On Point With: Holly Wood

This Toolbox temptress is about to serve us all the cakes… cupcakes, that is. Everybody comes to Holly Wood!

Thotyssey: Hello, Holly! How are you enjoying April so far?

Holly Wood: Thank you! April has been fabulous so far; I live for the heat! I have also had some really exciting gigs this month–it’s been really nice staying busy.

No doubt! Please tell us a bit about where you’re from, what you’re creative interests have been, and how you came into the world of drag.

Funny enough, I’m not from Hollywood–or anywhere even remotely close, lol. I grew up in Westchester, NY! I have always been passionate about performing for as long as I remember. I’ve been doing musical theatre since I was in the 4th grade, and I was always really frustrated that I never got the “leading man” roles because I’m super femme; they always cast me as a featured dancer. When I went to college for theatre I said “fuck it” and started auditioning for the female roles that fit me better. That’s when I got really interested in performing in drag, but I wasn’t necessarily ready to be a full queen yet.

I’ve always loved women’s fashion and makeup as well, so it didn’t take long for me to start buying women’s clothes and experimenting with makeup looks. I remember when I got my first lace front wig and felt the full Holly Wood fantasy for the first time. I felt so gorgeous. It has been full throttle since then! Once you put on drag, it’s hard to stop.

How would you describe Holly as a queen today?

Holly Wood is the Elle Woods of drag! She’s always blonde, and usually wearing pink. I’m super inspired by all the dumb blondes that came before me – Romy and Michele, Shelley from The House Bunny, Glinda, Karen from Mean Girls… I feel like an amalgamation of all of them. I also am a huge Lady Gaga and Madonna fan, so I am always doing a number from one of their discographies… or dressing in Gaga / Madonna drag. I cannot forget to mention Marilyn Monroe, too; I dream of being as glamorous as her. My favorite number to perform is probably “California Girls”–it’s a fan favorite for sure. I love numbers that get the crowd singing along and dancing with me.

And how did you ultimately become a Toolbox queen?

I was a regular at The Toolbox before working there. It’s truly my favorite bar; it was my safe haven when I moved to the city, and I have met so many amazing people by being a regular there. I started showing up in drag from time to time, and they asked me if I wanted to do a number one night. After my performance, they gave me the Wednesday slot… and I’ve been there for a little over a year now. I love it!

What are the Toolbox Wednesday trivia / game nights that you host like?

I would have to say my favorite moments as a queen are always when I am hosting my Bachelor Gameshow there. Every Wednesday at The Toolbox is trivia night, and the Bachelor Game has definitely become a highlight of the night! I have a sexy guy come on stage, and the audience has to guess his sexual preferences (top, vers or bottom, favorite kink, etc). It gets pretty hot! I love seeing the reactions of the audience when they discover the bachelor’s dirty secrets. It makes my job so much fun, I love revealing how slutty people can be!

And you have another gig coming that looks fun, April 30 at Slate NY: “Cupcakes & Cocktails!” Your fellow Toolbox girl Phoebe Jeebies will be hosting that, and the lovely Vanity LaVain will be there, too. It looks likes you’ll be doing shows and showing us how to make drinks and cupcakes! Tell us a bit about how this came about, and what we can expect.

It’s something that Phoebe came up with! She started baking in drag during the pandemic, and it turned into a new show. I went to one of her previous baking shows, and had an absolute blast. I love Phoebe so much; she’s been a big sister to me, and I am extremely grateful she asked me to be a guest. Plus, I cannot wait to work with Vanity as well–she is so stunning. A bunch of my family that hasn’t seen me perform in drag yet is going to be at “Cupcakes & Cocktails,” so the pressure is on!

What are your go-to cupcakes and cocktails, by the way?

Ooooh! I love a good funfetti cupcake with vanilla icing, and sprinkles of course! The gayest type of cupcake. I’ll wash my cupcake down with a cosmo.

Delicious! Let’s close with some words about the show: Drag Race Season 15! Were you remotely surprised by the end result, and were you satisfied with the season overall?

Not surprised in the slightest! My friends and I were doing a fantasy league all season long, and it was an absolute blast. It made the season even more fun to watch. I was Team Mistress for the win, but I’m sure that we will get her back on our TV screen soon enough! I am so beyond excited to see what Sasha Colby can do with her reign. She is truly a superstar.

And as your name suggests, you’re a superstar in the making! Thanks, Holly!