In Conversation: Esther Povitsky & Kay Cannon

Writer/director Kay Cannon and comedian Esther Povitsky at Cannon's Los Angeles home.

Kay Cannon and Esther Povitsky are proof you should always meet your sheros. The comedians and fellow girl moms are as hilarious as they are earnest.

“It’s fun that I have a 10-year-old and you have a newborn,” Cannon tells Povitsky, seated on a couch in the backyard of her Los Angeles home. “That decade difference is a nice time stop. I can look back at the time for you and I’m so excited for you.”

At the time of their conversation, Povitsky is just seven weeks postpartum after giving birth to a beautiful baby girl, Ace King, on 3/30/24.

As any new parent can attest, postpartum is a uniquely tender time when one’s world has been turned upside down by a tiny terrorist. You’re a fish out of water in your own home and life feels unrecognizable as you adjust to living as selflessly as you once did selfishly.

And yet, here Povitsky is — gamely discussing the past, present, and future — as uncertain as it all may feel for her at this moment.

“I don’t know what's next,” says Povitsky, known for her stand-up sets, indie film “Drugstore June,” Freeform series “Alone Together,” and Trash Tuesday Podcast, “because [the] baby is taking over.” For now.

Cannon, a decade ahead, has had the benefit of time and distance as she reflects on her journey from a staff writer and protege of Tina Fey at “30 Rock” in New York to becoming a successful filmmaker in Los Angeles. While perhaps best known for writing the “Pitch Perfect” franchise, she has since transitioned to directing films including 2021’s “Cinderella” with Camila Cabello and 2018’s “Blockers” with Leslie Mann.

Cannon’s biggest career moments materialized while raising her daughter Evelyn “Leni” Russell. (While it’s safe to say this would be a footnote for any male writer/director, it currently remains worth noting as we raise the next generation of future feminists.)

For her part, Povitsky — while eight months pregnant — flew to New York to perform stand-up on “The Tonight Show.”

“My doctor did tell me not to get on a plane and go do ‘The Tonight Show,’” she reflects. “I did not listen to her.”

Arguably, comedy and motherhood haven’t always gone hand in hand. But Cannon and Povitsky join fellow comedians Ali Wong, Amy Schumer, Ilana Glazer, Michelle Buteau, Tig Notaro, and Wanda Sykes in proving that’s a trope as tired as any new mom.

“The days of ‘oh, she had a baby, she’s out’ are not a thing,” Cannon tells Povitsky during their chat.

“I'm glad you said that,” Povitsky says. “Because that’s [a] thing that comes up. I hear certain actresses are not sharing publicly [that they had a baby]. They're hiding their pregnancy and baby for that reason. I’m like, ‘Oh, was I supposed to do that? Oops. I’m sorry I was so excited. I let the cat out of the bag.’”

“How sad.”

“I know. I didn't love hearing that.”

“You’ve just got to ignore that completely. I don’t care if people were uncomfortable that I was pitching shows at eight months pregnant, sweating through. It’s like, ‘Whatever, I don't care.’ You just can't care.”

“I love that. You can't care.”

“Because it’s only going to put doubt in your mind. It’s unnecessary doubt.”

Read on for Cannon and Povitsky’s honest, raw, and inspiring conversation about their respective journeys from comedy classes in Chicago to finding personal and professional success in Los Angeles…

Writer/director Kay Cannon and comedian Esther Povitsky at Cannon's Los Angeles home.

KAY CANNON: I was trying to [remember how we met]. Last night, I asked [my husband] Eben [Russell], 'Where did we meet?' I couldn't remember the first time.

ESTHER POVITSKY: You and Eben? Or me and you?

KC: Me and you. Eben, I clearly remember. I think. So, where did we meet?

EP: Okay, so I know everything about this. We followed each other on Twitter, and I don't remember [specifics, but] that was when Twitter was Twittering and everyone cool was finding each other [on there].

KC: Rob Mulaney was—

EP: Rob Delaney.

KC: Rob Delaney. Not John Mulaney. Rob Delaney was the connector for all things. That's when 'follow Friday' was a thing.

EP: Exactly. Yes, okay. So, we followed each other on Twitter, and then you DM'd me and invited me to your birthday party that you were throwing. It was you, [Alan] Yang—

KC: And Steve Hely.

EP: And Hely. It just so happened that when you had sent me that message, I was two weeks into dating [my now longtime love] Dave [King], and he was also invited to the party. Then, I got to be so cool [because I could say], 'I was invited to that party.' Because the two people you were throwing it with were his best friends, right? So, I think we met in person that night. So, it makes sense you wouldn't [remember] because it was your party, and there was a lot going on.

KC: Oh my gosh. Those parties were so stupid but fun. It was me, Alan, and Steve. My birthday is on the 21st of August; Alan's is on the 22nd; and Steve's is on the 23rd. So, we would have this 21, 22, 23 birthday [party] that we had for years. It was always at Steve's house. It was like a college party. Everybody [would] go. One year, John Mayer came. Daft Punk came. Or at least we think they did. Marisa Tomei came one year. We were all a bunch of comedy writers; so, managers and [industry insiders] would tell their talent to go to our party because it was a bunch of writers.

