Kay Cannon set out to make people laugh onstage doing improv and sketch, but when Tina Fey asked her to join the writers’ room of “30 Rock” back in 2006, she did what any sane actor would do - she said, “Are you kidding me, Tina? Absofuckinglutely!” Okay, I don’t know if those were her exact words, I didn’t ask. But let’s go with it all the same. Nearly twenty years later, Kay has racked up an epic amount of TV experience (including “Girlboss”, a series she created), wrote all three Pitch Perfect (2012 to 17), and wrote and/or directed three more feature films (Blockers (2018) as director, Let It Snow (2019) as writer, and Cinderella (2021) as both). Her work is notable for being hilarious, charming, and heartwarming (the Pitch Perfect trilogy helped keep me sane during the first Covid lockdown, for example). But as impressive as all this sounds and is, I have to say that after chatting with Kay for my latest artist-on-artist conversation, I’m most envious of her family - which sounds amazing, as you’re about to find out for yourself.
For aspiring and emerging screenwriters, pay special attention to Kay’s unique approach to the adaptation of the first Pitch Perfect (a musical comedy she wrote as a sports film) and her pursuit of the personal even in the most fantastical of stories like Cinderella. For all artists, her reflections on surviving adversity and professional setbacks in the arts, an increasingly painful reality for many of us in the 2020s, might prove especially helpful to you as you face your own challenges.
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COLE HADDON: Kay, can you tell me when was the last time you, as an artist, found yourself sweating, your heart racing, and the words “Fuck me, I can’t do this” on repeat in your head?
KAY CANNON: This question is interesting because I can immediately name the three specific times that this occurred. The first was when I was working at "30 Rock" and was tasked with writing the hour-long Christmas episode while I was also re-writing Pitch Perfect days before it went into production while my fiancé – now husband, who is also a writer – was living in L.A. and I was flying out to see him. I was living in New York City. The only reason I could go see him was because I was out on script for “30 Rock”.
CH: How did you handle that?
KC: I basically broke up my days of that week into eight-hour segments. I would write the episode for the first eight hours and re-write Pitch for the second eight hours and then eat, sleep and try to be a person for the remaining eight hours. On the second to last day before Pitch production began, I got a migraine. I would write a line or two, throw up, and then try to write another line or two. I was stressed.
CH: [Laughter] The things we do for our art. You said there were three times you had this “I can’t do this” feeling?
KC: The second time was while I was shooting Cinderella. Everything about that production was hard. But that's the deal when you are making a studio movie – making anything – it's going to be hard. Not enough time, you're stretched to the limit. It was the first thing I had both written and directed in a genre I had never done before - directing-wise, that is. We started shooting the third week of February in the U.K. in…2020.
CH: Oh hell.
KC: We didn't have cell phones on set, so, as we headed into the first week of March, at the end of every day, I would ask my husband – who was my writer on set – "The thing happening in China, that's getting better, right?"
Obviously, it didn't get better. The week of March 9 to 13 was the hardest professional week of my life. I had already lost a considerable amount of weight - I often lose weight when I'm directing because I am so busy that I forget to eat. But that particular week, I wasn't eating because I was so afraid. I had to be the leader – the captain of the cast and crew – hundreds of people who were also afraid, concerned for their well-being, their health, their livelihoods. That last week of shooting - as soon as I got home, I would shower immediately and just...cry. It was all too much. I'd get out, dry off, and just unleash every fear I had to my husband...actually saying the words, "This is too much, I can't do it."
“It was the first thing I had both written and directed in a genre I had never done before - directing-wise, that is. We started shooting the third week of February in the U.K. in…2020.”
CH: I’m sorry. It was horrifically stressful for all of us, but what you’re describing - for an artist? Yeah, just sorry.
KC: When all is said and done, I could do it. I did do it. Almost five months to the day of shut down, we returned to finish the last eight weeks of filming. Cinderella was the only production to never get shut down again because of Covid. We tested more than 14,000 times and not one positive test.
CH: Amazing. Okay, the other time you panicked?
KC: The third time was recently. I was on the Negotiating Committee for the Writers Guild of America. I was also about to begin prep for a movie I had rewritten and was directing called My Ex-Friend's Wedding. The week leading up to the May 1st deadline was rough. It was my first official week of prep for the film. Knowing a strike was eminent, I had to get the script in as best shape as I could - with the understanding that I wouldn't be able to change a word while us writers were on strike. As a member of the Negotiating Com, it was incredibly difficult, the negotiations were stressful. But the "heart racing" part of it was that I was pulled aside and warned, "If you shoot your movie during the strike, even if you follow all the strike rules as a director, members are going to eat you alive. They will go after you on social. We are telling you this to protect you."
