Cara Connors describes herself as a “former Catholic high school/current queer, corn-fed comedian.” That’s just part of the story. She started out in the Chicago suburbs, then moved to New York, Toronto and Los Angeles, all the while picking up experiences, insights, and brilliant comedic steam.
Cara grew up in Niles and attended Regina Dominican High School in Wilmette. College in New York followed, then marriage. Together with her husband, she moved to Canada where she made key discoveries that would change life for the better, both for her and for comedy fans.
It started with a chance walk by Second City in Toronto. Cara was in the midst of a desolate experience in grad school and needed something more. So she said goodbye to emptiness and signed up for improv. She divorced her husband and came out. Her career took off.
In just seven years, this effervescent comedian has become a headliner, actor, producer, writer, creator and on-screen star. Her feminist undercover investigative series Cara Takes Up Space is now streaming on OutTV. She describes it as “a mix of Nathan Fielder and Inside Amy”, though it is distinctly Cara. Her meaningful shenanigans would make Sacha Baron Cohen proud. She also stars on E!’s Dating #NoFilter.
Cara has performed at Montreal’s prestigious Just For Laugh’s Festival and had just appeared at the New York Comedy Festival’s Upright Citizens Brigade Headliner series when the pandemic hit. I asked her what the pandemic was like for her and she told me that “it was a fruitful time creatively” and “I don’t know if that makes me sound like a piece of shit!” It certainly does not! With more time and fewer obligations, she wrote a pilot. Not only that, she also watched all thirty-four seasons of 90 Day Fiance, spoofing it on Instagram and racking up nearly half a million views with her talent for impersonating voices and characters.
Cara is now on a fifteen-city tour taking her queer comedy showcase Straight for Pay on the road. The tour stops in hometown Chicago for one night only at The Hideout on Wednesday, March 2. With Cara that evening is Maggie Winters who was named one of Time Out Chicago’s Women of the Year in 2021. “Maggie,” Cara says, “is unbelievably hysterical and truly a star.”
Cara kindly spoke with me by phone about her singular journey, the power of queer comedy, the importance of being yourself, and in an equally delightful side note, our shared faith in Dog.
IN THE BEGINNING
Teme: What did you love or not love about growing up in Niles?
Cara: What’s not to love about Niles? The town motto has changed three times over the course of my life. It was “Where people count.” The one that always made me laugh was when they changed it to “Niles: it’s all here.” And it really is. I enjoyed growing up in Niles and being close-ish to the city. There were a lot of parks. I led a fairly feral childhood.
Teme: What is your most Niles memory?
Cara: Have you ever been to Booby’s? To me, it’s a very famous place. It’s a family-owned restaurant. They have these incredible steak sandwiches. I always think of food, but of course there’s the Leaning Tower. I felt very chic growing up with that. Obviously I didn’t get out much as a kid.
Teme: Which experiences most influenced your comedy?
Cara: I grew up in a big Irish Catholic family. Everyone’s loud and funny. You’d better be loud and funny if you want to keep up. It was like, “Oh, you think you’re funny? Well, my uncle is a snowplow driver, and he’s funnier than all of you, so shut the hell up!” I was sent to Regina as a punishment to try to straighten me out of it. I think that only emboldened me to be more of a loudmouth.
I would also say the Molly Shannon/Will Ferrell era of S.N.L. That cast had so many very physical female comedians and completely unhinged characters. I was always reenacting the Spartan cheerleaders and I memorized “Superstar.” I was constantly watching it on VHS.
HOW TO CONNECT
Teme: I noticed that you’re great at physical comedy, too. In one bit, you talk about feeling socially awkward and you reenact some of the things that socially awkward people do out in public. That’s me in real life!
Cara: I really wish I was exaggerating, so I’m glad that’s relatable. I’ve leaned into talking about those things instead of trying to put on some kind of facade. I’m talking about that in this [upcoming show], just coming out with it in the beginning and playing with the audience. I come out like, “I’m actually a really chill person.” But no, I’m literally having a nervous breakdown this entire set. And then trying to convince people I’m straight and coming out with that. So, yeah, the anxiety is definitely discussed at length.