EP: Whoa, I feel like that's not a thing that happens anymore.

KC: No.

EP: That sounds like a golden-era situation.

KC: But that's so funny. It's all coming back to me now about how we connected on Twitter first.

EP: You and Eben were already married. Your husband and my boyfriend were [part of a] college best friend group. Then, we started hanging out more regularly. And it was so cool because I already knew who you were.

KC: And I was a fan of yours.

EP: So, it was sort of a strange [connection]. I felt like I got so lucky. Because just following you on Twitter – that's no guaranteed friendship, you know? I had to be dating the right guy.

KC: It's a baby step.

EP: It all worked out.

Writer/director Kay Cannon and comedian Esther Povitsky at Cannon's Los Angeles home.

GROWING UP

KC: We're both from Illinois. Yes, so that was the thing that we were able to connect with.

EP: Yeah, you're from really southern [Illinois], right?

KC: Not super southern, but I'm in between Joliet and Kankakee. You know the movie 'Planes, Trains, and Automobiles?' You know when they're sitting outside of a motel on their luggage literally in the middle of nowhere?

EP: Yeah.

KC: That was filmed in the bigger town [close to] where I'm from.

EP: That is crazy.

KC: I'm from a town of less than a thousand people. I think there's a thousand people now, but at the time [there wasn't]. I have six siblings. So, me and my six siblings, mom, dad, and my grandfather [who] lived with us for three years, we made up one percent of the town.

EP: No!

KC: And we weren't even the biggest family. The [family] down the street had 11 kids. They made up 1.5 percent of the town.

EP: This is what blows my mind about you because you're this successful [filmmaker]. When I met you, [you were a] successful writer/producer. Now, you're this huge studio film director, but to know that that's where you came from in a world where now – if you're not a nepo baby – you might as well pack your bags. That blows my mind about you.

KC: It's thanks to Tina Fey – and Lorne Michaels, by extension. When I was directing 'Blockers,' a producer on 'Blockers,' his wife was from around where we're from. She asked me, 'How did this happen? How did you get here?' And I [said], 'I think if I stopped to think about it, [I wouldn't believe it]. I would stop, crash, and burn.'

EP: You would freak out.

KC: Yeah. I don't know. I just was always looking forward. I was excited to ride the horse in the direction I was going, you know what I mean? I'm an anxious person but I think I had confidence, maybe, because I was from a small town, and I was a good athlete but in a small town, [so] I had this confidence that I could walk into a room and be able to talk to anybody.

EP: That's interesting. I feel like I have that feeling too. I was not a good athlete; so, I don't know why I have that. But what was your sport?

KC: I did track and volleyball in college, but then in high school, it was basketball, track, volleyball, and stuff like that.

EP: Wait, where did you go to college?

KC: Lewis University, like a D2 school.

EP: Oh wow, were you ever going to pursue sports?

KC: No, because I wasn't good enough, but I loved [it]. I always say that 'Pitch Perfect' – which was my first screenplay – is a sports movie.

EP: It is. When I think about it, [I realize], 'That is one of the well-observed things about that movie—how it nails competition.' Usually, things aren't represented the right way and in that movie they are. Because I did poms [dance] competitions and that came up for me when I watched the movie. Also, I remember the night it came out, we all went out for pizza in your neighborhood. [I'm] just flexing that I was there from the beginning. You and Eben took everyone out for pizza. It was really fun.

KC: I remember, after the first weekend, I was working at 'New Girl.' I was in my office, and I was having a bagel and a juice, and I had a weekend of partying and having fun and J.J. Philbin walks by and she's like, 'There she is!' I looked like crap and was eating a bagel, like, 'We're going to go over episode 205.' … I want to go back to your growing up. Talk to me about your confidence and how did that manifest? Because you have a sister, right?

EP: Yeah, I have an older half-sister. She's seven years older.

KC: So, did you feel a little bit like you were raised [as] an only child?

EP: Yes, and I just recently read that if there's a six-year age gap or [more] you [are essentially an only child]. Some professor somewhere says that you're an only child. It starts over.

KC: That makes sense.

EP: I've always said that I have all the negative qualities of both a younger sibling and an only child. Which I think my family would confirm. I grew up dancing and probably similar to your sports, [I took it] very seriously and thought maybe I was going to pursue that until I realized I was five feet tall and was maybe not fit for it.

KC: Were you five feet in kindergarten and you just never grew?

EP: Yeah, I started out really strong.

{They laugh.}

Writer/director Kay Cannon and comedian Esther Povitsky at Cannon's Los Angeles home.

A CAREER IN COMEDY

EP: I was a dance major at [University of Illinois] in Champaign. I remember being at the ballet bar and was like, 'Wait, that's so weird that I've chosen a career where I don't talk.'

KC: Interesting.

