Not long after their first 15 North American shows, stand-up comedian Cara Connors will return to the stage on June 9 at The White Bull Tavern in Boston’s Faneuil Hall for the second leg of their tour, Straight for Pay.
“It’s an examination of my own coming out and ‘coming to Jesus’ moment of realizing I’m homosexual, and deconstructing gender in our lovely political climate that we have right now,” Connors said of their show.
The comedy writer and actor embarked on their journey seven years ago after realizing graduate school wasn’t for them. While many of their peers chose a more “traditional” path, they took a detour and put their own dreams ahead of the societal norm. After having an interest in comedy their whole life, starting stand-up made everything make sense for Connors.
“Like many millennials, I went [to college] because I had no idea of what I wanted to do, then at a desperation point, decided to finally do something fun for myself,” Connors said. “Stand-up specifically I’m drawn to because you have complete control over everything, like the energy you’re putting out, what the narrative is, and what kinds of things you want to speak about.”
Connors lives for the rush of live performances, fueled from the energy exchanges with their audiences. They are able to let go of the complexities of everyday life once they step foot onto the stage.
“When I’m actually performing, I’m fully present and in the moment,” Connors said. “It’s when I’m the happiest, it’s when I’m fully immersed in what I actually enjoy doing.”
Connors’ career has been a work in progress as their comedic voice becomes clearer. Rather than separating who they are as a person and who they are as a comedian, Connors chose to merge the two identities as they became more comfortable with their craft, allowing them to be themselves.
The queer comic takes much pride in their sexuality, saying this part of themselves “colors everything.” Performing stand-up brings out raw vulnerability for Connors—something that can be hard for many.
“My personality in my comedy has only begun taking up more and more space, and [I] get the best reactions when I actually am myself and reveal that on stage,” Connors said. “[My sexuality] definitely plays out in terms of the material I’m tackling right now. I don’t necessarily want to be political all the time, but it seems like certain people existing is political, so I feel like I need to speak up about it.”
Just as Connors grows as a person, their creative process evolves with them. Like many, Connors’ Notes app is filled with lists and important ideas—it’s a spot for their many tabs on things that annoy them, inspire them, or were said to them. From there, they write and draw out their ideas which are used as a jumping point to fuel their comedic expression.
The next step comes with an open mic, which they describe as a “horrifically painful experience,” dishing out fresh content to people who can’t be bothered to pay attention. Despite the difficulty, it’s a necessary part of growth.
Working on a chunk of 15-minute long material at a time, Connors builds from stepping stones until an hour-long show like Straight to Pay comes alive—a show that’s taken several years to construct. Just as the stage feels solid beneath them, the comedian needs the same effect for their writing.
“You have to do things that are established, then sneak in a new thing to see if it works, and move it to a different spot and just keep rotating it,” Connors said. “Now that I’ll have more time on stage at my own shows, I’ll try to work in stuff, like maybe five minutes of new material I’ll perform and just build it that way.”
In order to get their footing and flourish in the comedic industry during the first part of their tour, Connors initially chose 15 progressive cities they personally had a connection with—whether they went to school there, performed previously, or had friends in those locations. Throughout, their adrenaline was skyrocketing as they experienced various communities of comedy, queerness, and city life.
“Overall, it went really well and it feels like there’s some momentum building off of it as people tell their friends,” Connors said. “[Spreading the word is] very much like a DIY marketing type of thing.”
After experiencing loving audiences and successful turnouts during the first half of the tour, Connors is eager to get back on the road. This time, they’ll be exploring much more than nationwide cities as they branch out into Europe for several of the 15 upcoming shows. With more back to back dates, Connors is preparing by researching and learning about the new places and their audiences—Boston included.
Without the comfortability of knowing these places and having personal connections to them, Connors is faced with a challenge—one they welcome.
“Even one city can vary by the time of the show, the venue, who comes out, and just the mood people are in and what the moon is doing,” Connors said. “I don’t know what British people think is funny, they might be like ‘what was that?’ But that is exciting to me, just to be on my feet a little bit and respond to what people are doing.”
Though Connors wishes there were programs like Emerson’s Comedic Arts during their college years and start in Toronto, they’re delighted for the future generations of comedy. Connors urged those studying comedy, to collaborate with everyone and anyone they deem funny. Particularly during these formative years, any project is important, allowing a space to practice and grow with one another.
“Even if you don’t know them well, take the risk to ask them to make something or write a sketch and film it, make a TikTok, make a small thing,” Connors said. “The collaborative aspect…is what made me feel really supported…When you’re in it and still learning how to cut your teeth, those are the people that are going to get it more than anyone else.”
Connors used their personal experience from lasting relationships made when they were just starting out. They emphasized being fearless and following one’s genuine dream of doing comedy. Connors said it’s this drive that keeps creatives going, and that failing should not be a thought that stops them.
“Take any opportunity,” Connors said. “There’s no failing. Failing is people that are too scared to even get up on stage. If you’re going to fail, fail big and take chances to do stuff. That’s what it is if you want to be an artist.”