Teme: How did you overcome it? Your depiction of anxiety is so on point, but you also seem very at home on stage and very natural and you connect so well with the audience.
Cara: Thank you. I feel like the more I lean into that part of myself, the more people actually connect with it. When I was starting out, I tried to cover it up. But it’s better to come out with the truth. I do feel very safe on stage. It’s this little protective bubble. I go on stage and the layers come off. I don’t know that I overcame it. I think I just gave myself permission to talk about it. It’s kind of a built-in safety net. If anything goes wrong … Not “if.” When something goes wrong or when some weird tech glitch happens or someone yells something or I trip over my words or fumble something that I shouldn’t, it’s already been named. So I can just be, “Well, here we go. I guess I can’t even say my own fucking set.”
Teme: I really relate. If I could go to a party and stand behind the curtains the whole time …
Cara: If there was a big dog behind the curtain as well-
Teme: Oh, perfect.
Cara: … then that would be truly ideal. Sometimes I just act like a four-year-old. Well, if my eyes are closed or I’m covering my face, no one can actually see me, right?
Teme: Exactly. And if I’m just talking to the dog, then no one can see me, either.
Cara: No one!
TO FIT IN OR NOT TO FIT IN
Teme: What does your comedy say about you?
Cara: My comedy says some of the things that I can’t necessarily say in my day to day life. I have, like everybody, these internal monologues and little neurotic things that I’m constantly worrying about. Comedy is a way for me to connect with people.
My comedy is pretty emotional and plays with a lot of moments of tension. That’s what’s been really fun about this hour. I have room to spread out. I don’t have to condense my identity and point of view into a three-minute set for twelve drunk people in a bar. Now I can actually get into it and trust that there’s a flow and that over the hour I’ll take people on a ride and they’ll want to come.
Teme: I think when comedians are honest that way, people both laugh and connect. It’s like therapy, spirituality and comedy all coming together in that experience.
Cara: Yes. I came up in the Toronto comedy scene. It was a very strong community. Then I came to L.A. and in many shows, it felt like there’s a lot of posturing, trying to play to the back of the room and inside references. My initial instinct was, I want people to like me and I want to fit in. And I won’t ever actually be able to do that. So I should just do the only thing I can. There is that Maria Bamford leaning into the mumbling-to-self and in and out of characters and leaving people wondering, okay, is she actually a little bit off kilter? Or is this a game? Playing with those things is always really fun.
CANADA AND TURNING POINTS
Teme: How did you end up in Canada?
Cara: I used to be married to a man, and we moved to Canada. It was right before the Trump era. We were both done with New York. I had gone to undergrad there. And he randomly suggested it. He was, “What about Canada?” And I was, “What about it?” We ended up there as kind of a progressive haven up north.
I was not doing comedy at all. Then, after a miserable first year of grad school I was feeling kind of lost. I saw that they had a Second City Toronto. I knew Second City from growing up in Chicago. My cousin used to be a Second City main-stager, and I would go and see her. So I took a class at Second City Toronto and that’s when I got hooked.
Teme: Back then, everyone said they were going to move to Canada, including us. Not a bad idea!
Cara: That’s the one actual tangible resource that I have. I don’t have any money or a 401k, but I do have dual citizenship. I feel like that might come in handy if some “Handmaid’s Tale” goes down.
Teme: To quote one of my best friends, you can’t have too many passports. What was it about comedy that spoke to you?
Cara: I always loved it. I watched every standup special that ever came out. In school, I was constantly being reprimanded and was the naughty class clown. But sometimes I think I’m a bit slow on the uptake with certain things. It takes me a minute to process, which is probably why I didn’t come out until I was twenty-six. I think it was the same with comedy.