EP: It just hit me [one day]. I was like, 'That's really weird,' and then I started putting pieces together, and I [realized], one of the things I loved so much about dance class was being the class clown there and making all the girls laugh. I love dance, too, but those were two little thoughts that caused me to drop out of school and move to L.A. I knew that I wanted to be in comedy; I didn't know to what degree. I knew I couldn't stay in Chicago because I knew if I stayed at my parents' house [I'd get too comfortable]. I grew up in Skokie, like 40 minutes away [from the city, so], I knew that I would never get off the couch. I needed to be a little scared, and so that's why I moved to L.A.

KC: By yourself?

EP: I was like, 'I don't know anyone.' I needed to feel like there was no plan B. I'm curious. When and why did you decide [to do] comedy? What did you want?

KC: I'm the same [as] you. I always knew I'd be in the comedy world because when I was in school, I got a laugh at something and then I pushed it a little bit harder and got a bigger laugh. I was like, 'Oh,' [and realized I liked the reaction I got from people]. But, again, I'm one of seven [kids in my family]. There were rules at our dinner table. The only way to be excused [from the table was] if you ate enough or if you contributed enough to the conversation. If you had a bad attitude and just sat there like a bump in a log you were not allowed to leave the table. We all got really great at having these long dinners [with] a lot of laughing. I'm in the middle of the pack but I'm the oldest of the babies, and I was kind of the runt, too. So, I had to have a 'look at me' kind of thing contributing to the conversation. All my siblings are funny in different ways. So, I feel like that dinner table prepared me for the world of comedy. I learned how to tell a story at that dinner table. They were a tough crowd; so, I would try out different things and if they didn't laugh, they would make fun of you endlessly. So that's how I knew [comedy was of interest]. But I also loved school; so, I have a master's in education that I have never used. Except in the school of life, the learning that exists outside the classroom.

{They laugh.}

KC: So, I loved being in school and loved education and that whole world. I thought I would perform in front of a classroom [as a teacher]. But I went and saw a Second City [comedy] show when I was in college and I [realized], 'That's what I want to be doing.' I just loved it so much. Rachel Dratch, Kevin Dorff, and Stephnie Weir [were] in that particular show. I was like, 'That looks like they're having the time of their lives.' I also felt like I had a face for comedy, too. And theatre as well. I have a theatre degree, [but] I would never be able to do something dramatic. It doesn't read well on me. I have a theater face. It's all good. There was a Second City Conservatory and there are classes you could take. I was like, 'Oh, that's a path.'

EP: You're reminding me. I remember now. For my 13th birthday, my parents took me to Second City for a show. I had the same thing where I was like, 'This is the best thing that I could have ever seen. They are having the most fun. We are having the most fun watching them.' It really did leave [an impression]. That probably was an early [memory of], 'Oh, that is the goal.'

KC: And that you could do that for a living.

EP: Although, can you? Because I also remember when I was college age, and I was going to iO [Theater for improv], doing classes, I would go every night over the summers and would watch all the shows. Then, once I saw one of the performers coming from their waitressing job, and I was like, 'Oh no. You can't make a living doing this thing.'

KC: Well, a very small percentage can. Because that was the goal – to get on the main stage, right? If you were on the main stage, you were equity. It was an equity show at Second City. At the time when I first started, I was temping [by day] and every night, I had something. I was interning at iO. I was doing comedy sports. I was taking classes at the Annoyance [Theatre & Bar]. I was taking classes at Second City. I was on a team at iO, so I was doing the Harold rehearsals and then Harold shows on the weekends. It was non–stop for almost a year. Then, I got hired by Boom Chicago. Boom Chicago was a way that you could make a living. [It's based] in Amsterdam, [Netherlands]. Seth Meyers, Ike Barinholtz, and Jordan Peele all [came out of] Boom Chicago. A bunch of people did Boom. … They would hire Chicago improvisers for at least a year to come out and perform sketch and improv shows in Amsterdam and all over.

EP: Was it fun?

KC: It was amazing. It was incredible. Then, you'd come back to Chicago after having this amazing experience, and [you'd have] all this confidence, and then such a small percentage of [those] people would ever make the main stage [in Chicago]. That was probably the hardest job. I remember crying after an audition that didn't go well to get on the shortlist to be an understudy to the touring company of Second City. That seemed to be the hardest job to get. Even more than a job here [in Los Angeles].

EP: Yeah, no, I feel the same way. I still feel that way about a UCB team in L.A.—even though that's not what Second City was [like]. I do feel like making it on those stages is harder than booking a commercial or something.

KC: I think so, right? [There's just] so much competition.

CANNON’S PATH TO DIRECTING

EP: It's crazy to me, though. You are a movie director. Was that ever a thing you thought would happen [and] that you [knew you] wanted? At what point did you [realize you wanted to direct]? Was it after you wrote this huge, successful film? [Were you thinking], 'Maybe I can do this?'

KC: [I started to think about it during] maybe the fifth or sixth season of '30 Rock.' Because I had been an actor and a performer, I felt like it was something I could be good at. When I got my master's, I was a grad coach. I went back to the same place where I ran track in college. So, I knew I had the propensity to be a director who could—

EP: Be a leader.

