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Interview: Dixie Lynn Cartwright, the drag queen who always wins

Written by
Adam Guerino

Dixie Lynn Cartwright is all about supporting the arts. In her monthly show, Dixie Wins A Talent Show, she encourages contestants to compete for second and third place. That’s right, as the name would indicate, Dixie always wins. As a popular drag queen, talented singer and in-demand MC, one might worry that it can go to your head. Well, she went the other way and unapologetically embraced it all. Dixie Wins A Talent Show welcomes multiple contestants every month from drag to singing and comedy. The performers are top-notch and, though you might think the appeal is the second and third place cash prizes, the real fun in the show is being able to share the spotlight. To talk about the show, I got a chance to talk to the man behind the big blond Dixie wig, Drew.

You've mentioned before that talent shows hold a special place for you. Have you participated in many and what did they mean to you?

I am mesmerized by middle school talent shows. They are always a pre-teen trainwreck. Pre-teens in general are a trainwreck, but this one happens on a front of other pre-teens. It’s intense. When I was in 8th grade, I won the talent show with a stirring rendition of “Climb Ev’ry Mountain.” I was a 13-year-old boy with a bowl cut, a Snoopy Around the World tie and a dream. It was in a gymnasium. It was hot. The silver spray-painted cardboard letters spelling out "TALENT SHOW" kept falling off of the velvet curtain. It was, in a word, magic. I hope that my grown-up talent show can bring the same pre-teen trainwreck magic to the people of Chicago who don’t have to be up early on Thursday.

Some people think of you as a singer or a drag queen but I just think of you as a megalomaniac. What's it like being a triple threat?

Yes. I agree. I am incredible.

Wait, I answered that wrong, didn’t I? It’s fun being all the threats. It presents its own challenges because people don’t know how to take a live-singing drag queen who makes terrible jokes. It’s too much for one beautiful person...but I do it. I feel like it takes a minute for an audience to get into me, but I’ve got time. I’ll wait.

Which came first, singing or drag?

I was Tennessee’s least-successful drag toddler, so I hung up my bedazzled Keds and focused on singing for a while. I sang a lot growing up. I did show choir in both high school and college because long, gangly white kids should absolutely dance to “Walking On Sunshine” in a sequin vest. I kept waiting for my singing voice to drop. It did, to a degree, but I still had this crazy high lady register. I joined the Chicago Gay Men’s Chorus when I moved to Chicago to meet people (i.e. find a husband). They have an annual live-singing drag show called Lipstick & Lyrics. I was too terrified to audition, so I drunkenly showed interest at a party after I heard someone dropped out the last minute. I did the show, loved it, but was also so afraid my parents would see pictures on Facebook. A lot has changed. My mom has actually come to see me in drag. I think she’s glad that at least one of her kids is pretty now.

Where did your drag name and persona come from?

When I would speak in public, I would become so nervous that my Southern accent would assault the audience. So, I knew it had to be a Southern name. I love Dixie Carter from “Designing Women” because I’m a stereotype. I wanted three names because that’s incredibly Southern, so I chose Lynn, my mother’s middle name. I tacked “right” onto the end because I’m always right. I don’t really get nervous when I speak in public anymore, so the accent isn’t as thick, but drinking helps bring it back…so I drink a lot. Dixie’s persona is dry, charmingly bitchy, and self-deprecating. I think those are three qualities that I love about Drew, but look better on Dixie. Self-deprecating humor works well with fake eyelashes and press-ons.

What can people expect from the show on June 3?

This show is going to be amazingly dumb. I can’t wait. I have two powerhouse female singers, Erin Daly (an incredibly busy working actress/singer) and another special guest. They will make you angry at your parents for not birthing a more talented child. I have a stand-up comedian, Joseph William Reese, which we haven’t done before, but I’m excited for the change of pace. I like jokes. We also have three drag queens, who all bring their own style to the competition. Tequila Mockingbird is a stupid-good singer and kooky personality, Fox E. Kim has made a name for herself in the geek/comic world and Betti Kyle is fairly new on the scene which makes her unjaded and not dead inside. We also have past winner, the amazingly talented singer/dancer drag queen Alexis Bevels, returning to perform between the two rounds. She’s too good to be allowed back to compete. And of course, our winner is crazy talented. She’s just so good. So pretty, so talented, so funny, so skinny—you get where I’m going with this. 

If someone wanted to lose to you… I mean, compete in the talent show… how would they submit an entry?

Email me at or contact me via Facebook. I'd love to have all different kinds of acts! Just send me a blurb about what you do and where I can find a video of it. Thanks, bros.

You can see Dixie and her humility at Dixie Wins A Talent Show every first Wednesday of the month at Berlin Nightclub 954 W Belmont starting at 9 pm.

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