini, lol?

Unfortunately no, I am a Scorpio… lol, just kidding! I love to joke about being a Gemini, because we tend to get such a bad rep from the other astrology signs. I’ve even had a friend truly believe I was a Scorpio, until they realized my name was a dead giveaway.

But yes, like a true Gemini I describe myself as a mirror to the other signs, quick-witted and agile, playing in the duality of the light and dark, and also playing multiple sides (devil’s advocate) in everything and balancing multiple perspectives–which could be why they say we’re all two-faced, lol! However, to know Gem is to love a truly cosmic experience that you can’t get elsewhere.

Can you tell us a bit about where you’re from, if you were always into some sort of performing, and how your drag journey began?

My family hails from the island of Puerto Rico; however, I was born and raised in Bushwick in the heart of Brooklyn, New York. I grew up very religious, and singing my whole life since the age of 7. I was a part of multiple school and church choirs, and eventually came into my queerness as a young adult.

I was first introduced to the art of drag and specifically RuPaul’s Drag Race by my best friend Norma Tears, who I co-host with weekly. One day while watching All-Stars 3, I turned to them and said “why don’t we try our hand at our own makeup?” Then I went to a beauty supply / drugstore and purchased a bunch of items, watched some YouTube tutorials, and thus was born.

We’re both perfectionists, so we practiced for a very long while before we ever stepped out in public–making sure we knew everything was polished (or as polished as a baby queen could be). Which brings us to 2021, where I showed up at Deep End’s karaoke in full Halloween Ursula galore, sang some songs, and was asked by the owner to host the next Drag Race Season 14. That was essentially the start of my drag career.

And you’ve been continuing to host Drag Race viewing parties, including the current All-Stars season! What do you think of it? Personally I don’t hate it, but I’m not loving it either. Too soon after a great Season 16, I think!

Absolutely. I usually love the All-Stars seasons, but this one is definitely a slow burn for me. I know this season is for charity and I really love the current cast of girls, but the non-elimination format sort of stripped away the higher stakes that are normally felt while watching All-Stars. A lot of the reasons we love Drag Race is the stiff competition and drama created throughout the season while girls are getting picked off one by one, making some of the most iconic moments in herstory. After following season 16, this has definitely been a sort of letdown as far as All-Stars goes.

Agreed entirely! But having said that… for the optimal All-Stars viewing experience, come watch Gem and Norma host it at the Deep End on Fridays, lol!

We will also be seeing you and Norma hosting some Pride events this week, starting Thursday in Chinatown.

Yes! We are hosting Peachy’s NYC’s first Pride-themed burlesque event on June 27th.

And then on Sunday aka Pride Proper, you’ll be at the Happiest Hour in the West Village!

I’m super excited for both events, especially since we don’t perform in the city as often! Norma and I performed last year at the Happiest Hour on Pride, and the energy from the crowd was insane. We basically gave a free concert to everyone, and they were all singing along and just exhibiting the pure happiness that Pride represents! Cant wait to be back for round two!

What else is coming up for you down the road?

I’m currently working on some music (like every other drag queen, lol) and some personalized merch to launch, as well as curating my own show at The Deep End.

All gorge! Okay, lastly: What is your favorite must-have item in your drag bag?

It would have to be my personalized rhinestoned fan. If you’ve seen Gem anywhere, you’ve definitely see that fan as well; I never leave the house without it. As a big girl, you never know how hot any venue can be… so it helps to have my own personal A/C, lol! As for cosmetics, it would have to be a solid black liquid eyeliner.

Thanks, Gem! Happy Pride!


Check Thotyssey’s calendar for Gem Annai’s upcoming appearances, and follow her on Instagram and Twitter.

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