KC: Yeah. I've been a captain on every sports team I was on. But I have such a respect for school and for people who go to film school, and I didn't go to film school. Around the fifth or sixth season of '30 Rock,' I was so often on set as a writer. I just didn't have the balls to [say], 'Hey, can I direct an episode?'

EP: It's hard.

KC: Then, [I'd] see a couple of other people [who were my] contemporaries who were getting a chance to do that. I just didn't have it in me [to ask at the time].

EP: By the way, were you with '30 Rock' the whole time?

KC: Until the very last season, which was a short season for them. Season seven had thirteen episodes. Eben and I had just gotten married. We were trying to have a baby and so that's when I moved here [from New York].

EP: But did you start at season one?

KC: Yeah.

EP: Was it your first writing job?

KC: Oh, yeah. That's why I'm thanking Tina Fey and Robert Carlock. Working at Second City was such a huge accomplishment and not getting fired from '30 Rock' was my proudest moment, you know? Because the level of [talent was incredible]. I feel like I went to grad school for comedy writing [by working on that show]. It was amazing. I learned so much while I was there. Then, when I was at 'New Girl,' [I met with] Nathan Kahane, who runs Lionsgate now, but at the time had [a film production company called] Good Universe, which is like [David Ellison's] Skydance. It [acted] as a producer and a studio. He had been wanting to work with me. He took me out to lunch, and he said, 'Aren't you tired of other people directing your material?' I hadn't had a conversation with him. He had just known my work and been a fan of my work. I was like, 'Yeah, I guess so.' Then some time went by, and 'Neighbors 2' was doing a writer's round table, and they had asked me and a bunch of other women [to consult]. Because 'Neighbors 2' is about the sororities, [they asked me] to come in to help them for this round table. I always take that kind of stuff seriously. I prepare. I think about notes and try to really help. So, I came in; it [was] Seth Rogen and Nathan Kahane, because Point Grey [Pictures] with Seth Rogen and Nathan were the producers of it. I did my thing in the room. Nick Stoller was the [film's] director, and I was giving my notes on my computer. Seth was sitting next to me. And I had no idea, but in that session, I [had] auditioned to get hired to be the director of what would end up becoming 'Blockers.'

EP: Really?

KC: At the time, it was called 'The Pact,' and when I left, they were like, 'We think she should direct The Pact.' I had earned a job there. They were hiring me based on [my] potential and what they saw in that room. I had no idea. I was just doing my thing and saying, 'Yeah, but shouldn't it go like this?' I wasn't holding back.

EP: I didn't know that. It sounds like you nailed it…

KC: Well, I had showrun, too. I'd showrun 'Girlboss,' [which] I had created. I asked Netflix if I could direct an episode of 'Girlboss' and they said, 'No.' They said, 'No first-year showrunners. We don't allow that.' But I learned so much from that [show]. I shadowed every director who worked there because it was all through me. Because I was the showrunner and the creator, so I was the final decider.

EP: This is what I always think about TV writers, especially ones who are on set all the time, whether you're a showrunner or just the on-set writer… you know how to direct. I know there are things that you don't know [or still need to learn], but to me, in comedy, in my experience, that's the person who's the most prepared to start directing because they are pitching the jokes.

KC: They produced it. They've cast it. Everything goes through the writer on a television show.

EP: If I was producing, I would [say], 'Life hack. Look at who are the best on-set TV writers, and they'll probably be great directors.'

KC: Sonny Lee, who did 'Beef,' he was on 'Girlboss' with me. [During the Emmys], he won directing. He won writing. He won Best Limited Series. That's a great example of a comedy writer who has been on sets for years [and] has his own story to tell. Then, he can direct it, and he has a vision.

POVITSKY’S PATH TO TELEVISION

EP: Wait. I have to bring it back to me for a quick second.

KC: Please!

EP: Were you [a writer] on 'New Girl' season one?

KC: No.

EP: Oh, darn. My first ever TV job was being on 'New Girl' season one for one episode.

KC: How was it?

EP: I was young and stupid, but it was fun. I loved it. Zooey [Deschanel and] everyone was nice. It was cool to watch the BTS of how things worked there and Liz [Meriwether, the show's creator,] pitching jokes. It was cool to see all that go down. I felt like I learned a lot.

KC: For you to do your own show. Which we've got to get into.

EP: But [first, I have to share], I had two terrible auditions for 'Neighbors 2' that I totally blocked out [until now]. But I'm remembering now. I had a callback for 'Neighbors 2,' and the casting director asked me, 'You're a stand–up [comedian], right? Can you do some of your stand-up [material]?' I [said], 'No.'

{They laugh.}

EP: I remember I went home, and Dave [said], 'You said no?!' You can't do stand-up in an audition room. It's just weird.

KC: Like, 'How's everybody doing in room 3E?'

EP: 'Any anniversaries tonight!'

