On Point With: Jessie James

Boots & Saddle’s newest brunch queen is a quite the colorful crooner. Thotyssey goes on the run with Jessie James!


Thotyssey: Happy holidays, Jessie! So you’re in Boston right now… business or pleasure?

Jessie James: I needed a little vacay, and I’ve never been before! I went to Middlesex Lounge with my friend Levi, and we had a blast with Sham Payne, Vicki Powell, Wednesday Westwood, and all the others Boston queers!

Will you perform there at all?

Not this time around, but hopefully next time I’m back I can show Boston what’s up!

Well, you need the break – hosting a weekly drag bunch ain’t easy!

I don’t know about a break from hosting, but the concrete jungle in general, yes. This is my first time hosting my own show and it’s not easy, but I love it! There are so many drag performers in NYC, and some of them have multiple weekly shows – and some have multiple in a single day – all over the city. This is a challenge I’m more than willing to take on!

Where’s your hometown?

Deer Park, Long Island! I’ve lived in New York for 17 years, but I also used to live in Missouri and Florida.

You’re obviously a very Broadway-influenced performer… were you always into musical theater growing up?

Yes! I’ve done theater since I was 5 at my church in St. Charles, MO. Around the same time, I also shot my first commercial with GE. That’s how I got the performing bug! 

In middle school I got my first lead role in a play. and I continued all the way through college as well. While attending SUNY Purchase, I was fortunate enough to do a couple of shows with the White Plains Performing Arts Center. My favorite roles were Moritz in Spring Awakening, Bernstein in Dogfight, and Bud Frump in How To Succeed!

You were a veteran performer at a young age! Who were your Divas growing up?

Shania Twain! I know every song, every lyric! My family loves country music, so that’s what I grew up on. It wasn’t until later that I discovered really gay music, and becoming obsessed. My mom got a CD of an artist I wasn’t familiar with, and I listened to it on repeat on long car rides through Missouri. This was without knowing or caring who it was. Years later, I found out it was gay icon Cher this whole time.

Isn’t it always Cher?

It seems to always be her. Cher is like the shepherd for lost gay sheep!

So, did you discover drag when you came to New York City?

I moved to NYC in August of 2015, but I discovered drag when I went to SUNY Purchase. It’s a heavily queer-populated school. Everyone did drag, basically!

I also discovered RuPaul’s Drag Race then. I’ve heard there are Pride and Halloween Queens, but since Drag Race started I feel like there is a third type of queen, and that’s a Drag Race queen. If it weren’t for Drag Race, I’m not sure if I would’ve discovered it so quickly or would’ve been open to exploring drag for myself. 

Though some might roll their eyes at the generation of queens starting because Drag Race was basically dropped in their living room one day, but I feel that there should be the same amount of respect for the artists inspired through this wonderful show. I had the same thought as Bob the Drag Queen when she said once she saw her first episode of the show, she realized that she could do it and make it her own. 

Drag has helped me in almost every aspect of my life, but mostly mentally.

Let me tell ya, even though my family isn’t too happy with it, I have no regrets at all.

So your family hasn’t seen you perform?

No they haven’t, and I’m not sure if they ever will. My father (who is divorced from my mother) is about it though, and he’s from Mississippi. A common family trait of my mother’s side is stubbornness in our ways. I have come to terms with it, and understand that they’re only doing what they feel is right… so they can’t be blamed 100% for it. 

How did you drag name yourself, and create your persona?

Jessie J is one of my favorite singers! Also, I’m a fan of androgynous drag, so “Jessie” and “James” work. I didn’t realize until after I began using the name that there was a famous western bank robber and murderer named Jessie James! Though I used to watch the show years ago, I also didn’t realize that Team Rocket from Pokémon are Jessie and James. There’s a ton of references!

I have always pictured Jessie as the girl in high school who listened to rock and roll, though her parents never allowed her to. She was the girl who would skip class to smoke cigarettes behind her high school’s dumpster with her boyfriend.

Her personality was never a direct choice; it sort of developed the more I was in “Jessie” mode. We share traits, but where we differ is her confidence and directness. She speaks her mind, but with taste. Ironically, I feel as if Jessie has bigger balls than I do! 

And what were some of your introductory performances in the city?

When I started going out, I went to Industry on Thursday night and caught QUEEN! It’s a great show, and very consistent, which I appreciated. I met Monet X Change and after a few weeks, she invited me to do a number at her and Miz Cracker’s show at Hardware. It ended up landing on my birthday, and I sang “Sweet Transvestite.” When I say performed – I mean, I forgot almost every word. The audience chimed in to help out, and I got tipped pretty well! Everyone was so supportive, even though I was failing miserably! Monet gave me a little pep talk, and it gave me a good kick in the ass! So I guess I can publicly thank her for that!

I recall a performance of yours during the Miss Lady Liberty competition this year at the Ace Hotel: you were an all-green Elphaba, singing live. I bet that large scale performances with the vocals and the full looks must be a real treat for you to do when you can.

Oh, absolutely! I felt real pretty all green! I moved to NYC originally to pursue theater, so when I can pay homage to the work that’s shaped me, I LOVE IT!

Thank you, by the way, for participating in Thotyssey and Theater in the Now’s "Enough is Enough“ benefit for Gays Against Guns in October. 

It was my pleasure! What a great and important cause. Thank YOU for having the event!

Do you think drag queens should be more politically active in Trump’s America?

Oh, absolutely we should be more involved. We are a colorful group of people that are unapologetically and authentically ourselves. I’ve experienced people opening up emotionally and feeling free while around drag performers. With a superpower like that, we can change anything! 

In Trump’s America, we as gay people are in the back of a conservative’s mind for positive change and it seems like we are the target for restrictive laws. If we stay silent, we will be buried. We have gone too far and made too much progress to stop now. There is an America where we can all be equal, we just have to find it and build it for ourselves.

Okay, so now you are hosting the latest incarnation of Boots & Saddle’s Sunday drag brunch! 

Yes I am! I am having so much fun with the show! I had two trial runs before I started, and it really showed me that hosting a show is a lot more challenging than I anticipated. 

What are the joys and challenges of day drag?

The joys are being able to control the flow of the show, choose the material, and it’s just plain fun! I also have a different guest each week, so the show is never the same. A challenge is waking up at 8am to adequately give myself enough time to get ready. Another joy is already being in drag for the rest of my Sunday, so I could have a cute Sunday out!

And this Sunday in particular, you’ll be making your Boots Gurl debut for the 15th annual Toy For Tots Toy Drive, a great tradition there! That’s a very homey and Christmassy event, plus hot marines! Are you excited?

Yes I will be! I’m so excited! There’s going to be over 18 queens, and I’m proud to be one of them! I’m so stoked about the sexy-ass marines too! Some say that they love a man in uniform, but I love a man who’s uniform is on my bedroom floor!

It’s also a great event to help the less fortunate, which makes all of the tomfoolery feel a little more warm inside – but that also might be the whiskey.

Anything else to report?

As of right now, I will say that besides brunch on Sundays, I have no events that I can share right now… but keep an eye out on my Instagram! New and exciting things are coming!

Final question: How many times will you perform “All I Want for Christmas” this month?

Just about as many shows Mariah played after she canceled most of her Christmas tour this year.

Lol, thanks Jessie!


Jessie James hosts “Bitchin’ Brunch” at Boots & Saddle on Sundays (1pm). Check Thotyssey’s calendar for her full schedule of gigs, and follow Jessie on Facebook, Instagram and YouTube.

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