I signed up for the class at Second City because I had such a miserable time at grad school and needed to do something fun for myself. I was on the streetcar after the second class. It was truly like an Oprah lightbulb moment. I was, holy shit! This is obvious. This is what I’ve always been meant to do. I had this flashback of all these things in my life. I was always making these little videos just for fun, but never showed them to anybody. It all just clicked into place.
Teme: Will there be more episodes of Cara Takes Up Space?
Cara: That’s my dream. I don’t know that there’s going to be more episodes because it isn’t in my control, unfortunately. I loved the social experiment side of it and was truly shocked by some of the things that people said to me. One episode we did, I was a bouncer. I got fired on the spot, kicked out and escorted off.
Teme: That’s awesome. I’d love to hear about that!
Cara: I went undercover as a man and got hired at this very douche-y nightclub in Toronto as a bouncer. Basically, I was just yelling at 18-year-old boys with fake IDs and lightly bullying them and trolling them for hours on end. But they let me check all the IDs independently, which was, quite frankly, their mistake. Apparently, I was asking inappropriate questions and asking for the code word or a trivia. And doing different accents. Just generally trying to upset and derail the night for a pack of 20-year-old guys in matching button-downs. The bar wasn’t happy. But yeah, that was fun.
Teme: May I ask you about your adorable dog? I’m such a dog person and I saw his photo on Instagram.
Cara: Oh my God. I’m sure you’re referring to Pepe a/k/a Pierre James.
Teme: That’s the cutest name!
Cara: He is the absolute best. He’s absolutely fabulous. He has definitely lived multiple lives. This is not his first journey here. I would gladly talk about him at any point. That’s the hardest part about going on tours. My girlfriend’s parents are watching him because they have two enormous basset hounds. Together they’re just this very, very funny crew. He comes with me to therapy. It’s very L.A.
Teme: I totally get all of that! How do you know he’s lived past lives? What kind of things does he do?
Cara: It’s just his energy. He has human eyes. Blanket statement: all dogs are amazing.
Cara: I love all dogs so much. But there are certain dogs that have that energy. He’s just so emotionally attuned. If I’m crying, Pepe puts one arm on me and, then he’ll look back at me, checking on me. He’s ten pounds, so he comes with us everywhere. He loves everyone and makes people happy constantly. He’s a secure man. That is the definition. He’s literally dismantling the patriarchy every day.
STRAIGHT FOR PAY ON TOUR
Teme: Of course I want to ask you about your tour and show! How did you decide to call it Straight for Pay?
Cara: “Straight for Pay” came out of an ongoing joke. My whole life, before I came out and before I knew that I was gay, I was acting straight and thought that I was straight, but was not comfortable in my own skin. There’s been this shift where now, in the last several years, I’ve figured out who I am and embraced that part of my identity.
But constantly, whenever we have any kind of queer story that’s being told, somehow 80% of the time, we’re still, “Gosh, let’s just give it to Charlize Theron.” So Straight for Pay is my campaign for myself and other people to steal straight roles from actual straight actors because I think that it’s time that we take it back.
It’s a nod to the fact that I do not want to be straight, and I’m glad that part of my life is over, but I will absolutely pretend to be so for a fat check. The joke being that I do still pass in many settings, which is very comical to me. I am hit on by men, which is always shocking and upsetting. And I still am called in for “young wife” and “young girl.” But I am gay for free, so that is important to know as well.
Teme: How did you create Straight for Pay?
Cara: I started it as a curated queer show. When I was in Toronto, I ran a weekly show. I loved hosting. That’s where I got my chops on stage and it forced me to write new things every week. I started the show in L.A. when I randomly met this guy at a show, and he said, “I have this yard. If you ever want to produce a show …”
At first I was, okay, this guy’s going to murder me. So I sent my location [to friends], and went and met with him. It turns out he has this beautiful yard, and he just randomly liked me after a show.
So I started asking my favorite comedians in town. Probably 90% of each lineup is queer. Many comedy shows and especially comedy clubs, if there’s one female headliner a month, it’s “Wow, they’re really doing well.” If there’s two women on the lineup, one’s going to go up second, and one’s going to go second-to-last because “obviously, two women back to back are going to say the exact same thing.” But fifteen men in a row talking about jerking off, that’s okay. We’ve never heard that story before!