KC: 'On Paramount Lot Stage 59?'

EP: I felt so uncomfortable with that question. I was like, 'No. I can't do it.' Anyway, that's what was happening with me during your jobs.

KC: But then [your show] 'Alone Together' happened. So, how did how did that happen?

EP: That's a good question. At that point, I had done a couple of little guest things on TV and was involved in stand-up. I was friends with another stand-up comedian, Ben Aflalo. He and I were best friends, and it was completely platonic. Every time we would go to an event, people would be like, 'What's your guys' deal? This is weird. You guys look like you're a couple,' because [why]? Oh, because we're both short, Jewish, and ugly. Like, what? Why? No.

KC: How dare you.

EP: Then, we [figured], 'Okay. Let's do something with this.' Then, we [realized], 'We need someone who's smart and not just a stand-up comic [to be involved].' Me and Dave were sitting next to you at a wedding. I was like, 'Hey, Kay, would you showrun my show?' which is very much something that would probably offend someone else. But, because you said that when you showed up [to town] you would just talk to people and ask things, you probably didn't think anything of it.

KC: Not at all. In fact, the first thing I thought was, 'Could I do it?'

EP: I love you.

KC: Because at the time, it was a lot of craziness, which is why I couldn't.

EP: You had so much going on. Dave was like, 'What are you [doing]?' Then, you go, 'Why doesn't Eben do it?' And I was like, 'Great!' Then, your husband co-created our show with me and my friend. It was amazing. He's incredible. So, thank you for suggesting him.

KC: Well, you know how those white guys need all the help in the world to get jobs.

EP: Well, it's true. He was sitting right there, and I looked right past him. So, you're not wrong.

KC: Were you sad when that ended?

EP: I was, but… I wanted it to keep going, but I was so beyond unbelievably grateful that I had a TV series for two seasons. I could not believe I got that opportunity. I don't know if you have this where… You know where you started, so any little thing is the biggest deal.

KC: I totally have that. I'll be in these budget meetings and they're like, 'The budget is only 45 million.' Having come from no money, I'm like, 'Guys, that's a lot. That's a lot of money.'

EP: We'll make do.

KC: [It's] finding creative ways to [use the budget]. I always think that you get a better idea when you don't have everything at your disposal. You have to work harder. Being scrappy and figuring it out, you get a better result.

EP: I agree. Or you cut stuff that you didn't need. I love a shorter movie personally. I did like a low-budget indie a couple of years ago and because of the budget, we had to cut scenes. I'm like, 'I think that's great. I think it's better now,' so I agree.

IMPENDING MOTHERHOOD

KC: I think I've told you this, but I wanted to say it to you again. I was so impressed and excited for you when you were eight months pregnant, and you were still doing [comedy] shows. That was incredible.

EP: Oh my gosh. Thank you for saying that. My doctor did tell me not to get on a plane and go do 'The Tonight Show.' I did not listen to her.

KC: What was that like? 'The Tonight Show?'

EP: I hated pregnancy. Wait, I forget. Did you hate pregnancy?

KC: I was so happy that I, finally, was pregnant… Did I like the physicality of it? No. It was terrible. I told you. I was over 200 pounds.

KC: I was so uncomfortable.

EP: The whole time?

KC: Yes, the whole time. I was really sick. The classic first three months where you're sick. Then, as soon as that stopped, I had this acid reflux that was 24 hours a day for some reason. I [was] like, 'Oh, something [is] going on in my body. It's not what I'm eating. Something is causing this extreme discomfort all the time.'

KC: Because there's this human being! There's something happening around here?!

EP: I don't know what it is.

{They laugh.}

EP: I think I [felt] like, 'I don't know what life is going to be like after [I have a baby],' so I wanted to add as many tour dates as I could before [I gave birth].' I had worked on all this material, and I thought I was going to shoot a special. Then, when I got so sick from being pregnant, I was like, 'That's off the table.' So, I [thought], 'I just want to get the most out of this hour of comedy.' So, I added as many cities as I could towards the end. Flying was painful.

KC: Did you wear compression socks?

EP: No, I should have. I took one of those lacrosse balls… You know like a muscle ball? And the whole flight I was rolling around on it. Literally the whole flight. Every flight.

KC: Were you in business class? First class? Or were you in coach?

EP: Sadly, I flew Southwest [Airlines] quite a bit because that was most [accessible].

KC: You've got to give yourself a perk!

EP: A couple of flight attendants would come up to me and be like, 'Are you okay?' I was like, 'No, no, no. I'm fine.' But it was fun [being able to do 'The Tonight Show']. I'm so glad that I did it. Because now that I do have the baby, I don't understand what touring would look like. I don't know. I'm glad that I got it in when I could. It was fun. I felt so proud to be so pregnant and still living life and doing things. Even though I wish that I was having that mother goddess pregnancy where I could show up and kill it in front of and for everyone. But I was miserable. But I still did it and I'm glad I did.

