Maureen SanDiego Is Showing Chicago (And The World) Why Drag Is Just As Much A Woman’s World As It Is A Man’s

Drag, much like gender, is a construct best used when taken apart. Doing “drag” no longer means being a biological man in women’s clothing, and performing. Recently, drag kings, bearded queens, and bio queens have all taken to the stage across the nation and are putting their own individual stamp on what being a fierce drag performer truly means. Chicago darling Maureen SanDiego is one of the leading bio queens in the game today. This bawdy performer can turn a “lewk” with the best of them and her unique and refreshing performance perspective has her garnering fans and respect from Chicago legends like Lucy Stoole and T-Rex, among others. I sat down to talk with Maureen about how she got her start in the world of drag, her thoughts on a possible bio-queen season of RuPaul’s Drag Race and why there is definitely room in the world of drag for the ladies who want to take on this art form. 

Michael Cook: 

Right off the bat, when was Maureen SanDiego the character first born?

Maureen SanDiego: 
Maureen was the name of my 4th grade Catholic school teacher. She loathed my ass. One time she dragged me to the principal’s office for doing a Bill Clinton impersonation. You know the whole “I did not. Have. A sexual. Relationship. With that woman.” I was like nine years old and almost got suspended. I was just trying to be funny and ended up feeling so humiliated and ashamed, so I took her name. I didn’t even think twice, it just felt perfect. 

MC: What was it like performing for the first time on a drag bill?

MS: The first Drag showcase was in Chicago at “The Call” in 2015, it was Cher themed. I wrote a parody of “Believe” about Cher’s vampire-like immortality and then I did an eleven minute long lip sync of Cher performing the entirety of “West Side Story”. It wasn’t great; my entire tit accidentally fell out during the “Woman’s World” group finale. But I had so much fun! If there’s one thing you can count on when you book me for a drag show, its cracking jokes backstage. I just love drag queens so much and I’m always trying to impress them and make them laugh. 

MC: What kind of reaction do you get from the drag scene and the fans?

MS: When I first started I think people just thought I was batshit crazy, 2015 was a vastly different time. Once they caught my vibe and saw me perform, more and more people bought what I was selling. I’d already been doing comedy for two years and had a tough skin from that, so I knew I would just have to prove myself. The first couple of years I was extremely focused on producing new and exciting work. I just kept thinking “what can I do next, how can I be better than my last performance? How can I prove to my peers that I have a place in this scene?” I knew there was an audience for what I was doing.

The first time T-Rex tipped me, and I saw her laughing at my set, that was a really big deal to me. I also recall The Vixen throwing wads of money into a trashcan I was performing in for a competition at Berlin. That was fucking awesome. Gaining respect from entertainer’s I admired in Chicago meant everything. When it comes to fans, I think I have tunnel vision, I focus on the people who really love and appreciate what I do. But even if I have a killer set, I’ll still remember that one eye roll in the front row or shitty comment; I’m human. My persona is strong and unapologetic, but I’m a sensitive diva.


How would you describe your performance style for those that have never seen you live?

MS: I’m a self-deprecating and irreverent Cabaret queen. I write a lot about my life and Maureen can nonchalantly reference aspects of it that I’m often too ashamed or embarrassed to admit. My song parodies are usually about artistic poverty, suffering from clinical depression, pregnancy scares and weed. I’m a huge fan of musical comedy a la Bridget Everett or Varla Jean Merman. I like work that is outrageous and theatrical, but painfully honest. My last show was called A Star is Aborted and was inspired by a lot of the self-destructive divas and icons I admire. Celebrating and even brandishing your flaws like they’re a weapon. That’s where I tend to find humor.

MC:Bio drag is sometimes controversial to some women; what do you have to say to those people that still think drag is a man’s world?

