When you meet Wes Perry for the first time, you know you are in the presence of fierceness. This Tuesday evening, while battling a stomach flu, I met up with Perry for drinks and loaded tater tots at Mary’s Attic in Andersonville, and I was immediately struck by his larger than life stature.

Cloaked in an oversized coat and his signature beard, Wes Perry left the blue lipstick at home yet brought the wit, charm and delicate humility that’s a signature of the Perry brand. I’ve never been lucky enough to Making Out with Wes Perry and Friends, his monthly show at the Upstairs Gallery, but I know Perry through his immense reputation in the Chicago performance scene. In addition to a glowing review in this month’s Huffington Post, who described Perry’s show as a microcosm of everything they love about Chicago, Time Out Chicago has described his work as “show-stopping” and Windy City Times called Don’t Act Like A Girl “a journey of great comic timing and reflection.”

This Sunday, I’ll be able to attend Making Out with Wes Perry for the first time, as Perry brings the show to The Hideout on Sunday. In bringing the party to a new space — for one night only — I asked Perry to take me on that journey with him.

Nico Lang: Before you started “Making Out with Wes Perry,” you had your own one-man show, Don’t Act Like a Girl, at the Annoyance. How did this event evolve out of your own performing work?

Wes Perry: Don’t Act Like A Girl was my coming of age story, it mixed my own storytelling with song covers I did with a live band. We used a variety of music, ranging from jazz standards like “The Man I Love” to Ozzy Osbourne’s “Crazy Train”, a friend of mine said the show was like a mixed tape. The music was integrated with the stories, so these popular songs became part just another way for me to tell my own stories. When that show was over, I wanted a space where I could continue to perform this way, and that’s when I started Making Out.

NL: As someone who has never had the chance to attend, what should I expect from this Sunday’s performance? I’d love a preview of things to come.

WP: Improvisers, dancers, musicians, storytellers, and performance artists would be the short answer. The long answer would be some amazingly innovate artists, who  would normally be found spread out all over the city; in fact they’re people I have traveled all over the city to see! It will be an insane range of performers, all of which I think are incredibly powerful, original, and funny. I’ll be there to bring everything together, telling stories and singing songs backed by a four piece band.

NL: “Making Out with Wes Perry” usually takes place at Upstairs Gallery in Andersonville, a space that you’ve said is very crucial to the ambience of the evening. You’ve described the space as being like “your gay uncle’s living room.” This will be your first time putting it on at the Hideout, which is considerably larger. What made you want to start experimenting with different venues?

WP: They are two of my favorite places in Chicago, both buildings just have an energy that says “stay awhile, this will be fun!” I also love the flexibility of both spaces. I wanted to try something new mainly because we are constantly sold out at Upstairs. So we’re trying something new, new venue, new night, new part of town. I first went to the Hideout when my friend Seth Dodson, who is performing in the show Sunday, had his wedding reception there, and I’ve been in love with it’s cozy wood-paneled clubhouse feeling ever sense. Plus any venue that has hosted Chances Dances, Fred Armisen, and Mavis Staples is clearly a place where magic happens.

NL: “Making Out” is one of a number of exciting performance nights in Chicago, including Northern Lights, Salonathon and All the Writers I Know. What do you see as your relationship to the queer performance scene in Chicago and these other events?

WP: I love Northern Lights and Salonathon, they are two communities I feel at home at and they have helped shape me and this show. There are also so many alternative comedy shows and venues that I am or have been a part of, The Annoyance, Kill All Comedy and many other shows at the Upstairs Gallery. These are just a few of the places where I’ve performed myself, and where I’ve met people who’ve been in Making Out. I think all of those shows, events, and theaters are amazing creative spaces that I’ve been so lucky to be near, and now I’m somewhere in the middle, trying to bring them all together, mixing both the performers and audiences.

NL: As a performer, you often blur the lines of gender. Special attention is given to your choice of lipstick, often of the blue and sparkly variety. What do you hope that your own gender performance says? What are you trying to get across?

WP: My glittery lipstick has kind of become this trademark. I used the effect in Don’t Act Like A Girl, and then I started wearing it out to bars. It always puts a huge smile on people’s faces. I’m lucky enough to have this space to perform whatever I want, so I made an active choice to dress that way too. I’m often in button down shirts and leggings, like a 6’4” Elaine Stritch with a beard. I don’t think the way I look is revolutionary, but I think seeing someone dressing and behaving however they please can be a powerful sight, especially when you’re the largest person in the room, literally.

NL: What’s unique about “Making Out” is how the night brings alternative, straight and queer performers together in a night that blends different communities. Why was that important for you in curating this event?

WP: As a creative person you often find a supportive like minded community, and Chicago is full of them. These communities support their members and encourage working together, and the only downside is that sometimes people get caught up in their comfort zone and they forget to step out, or maybe they don’t know where to step. I try to make it easy for people, they just have to make one step, and hopefully they’ll be transported by works that have been born and nourished all over the city, but for just one night are all under one roof.

NL: Considering that this is a mixed space, what kinds of reactions do you see from folks who are exposed to different styles and identities?

WP: I think only good things can come of variety, which the show has both on and off stage. Every performer is someone I’ve been inspired by in some way, and I’m just hoping to pass along the inspiration to both the audience and the other performers.

NL: Your background is in theatre and improvisation, as a student at Columbia and a long-time performer at the Annoyance, experiences that have shaped your perception of community. You describe Chicago as an “ensemble city.” What do you mean to signify by using that phrase?

WP: Chicago’s best performance venues are based in ensemble work, Steppenwolf, Second City, The Neo Futurists, The Annoyance, The Hypocrites, the list goes on and on. It’s something that’s in the blood of the city,  something they instilled in me at Columbia from the first day, and something I experienced first hand training and performing at places like iO, The Annoyance, and the Second City Comedy Studies Program. Support is second nature in this city, and I’ve been so lucky to benefit from a lot of great support.

NL: As “Making Out” continues to grow, you’ve mentioned continuing to experiment with the format, such as having a weekly interview show over the summer. How do you hope to see the show evolve?

WP: We have a lot of ideas bouncing around, like doing a weekly version where performers are interviewed like a talk show, putting up a “Best Of” showcase, or even doing a filmed version for online, but we’re going to see how Sunday goes first. Whatever happens we’ll try to do it slowly and carefully, I’m not in a rush to mess with anyone’s “church.”

You can catch Making Out with Wes Perry and Friends this Sunday at The Hideout in Bucktown (on 1354 W Wabansia Ave.) Doors open at 7 and the show commences at 8 p.m. sharp. You can also see the show as usual every month at Upstairs Gallery in Andersonville.