KC: I did a ton of prenatal yoga, and I worked out a lot when I was pregnant. I was still gaining weight. At prenatal yoga, I was maybe 15-16 weeks along, and all these women that I was with [were smaller than me]. You would say, 'Hi. My name is Kay and I'm having a girl.' And you'd say how long far along you were. There would be like these like model-y, actress types in there and they would be like, 'I'm 38 weeks,' and they were smaller than I was. So, I found myself lying.

{They laugh.}

KC: 'I am 27 weeks along…' And then they'd see me three weeks later, and they'd be like, 'What?!'

EP: Your baby's stuck in there!

KC: 'I'm finally halfway.'

EP: Oh my God, that's so funny.

KC: But I had like a similar thing where I was working up until [I gave birth]. Because I had sold a pilot to CBS. It was called 'The Runt.' It was about the runt of her family. Jason Winer was the producer with me. We sold it to CBS, and I remember emailing him [while] I was in labor and didn't realize it. I thought it was Braxton Hicks [contractions]. I was emailing him, and I was like, 'If I go into labor tomorrow – here's the latest outline. We can talk about the outline tomorrow unless I go into labor.' I was in labor, but I didn't realize it. … Then, two hours later, my water full-on broke. I just didn't realize that those were contractions.

Writer/director Kay Cannon at her Los Angeles home.

LABOR OF LOVE

EP: Was it painful? Was it not?

KC: It wasn't so bad, [but] I have a pretty high tolerance for pain. Because I was so big, the doctor [said], 'You might not [make it to your due date].' Her due date was October 9th, which is when she was born. She was born on her due date. But [I'd been told she could be born] up to October 23rd. I was like, 'No that's not happening.' So, we went to Caioti [in Studio City], which has this particular salad – the induction salad, [which reportedly helps kick-start labor]. I had that, and then we went to see 'Gravity' in the movie theatre hoping the sound [and vibration] from it [might help] and it worked.

EP: That's amazing.

KC: Then, we went to [the hospital], and I remember throwing my keys to the valet and being like, 'I'll see you guys tomorrow. I'm about to have a baby.' Then, I left a week later because I had an emergency C-section. I was in labor for 36 hours and I had two epidurals. I ended up having three epidurals, but they didn't work. They would work for 20 minutes.

EP: What do you mean? My older sister was telling me that she got the epidural, and it didn't work. I always assumed that was just a big sister lie to scare me. So that's real?

KC: I guess there's a 1% chance that it doesn't work, and I didn't pay attention in the classes leading up to that. [I didn't realize] that could be a thing. I was like, 'Oh, it really hurts.' My doctor happened to be checking on me at the time, and this [was] probably like hour 25. Lenny was four or five centimeters. I waited 22 hours before getting the epidural. I was in so much pain and he [said], 'She wouldn't be acting like that if [the epidural] was working,' because they didn't want to give me another one. That's when [I realized] they don't know where the medicine goes because I didn't feel anything in my left foot for like 20 hours. I was like, 'Oh, it just all went there. Is that normal?' At one point, at hour 30, I'm like, 'Am I going to die? Because I can feel everything.' [At that point, I'd] been up for two days because my water broke at night. So, I wasn't able to sleep. I remember calling my doctor at six in the morning because I was still only six centimeters dilated and it was [going on] 36, 37 hours. I was like, 'You need to get here. I gave it the old college try. I'm not going to be able to push even if you want me to. I'm too tired. I can't do it.' Then, she was big. And I am small. He [said], 'It's good that you did a C-section because you would have probably had to, anyway. She was trying to get out.' The blue sheet for some reason was way too close to me and then they were doing construction next door.

EP: You're like, 'You guys, be careful, please. '

KC: I was like, 'Is that you guys?' I had had so many drugs that I was shaking. They're like, 'Don't fight the shakes.' I was like, 'I'm not fighting anything. I'm just shaking.' Then, they brought in 10 doctors, because I was a geriatric pregnancy, and they wanted to show them. They were a teaching hospital.

EP: There were 30 people teaching the class.

KC: One felt bad because I was shaking so hard. Poor Eben was behind me. Then, they pull her out, and I hear, 'ah,' the cutest little [sound]. [It wasn't] even a cry. And then [there was] whispering. …. Because there was so much whispering, I was like, 'Is she okay? Is there something going on?' Because she had been trying to get out for so long, she had a massive cone head. They were whispering to Eben, 'We're going to put a hat on her. In an hour, it'll look fine.' They didn't want to scare me. How was it for you?

EP: I had been terrified of pushing and the concept of labor—all day, every day, the whole pregnancy. I was so scared. Then, I decided to get induced. So, I got induced [at] 39 and a half weeks because I [felt] like, 'Let's get the show on the road.' That was the decision I made; it was my choice. It wasn't like my doctor made me or anything. Twenty-four hours of labor, and then she came. The epidural was amazing.

KC: So, all your fears went away?