MS: I had someone come up to me after a show recently and they asked if they could give me a hug because they always wanted to do drag, but didn’t think they were allowed because they were a woman. You’re one hundred percent allowed. Unfortunately, many people still associate drag with having a penis. I just associate it with being fucking fabulous. Drag, to me, is birthing an identity for yourself that you’re able to own and spurn art from. I know drag artists of all gender variants who are incredible writers, comedians, singers, cosplayers, jugglers, dancers, designers, acrobats, storytellers, seamstresses, directors, choreographers, playwrights… the list goes on and on. All the general public seems to care about is whether I have a penis? Isn’t that a little fucking tired? After all the work we put in to create a fantasy- that’s all you care about? Okay-then you better tip twenties.

MC: You are part of a growing group of ladies who are absolutely loving the art of drag; who are some of your favorites and why?

MS: You mean drag performers I love that aren’t men? Almost too many to name here!  Someone who I’ve always looked up to is Kat Sass. They killed it in Alaska Thunderfuck’s drag pageant this year and have pushed the art form forward in a way that has created opportunities for performers like myself. I also deeply admire Abhijeet and J for Pay for their work this year on The Chicago is A Drag Festival. The festival marked the 50th anniversary of the Stonewall riots with a lineup of 50 kings, queens and in-betweens. It was a moving and inclusive representation of what Chicago Drag is all about. Every performer on that lineup was awe inspiring and insanely entertaining. Oh and having a penis was definitely not a requirement.
(I mean, I was in it…)


Chicago has one of the biggest drag scenes in the nation. Who are some of the queens that you absolutely love and are a huge fan of?

MS: The scene wouldn’t be what it is now without T Rex. They area hilarious MC & host the biggest drag show in Chicago. T Rex set the precedent that everyone is welcome regardless of gender, orientation, favorite spice girl, etc. And they tower over everybody like big bird. Hard to miss that one. Then there’s Aunty Chan who helped usher in a new style of “viral drag” that has become standard for shows like Plot Twist and beyond. Lucy Stoole has a charisma and presence that is undeniable. I want her laugh as my ringtone. Then there’s Saltine who is a queen that writes her own comedic monologues which are indescribably bizarre and hilarious. She’s the Andy Kaufman of Chicago drag. And you can’t talk about Chicago Drag without giving props to The Vixen. Black Girl Magic has brought so many powerful queens of color to the forefront and its one of the most entertaining shows I’ve ever seen.

MC: If RuPaul’s Drag Race decided to do a bio drag season; would you do it? What do you think of the shows influence on the community?

MS: If RuPaul made it clear he wanted to be more inclusive in his casting choices across the board, I would consider it. But the cruelty of the online fandom scares me and doesn’t accurately reflect the drag culture that I’ve experienced. I’ve always felt more support and love than hate or cynicism in this community. RuPaul’s Drag Race is a business, a machine. Part of that competition is being asked to change wigs for the sake of changing wigs. And if you know me, you know I only own one wig. But yeah, I’m poor af so of course it’s tempting. RPDR made drag mainstream, it made drag something to aspire to. It also made millions of people who don’t do drag think they’re experts on the artform. It’s chaotic good.

MC: What inspires you as a performer and as a person?

MS: I pursue performance as a means of catharsis. My day to day life inspires me, walking to the bus, crying on the train, laughing with my friends, drunken stupors, bad sex, all of it. Making people laugh and escape and feel less alone through my art. That’s a higher calling to me. Astrology is cool too.

MC: What’s next for Maureen San Diego?

MS: Good question. I would love to travel more with my act. But mostly I’m just trying to make people laugh and pay my rent. I have a monthly variety show every 4th Wednesday at Berlin Niteclub called America’s Next Top So You Think You Can Impress Maureen Sandiego and I just came up with the title for my next cabaret, it’s going to be called Maureen SanDiego is Cancelled.



Photo Credits: 

Closeup: Jacob Bjorge

Garbage & Ramen photo: Joe Lewis

Weed: Erik Michael Kommer

Black: Jeff Ramone Photo

Pink: DS Shin