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Cara Connors’ swerving road to becoming a comedian

How being a “sassy, sassy little lady” helps Connors in the comedy scene
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U of T alum and comedian Cara Connors. COURTESY OF JASPER LEWIS
U of T alum and comedian Cara Connors. COURTESY OF JASPER LEWIS

U of T alum Cara Connors has been working the comedy scene since they graduated from The Second City comedy school’s Conservatory program in Toronto, following completion of a master’s degree at the Ontario Institute for Studies in Education. After publishing a piece on Connors’ most recent comedy show, The Varsity interviewed them about the journey they took to get where they are today.

In the interview, Connors made it clear they have always aimed to break down walls and show the world who they really are and who they want to be. Their strong mentality and bold personality shine through every set they perform — through their characters, physical comedy, and approach to more serious topics like gender identity. 

The Varsity: Why did you get into comedy? 

Cara Connors: I think I always consumed comedy and loved it, but I never really made the connection that it would be something that I would ever do or be interested in doing. I don’t know if I was blocking myself from my own happiness or if it just took me a minute to wake up to that, but I really never considered it until I started delving into it. After that first year of grad school, I started at Second City Toronto. I was like, “My people! I love this. Yes.” And then it all clicked and I had a Memento flashback of, “Oh, this completely makes sense.” It just took me a minute, you know?

TV: How did your North American tour go? What was your experience like?

CC: It was amazing. I’ve been doing comedy for almost seven years now, and I feel like I’ve been working my ass off the whole time. But in these last six months… it’s the hardest I’ve ever worked on something.

I think living in LA, there were these trade offs where I felt like I had lost my self agency a little bit. There’s not as much artistic freedom there. It’s like, you’re just doing a little shitty show on a Tuesday night at some crappy bar, but [stand-up comedian] Tig Notaro’s agent is in the audience. So the stakes are, all of a sudden, so much higher. A lot of people are telling you, “Make sure you’re always doing… your best five minutes, and you’re doing this and that,” and I don’t like people telling me what to do. Period, end of sentence. 

I think the tour was inspired by that. I wanted to take back my self agency and go out on the road — do it exactly how I want. I was like, “I don’t actually need any of you guys telling me anything. I’m just going to go and do this.” So that was the main inspiration: being a sassy, sassy, little lady.

TV: Do you think you’ve changed since becoming a comedian? 

CC: My whole life has changed since becoming a comedian. In almost every respect. When I started, I was straight, I was married to a man, I was going to become a teacher. And now, I’m queer and gender fluid, and I live with my Gen Z girlfriend. 

I think my personality has come out more. I’ve always been extroverted and always had that ‘class clown’ or mischievous element [in me]. I think when I first started stand-up [comedy], I tried to be more buttoned up. And now I’ve just been peeling all those layers back and just letting myself be myself. I just let those neuroses fly.

TV: Are there any milestones that you want to share?

CC: I remember it being a big deal doing my first show at a comedy bar. I won a Tuesday night local stand-up contest or something, and I got $20 Canadian, so I have [that] bill in a frame with the date on it. I always [regard] that as a touchstone [of my career]. And the milestones in between, [like after] my show in Austin, this couple… came up to me and they were like, “We drove three hours to see you.” And I was like, “Holy shit, someone even knows who I am.” Like, that’s a milestone. Someone that I don’t know has heard of me and wanted to come and see me. I’m so grateful; every person that follows me [and] every person that buys a ticket, I am extremely, extremely grateful for because I feel like I’m fighting for every little step up.