CH: That’s not where I expected this to go, but it does make sense in hindsight. What did you do?
KC: Ultimately, we pushed the movie. We pushed it again when the actors went on strike. And then, we lost our financing. But at the time, in that moment, I felt like every side was coming at me. After shooting Cinderella during the pandemic and now trying to do Ex-Friends, I was like, "Can't I just have a regular hard time at this? Can't I just focus on the art of this? The ‘what am I trying to say’ with this movie?" Instead, the focus had been centered on these outside forces that felt so extreme, so out of my control.
Of course, now, after being through all of this, I do feel like I can do anything. Go ahead and try, world - come at me!
CH: [Laughter] I think I’d feel that way, too.
CH (cont’d): Let’s talk about your childhood. You come from an unusually large family, don’t you? I’m curious if any of your instincts as a performer, as a storyteller, developed in response to where you showed up in the line-up and having so many other kids around to collaborate with or maybe even distinguish yourself from.
KC: I am the fifth of seven kids: Stacie, Paul, Vince, Matt, Me, Mary, and Luke. My parents wanted twelve – which I think is insane Catholic nonsense! – but my mom could physically only have seven.
CH: I mean, how did she handle that many?
KC: The woman is a saint! In the child-rearing department, it was all my mom. Once in a while, my dad cooked meat for dinner but I don’t know [laughter] if he ever changed a diaper in his life. There are twelve years between the oldest and the youngest. But it's very interesting – well, I think it's interesting – on where I fall in my family. I'm in the middle of the pack, but the oldest of "the babies." Me, Mary, and Luke. The pack is Vince and Matt – kind of Irish twins who were in the same class – and me and Mary – kind of Irish twins where I was a year ahead in school.
KC (cont’d): The four of us were in high school at the same time and college at the same time. This dynamic of being in the middle of the pack while also being treated as the oldest of the babies impacted my world view in big ways.
CH: How so?
KC: I learned how to get along with vastly different personalities – real middle child stuff – while also learning how to be a leader. Oh, and I was also the runt of the family. So, I had to find ways to be seen and heard. As a performer, I found being physical or extremely silly was a solid means to be seen. Doing something funny was easier than saying something funny. All of my siblings are funny in their own way. Stacie is bitingly sarcastic, Paul tells jokes, Vince does impressions, Matt tells a great story, I like to do bits, Mary thinks funny, and Lukeeee is more observational. I mined a lot from them.
My big ole family had dinner together every night. All of us were athletes – three of the seven went on to be college athletes. Often, our dinners were late at night, after a game or a track meet what have you. At our dinner table, you had to ask to be excused. You could only be excused if you did two things. One, eat enough of your dinner. And two, contribute to the conversation. If you were pissed off and quietly stewing with a bad attitude, you didn't get excused. My family became very good with the latter. We would sit at that dinner table for hours – even if it were late at night – and talk, gossip, laugh, sometimes argue, tell stories about our day. It was at that dinner table where I learned how to tell a story, learn to converse with anyone, rid any fears of speaking publicly. If you could kill at the table, you could kill anywhere. The Cannons are a tough crowd and they will take the piss out of you if you let them. They don't find me funny at all. I think they're still shocked I get paid to do what I do.
“[My family] are a tough crowd and they will take the piss out of you if you let them. They don't find me funny at all. I think they're still shocked I get paid to do what I do.”
CH: Amazing. I’m also just incredibly jealous of this family of yours that actually liked spending time together at the dinner table and actually talked. Nobody in my family liked talking to each other, I think, even my parents. I’m curious, you mentioned that your husband is a screenwriter and, thus, storyteller. How does he do at that dinner table? Was surviving it a price of admission to the family?
KC: The first time Eben experienced a Cannon dinner was Thanksgiving 2010, I think? That year, the poor guy wasn’t just having dinner with my siblings - he was also sitting down with spouses and many, many, many grandkids. My nieces and nephews that were mostly under the age of seven. There were, like, three to five babies crawling around. It. Was. Chaos. And what you need to know about Eben is that he is from the quiet state of Maine. He has a smart, sweet, soft-spoken older sister and wonderful parents who I would also describe as “not loud.” So, you know how when somebody borrows your car and they leave the radio on crazy loud and then you get in your car a day or so later, turn the engine on, and the blaring music startles you like nothing else? That’s what that Thanksgiving dinner was like for Eben. But he prevailed. And now I think he kind of likes it.
CH: He certainly sounds like a keeper then. Did these intense, full-contact family dinners help you later in life - especially as a writer?
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