Comedian Kyle Shire Answers Our 10 Questions About Chicago

"When it comes to meeting sexy locals, I don't care for pretenses. Hence why I like the dark, seedy, kinda pervy places...."

On January 17, subscription-based gay entertainment service Dekkoo, launches its new, six-episode Out on Stage: The Series, featuring a diverse line-up of 16 queer comics hosted by Zach Noe Towers.

One of the comics featured in the series is 28 year-old Kyle Shire. At 6’5″, the Chicago native is a larger-than-life performer (both physically and stylistically) known for a loud, irreverent, rant-based comedy fueled by high-energy nerd rage. Prior to the his appearance in the series, Shire created and hosted Cobra Juice at the Steve Allen Theater in Los Angeles and is an in-house producer/host for Machinima, contributing on shows like Body Count Fight, Action Figure Comics, and VR Power Hour.

Planning a trip to Chicago? Here’s the funnyman’s take on where to go and what to do when you get there:

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1. What is the best thing about Chicago?

It’s hard to pick just one best thing about Chicago, but if I had to shine a spotlight on one thing, it would be that Chicago has some of the best architecture in the country. The buildings are more than just gorgeous, they tell stories. My favorite building in the skyline is the Carbide and Carbon building, which was designed to look like a giant champagne bottle, supposedly serving as a giant “F-you!” to the prohibition era.

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2. What is your favorite tourist attraction?

The Art Institute of Chicago. It’s situated to provide a perfect afternoon. You can live your Ferris Bueller fantasy looking at A Sunday Afternoon on La Grande Jatte, and then meander through Grant or Millennium Park, or explore the Magnificent Mile, or fill your gullet with delicious Garrett’s Popcorn. In the winter they have ice skating just up the street. It’s super close to the Loop, so you can just hop on a train and go anywhere afterward. You can plan and do so much in a single day.

3. And, the most overrated?

Navy Pier. Don’t get me wrong, the Ferris wheel does give you a gorgeous view of the city. But it’s way too expensive, and parking and public transit are inconvenient. Unless you’re there for a convention or something, you simply just don’t get a good return on the time and money you invest in exploring Navy Pier.

4. What one thing should every LGBTQ tourist make a point to see/do/experience in Chicago?

Chicago has some of the best live theater in the country, and it has a wide variety of it: The Chicago Theater, The Goodman, the Oriental, Briar Street Theater, iO, Zanies, and Second City. Whether you’re super into musicals (not me), raunchy stand up (more my style), or weird experimental theater where the actors are dressed like ladybugs and force you to eat cake out of a top hat with your bare hands (actual experience I had once), you can find some live theater you’ll be into.

5. Where is the best place to meet sexy locals?

When it comes to meeting sexy locals, I don’t care for pretenses. Hence why I like the dark, seedy, kinda pervy places like Jackhammer. Going to a bar is just an elaborate mating ritual, whether your gay or straight. Why run from that fact when you could embrace it in a pitch black room, packed with sweaty strangers? Small talk is overrated.

6. Where is the best place to grab brunch?

My absolute favorite place to food at any time of day is The Pick Me Up Cafe on Clark. I’ve been going there since I was a junior in high school. It’s open 24 hours. The atmosphere is warm and cozy, the food is spectacular, the service is always very down to earth and always willing to let you just relax and chat for hours. Also, it is at the tail end of Wrigleyville, so if you’re there around 2:30am you can watch all the drunk heterosexual messes shambling out of John Barleycorn. It’s like a zombie movie sponsored by American Eagle. It’s the best.

7. Where is the best place to get a cocktail?

I’m not a big drinker, but I am a gigantic nerd who loves an occasional bourbon, so I love checking out Replay on North Halsted. It’s full of retro arcade cabinets and their bourbon selection is tops.

8. Best place to catch queer comedy?

Last time I was back home I saw a wonderful queer comedy/variety show called The Kiki in Andersonville. Highly recommend you check it out.

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9. And the best neighborhood to spend an afternoon?

Boystown gets a lot of attention, but Andersonville is growing to be just as gay and just as lovely. You should give that part of town some love.

10. Who or what is everyone in Chicago talking about right now?

Are those Mothman sightings real? Answer: probably.

Bryan van Gorder usually writes about the places he's been or the famous people forced to talk to him.