When the clubs started opening after the pandemic, it seemed like every club in L.A. was eager to welcome back Louis C.K. or Chris D’Elia. What the hell is going on? So, not to be avant garde, but I wanted to have a show where people on the lineup haven’t all been accused of sexual assault. So that was definitely a big motivation.
I want to take this hour and eventually make it into an album called Straight for Pay. I’ve worked out a new thirty to forty minutes in the last six months at the showcase. The hour now is a hybrid of the New York Comedy Festival hour plus the new half hour, and going through my own weird process to figure out my favorite sixty minutes.
Teme: Do you have a favorite story from the tour so far?
Cara: I did my show in Denver at a club that has a house dog. They have a pug. There was this group of people that were super excited and super cute and just glad to be there. But everything that I was saying, they were responding to and then chatting about. I had to do a, “Look, I can see I’m going to have to use a firm hand with you guys.” And then they liked that even more. It had the opposite effect. I finally got them to calm down. Explained to them what a show is and how to sit and not talk.
As soon as I got them settled, I start the next bit, and turned away. And that’s the moment that the pug chose to walk into the audience. Then of course, everyone loses it, myself included. And I was, “Okay, we have to take a second. Let’s talk about this dog. It’s incredible.” So I’m just as bad as them. I have ADHD and I’d got myself back on track and then completely get derailed because there’s a pug. But what do you expect?
Teme: A pug! What can you do?
Cara: What I wanted to do was put his sweet little bed on stage. But we already started thirty minutes late. There was a blizzard. I was, okay, not today. His name was Mochi. He was in a little flower sweater. So, so fat. You could audibly hear every breath. It was incredible.
Teme: Do you have anything that you’re always sure to bring on tour?
Cara: I do. I have a crystal that my best friend gave me. I also have a childhood photo – I did an inner child healing with my therapist – where I’m painting and there’s kids in my class around me. They all are painting these rainbow finger paintings, and mine is just all black. So it’s just a little reminder, like: “Yeah! Be yourself!” And be kind to yourself. Those are my two little talismans.
Teme: What was the most recent thing that made you laugh?
Cara: My girlfriend makes me laugh constantly. But my most recent laugh … We just got to Austin (Texas) and we went to a place that’s a coffee shop/brewery/dog park. We went in and sat down and there was this humongous dog next to me. I’m going to sound like a crazy dog lady in this article.
Teme: Same here!
Cara: What made me laugh was there was a huge sleeping dog under a table where a guy was sitting. Then this woman approached the guy and said, “Oh hi, are you Kevin?” And he stood up right away. Then the dog immediately stood up and bumped his head on the table. It was so awkward. At first I thought it was a first date, but it was some kind of work consult. But clearly, the guy and the dog were not expecting this woman who walked in to be extremely gorgeous. And I was, wow, that would be me, smashing my head as I’m trying to look cool at the same time.
WEDNESDAY NIGHT AT THE HIDEOUT!
Teme: Absolutely anything else we should include about the show!
Cara: I’m very excited to do a hometown show and to perform for friends and people that I went to high school with who maybe didn’t like me very much, but now they maybe will be nicer to me.
I mentioned my cousin is a Second City person. She’s ten years older. I always had this very nerdy fixation on her and was constantly the equivalent of tugging on the end of her jacket trying to get her attention. I always joked with friends, “I’ll know that I made it when Carisa comes to my show.” And now she has said that she’s going to be coming to the show.
I definitely want to make my hometown proud. I’m going to have a lot of friends coming out and people who have had my back from day one. I want to make them and my cousin Carisa proud.
Cara Connors’ Straight For Pay Tour comes to The Hideout, 1354 W. Wabansia, Chicago, on Wednesday, March 2, 2022 at 9:30 p.m. With Maggie Winters. TICKETS HERE.
If you’re not in Chicago, find Cara’s tour here.