EP: Absolutely. The labor and delivery were the best part of the whole experience for me. I loved it. I was in a lot of pain, and I guess I got my epidural earlier than most, but I was like, 'That's okay.' I guess I like having my legs feel like wood and having a [urinary] catheter in. Because the whole pregnancy, especially that last month, you're getting up to pee so much that when there's a catheter in and suddenly you just lay there? I loved it.

KC: I had a constant fear of pooping on the table. I didn't do it. I don't think.

EP: I did fear that. No one told me if I did, I'm pretty sure I didn't. I feared that too, which is so lame, who cares? I almost don't want anyone to know that's a possibility, so they can just go in and party.

KC: Is there anything you wish somebody would have told you going in?

EP: That's a really good question.

KC: Or even after having Ace?

EP: People said, 'Labor is not that bad.' I just didn't believe it. People were like, 'You will know how to push.' So, that's what I would say, 'Your body knows how to push.'

KC: Your body knows how to have a baby.

EP: Yeah, and it's not just your body. Because I felt so disconnected from [my body]. I'm like, 'My body? What is my body? I don't understand what you mean.' Your brain [understands what to do]. You will know. And if you get the medicine – and it works (sorry to you and my sister) – but if it does work, it's not scary.

Writer/director Kay Cannon and comedian Esther Povitsky at Cannon's Los Angeles home.

CONNECTED SOULS

KC: I feel like you and I had an opposite experience right after having the baby, [too] because I was so tired and drugged up that when they put Lenny [on me]… I want to preface this by saying Lenny and I are connected souls. I couldn't imagine [doing life without her]. We're [closed]. But when I gave birth to her, they wrapped her up, and they put her here [on me], and I [felt disconnected]. I didn't have a 'Yeah, great, I love you so much' [immediate connection].

EP: I didn't either.

KC: You didn't?

EP: She had to go to the NICU. So, I think that caused nervousness when they brought her to me. When she was born, they took her [and] worked on her for 30 minutes, and then they [said], 'Okay, we do want to take her to the NICU.' She ended up being fine, but before they brought her [there], they were like, 'Let's put her on Mom.' I was like, 'What? No, send her to the NICU. It's fine.' So, when they did put her on me, I was very disconnected. Then, when I went to my hospital room that night without her... I look back on that and it's so crazy… 'I had a baby. She's not here,' [but] I didn't feel like, 'I need to be near her,' because I was so drugged up and sick and tired. It took a couple of days to get that strong bond.

KC: I feel the same.

EP: I don't feel that the bond is any less. In fact, I'm like, 'It's actually superficial if you just lay your eyes on them. What is it about looks? No. You've got to build it up.'

KC: 'She doesn't look like me.'

EP: 'Yeah, next.'

{They laugh.}

BALANCING KIDS AND CAREERS

EP: Okay, so you get the job to direct 'Blockers.' That's post-'Pitch Perfect,' I assume?

KC: Yeah, 'Pitch Three' and 'Girlboss' happened at the same time. Then, I got let go from 'Pitch Three' because I was doing 'Girlboss' and also [because of] creative differences. I don't know how I got credit on that movie. There were so many writers after me that I got it because I was the first writer.

EP: But I think it also adds value to a project to have your name, so that's cool.

KC: I love those Bellas so much, too. I love that cast. So that was happening. I remember 'Girlboss' came out when I was location scouting for 'Blockers.'

EP: That's rollover. That's crazy. And you had a kid. You had Lenny at that point.

KC: She was [a] baby for 'Pitch 2.' She started preschool when I did 'Girlboss.' So, she was two and a half years old.

EP: Did you have, at that point, the mom guilt? [The] mom-work struggle?

KC: I've never really had guilt because I know that I'm her best mom. You know? Because I'm her mom, I know that I'm her best mom. And I re-prioritized. I would never be on the staff of a show that wasn't my own, because you can't put all those hours into it and be away from your family unless it was [your project], in which you can dictate some stuff if you're the boss. We learned the word 'temporary' quickly. 'Just for these couple of months, it's going to be hard,' you know? Up until the pandemic, it was crazy. Then, the pandemic slowed things down, but I still had to go back at the end of 2020 without her to London to finish a movie ['Cinderella' with Camila Cabello and Nicholas Galitzine] for eight weeks. That was terrible because it was the pandemic, and we didn't have vaccines and I didn't want to be away from my family. That was crazy hard. And it was hard on her, too. I had a movie I was supposed to shoot last year, and then the strikes happened. Then, that movie fell apart. So, for the last three years, I've been at home writing. I have things on the brink, and I think those things will happen and we'll get back into this 'crazy town' time again. But, for the last three and a half years, I've been home and drop her off at school. When I thought I was doing the movie [that didn't work out], I was in Boston for a week, but it's not too bad.

EP: Yeah.

KC: The biggest thing… If I can give you unsolicited advice…

EP: No, I want it.

KC: Having a newborn… Because you talked about touring and 'what would that look like?' She will not remember anything. I mean, [Lenny] doesn't remember preschool now. I thought that she would. Especially that first year, the only one who is giving you guilt is you. They are fine. I would say do the most things in that first year.

EP: Really?

KC: Yeah. Because when they get to be two, three, four, or five, there's developmental things that you want to be there for. I wanted to be a mom; so I want to be with her, but I think [it's] healthy [for her to see] you at your best and the best version of you. You doing what you do—what fills your cup up—is so much more important than if you are missing a couple of days because you had to do a tour or a show.

EP: Well, I love what you said. 'I'm her best mom.' I want to make that a mantra because that sounds so [right]. I believe you. You're correct. You're [Lenny's] best mom. I'm [Ace's] best mom. I know that's true. I feel like I can lock into that. The other crazy thing [about] being a new mom is I feel I've become both so much more important to myself and so much less important to myself.

KC: In equal measure, you think?

EP: Kind of. On [the] one hand, I don't care about my needs. If I'm a little hungry or uncomfortable that does not matter at all. I just want to be caring for this baby and then, also, I'm more important. Because I'm her mom, I'm so important. I need to respect myself. I need to care about myself. So, it's a big shift for me in these two different directions. I'm having to adjust to it. Did you feel anything [like that]?

KC: Oh, yeah. We talked about this. I was shocked at how worried I was. I was always going to be [worried about] her and her well-being, but I was shocked at how worried I was about me dying. In a way that I hadn't ever before where I was like, 'No, no, I need to be here. I am her mother.'

EP: Suddenly, you're very important.

KC: Yeah. I agree with you. [It's] the same thing. I don't mind being hungry or if she's sick, I have to walk her around here at two in the morning because she has the sniffles. All that I love. Even if I have to go to the bathroom, it's okay. But the worry of picking a flight to go somewhere became [a] serious endeavor. Should I go on the early morning one? What if something goes wrong on the early morning one?

EP: You're checking the weather.

KC: That has gone away.

MOM GOALS

EP: It's been so fun to watch Lenny grow up. You guys as a family [are inspiring]. It's good family goals for us because you guys are so close. Also, the conversation we're having now [is so helpful]. You are such a good mom. You guys are clearly best friends, but you have your own, very full life that's yours. I'm so glad that I'm not only seeing that from afar but up close too, and we're talking about it. Because these are the things that I need to be feeding into my soul right now.

KC: There's nothing you can't get over. As long as you're having the conversation, right? Resist-persist. If you don't talk about the things [it creates a problem]. Like I was saying, the word 'temporary' with Lenny was something we learned early on. We have constant conversations about everything. I want to make it so that she [knows she can depend on us]. You want your kid to call you when they're in trouble because they need you – not because they're afraid. It's that kind of thing. That's how I feel with Lenny. Then, we also joke around a lot about how we're not best friends. It's like, 'No. I'm your mother and you're my daughter, and we are very close, but you're not my best friend and I'm not your best friend.'

EP: That's so healthy. Because to me, I look at this girl and I'm like, 'I am your only friend forever. Say it back to me.' So, I'm going to need to cool off. Back away.

WHAT’S NEXT

EP: I'm curious, though. I know you spent a long time committed to the [Writer's Guild of America] and that was a whole thing. So, now that you're back, what's going on for Kay? What is next? What do you want to do? Is it more film directing, [or] writing? What's coming up?

KC: I can't say the specifics. Or I can, and you just won't put them in there, right?

{Right. They discuss Cannon's top-secret upcoming projects.}

KC: So, what do you have going on?

EP: I just put out my indie [film, 'Drugstore June']. Then, I don't know what's next at all. Because I think [the] baby is taking over. Dave [and I] have been throwing some ideas around. Maybe trying to pitch a TV thing, but I really don't know. What's your advice?

KC: I think it's breathing through it. We're very similar. We had a bunch of stuff happening all the time and it was constantly rolling over. That's the hustle that never goes away. You have to have four or five things happening because you never know what's going to happen. Then, once in a while, nothing's happening, and you have a moment where you can sit and figure out what it is you want to do. Now that you have a baby that thinking might change slightly or at least your priorities [might]. It's like cutting scenes for a budget. What scenes do you need? It's [deciding], 'What do I want to do that is important to [and] fulfilling to me?' [while] also keeping her in mind. [It's] that balance. When I've had that experience, I've been extremely afraid and not happy to be in that moment. I guess my advice would be, 'Lean into it and know that because you are you, you're always going to work.' You're always going to get something because you're an idea person, and you're funny and very talented. The ones who don't work are the ones who stop working. And you're not going to stop working. You're always going to keep working. You've got the ideas. As long as you have an idea, you will always work.

EP: Interesting.

KC: Because you're a creator of something. You don't have to wait for somebody to give you something. So, I would embrace [that]. Lean into, 'Wow, I get a second to [ponder what I want].' It's scary. But I would remind you, also, that there are people talking about you right now, and that things are coming your way that you don't even know [about].

EP: That's nice. … Oh my god, I'm so inspired. This is so exciting.

Comedian Esther Povitsky and writer/director Kay Cannon at Cannon's Los Angeles home.
Next
Next

In Conversation: Amanda Kloots & Hilary Shor