This week, we’re highlighting 25 talented writers and performers for Vulture’s annual list “The Comedians You Should and Will Know.†Our goal is to introduce a wider audience to the talent that has the comedy community and industry buzzing. (You can read more about our methodology at the link above.) We asked the comedians on the list to answer a series of questions about their work, performing, goals for the future, and more. Next up is Rachel Kaly.
Tell us a story from your childhood you think explains why you ended up becoming a comedian.
A story from my childhood that I think explains why I’m a comedian is 9/11. I’m a born-and-raised New Yorker, and I saw 9/11 happen from my school, which was a little less than a mile away. I think seeing something so absurd happen immediately makes your imagination run wild: If that happened, what else can happen? I always saw people shooting movies on the street, and I’ve been told that my initial reaction to two planes flying into a building was that I thought it was a movie set, and I was so excited for the movie to come out because I saw them filming it and maybe I would be in it. I also think it forever changed my brain chemistry to basically be as mentally ill as possible, so my neuroses have inevitably led me to write jokes about my life for better or worse.
A more palatable story might be that my dad put me in front of the TV to watch Seinfeld for four hours a day, starting at age 6, instead of parenting or talking to me, so I was actually fathered by none other than Larry David. I guess I’m a nepo baby <3.
What unscripted or reality series do you think you’d excel at? What archetype do you think you’d be?
This is an amazing question because, like everyone else since the pandemic started, all I have been able to do is watch reality TV, and therefore I’ve given a lot of thought to this. First of all, I think I’d be amazing on a home-renovation show. If COVID hadn’t happened — because right before COVID, I feel like I was starting to go out, like, dancing, and I accepted that I was gay — I might have been more of a Real Housewife or even perhaps a cast member of a show where people have sex, but unfortunately I became a woodworking lesbian who was on Facebook Marketplace until 4 a.m. every night instead.
My dream is to build a tiny home by myself, and I’d love to do that for people for whom homeownership would change their life. I think in that sense, I’d be the personality-less giver who is typically a six-foot male on HGTV shows. But I also know after watching queer Ultimatum and Love Island that if I basically completely dissociated and embraced immense gender dysphoria, I could be an incredible femme, borderline–emotionally abusive love interest. I would, of course, need to get surgery to do this (bigger tits, longer legs, entirely new skin organ), but if the production paid for that, I would do it.
What’s your proudest achievement of your comedy career so far?
My proudest comedy achievement is unfortunately staying true to myself, and I am sorry that that is my answer. I think I have been consistent and honest in my work, even when it is not “on trend.†For example, I cannot do TikTok that well, at least yet, I think in part because my comedy is longform. Making a video under two minutes often compromises what I think is funny. Making a stand-up joke short and pithy is not necessarily where I always have fun … but alas, that is not what is beloved by the algorithm.
There have been times where I’m like, Well, I suppose I need to change the type of material I do so that I can be successful more quickly, but I think that that’s a mistake because then you just start making stuff that you think other people will like rather than what you think is funny or good or interesting. And to be clear, I think the democratization of people getting to have careers who didn’t just go to X school or know Y person but blew up on social media is seriously good. I just hope that that doesn’t become the prevailing metric by which the industry deems you worthy to invest in, because even virality is plagued by the same hierarchies that have always been annoying and bad. But honestly, probably the issue is just that capitalism is quite evil … A rather interesting observation on my part, if you think about it …
What have you learned about your own joke-writing process that you didn’t know when you started?
A couple of years ago, ideas would just come to me and I would run with them. I think I was more manic a couple of years ago and also doing improv many nights a week, so joke-writing came to me more easily when I had alt-comedy and unmanaged-panic-disorder adrenaline coursing through my body. I’ve found recently it’s harder for me to surprise myself and I have to force myself to sit down to write.
When I’m in New York, I do a monthly show at Union Hall where I write a new half-hour. If I’m remembering correctly, Carmen Christopher used to do shows where he did basically all new material, and I was like, That is very smart and good. I’ve been doing that show for about two years, and I’ll force myself to write a new 30 minutes every time but only end up keeping around two or three minutes from each show that I think is good.
I also think I’ve learned that my style changes and my voice constantly needs honing. There were two years where I got really into writing absurd and long stories that went off the rails and always ended with me basically getting killed or fucked, and it really worked for me and I think was unique. But more recently — especially since working on my new hour, which is pretty autobiographical and the absurdity comes more from how insane my life has been — I’ve been veering away from that. I was fighting against that instinct to try to do new stuff and maybe do more formally “normal†stand-up, but I think I have to accept that that’s where I’m at right now and that I can still be funny and surprising in that space.
So, I guess, in short, for me to write jokes, I need a deadline in front of a crowd so that I will be humiliated if I fail, and also everything is always changing and there is no one formula that works for me, and that is a blessing (growth) and a curse (annoying).
Tell us everything about your worst show ever. (This can involve venue, audience, other comedians on the lineup — anything!)
The worst show I ever did was when I was 10 years old. I started doing stand-up when I was 8 or 9 at the Gotham Comedy Club — they had a program called Kids ’N Comedy, which is both the worst and best thing to ever happen to me. I was the only girl in the troupe for years, and we did a Sunday-brunch show every month to an audience of 150 people (mostly parents from Westchester or Jersey who I think wanted their prepubescent sons to talk about their marriages onstage).
But at this one particular show, which was in the basement and every wall was a mirror, I did a set and it was a boy’s 12th birthday, and he and his friends were all sitting in the front row. They absolutely hated me and heckled me the whole time, saying I wasn’t funny and I was ugly and other amazing things, and I obviously had no idea what to do. So I told them to “please stop†after every punch line, and I cried after and honestly may have even cried onstage. For whatever reason, I didn’t stop doing stand-up after that, and now I beg people to heckle me because it is the most fun thing that could possibly happen to me. I challenge every man over 45 to come for me. I will destroy you, and I will buy you and your girlfriend a drink after and then we will go to a WNBA game together even if you hate women.
Let’s say we live in a “Kings of Catchphrase Comedy†alternate dimension where every single comedian is required to have a hit catchphrase. What’s yours and why?
It is impossible for me to choose a catchphrase because I think I am someone who has a new one every six months. For a long time, my catchphrase was “No problem.†That was the perfect catchphrase for me, because everything is obviously a problem, but if you say it’s “no problem,†then that’s funny. You bomb a set? No problem. You look like shit? No problem. Your family member gets hit by an 18-wheeler truck and dies suddenly? No problem. But I need a new one, so I will take suggestions.
Nominate one comedian you don’t know personally you think is overdue for wider recognition and why you’re a fan of their work.
I actually don’t know if I can follow this brief because I feel like every comedian knows each other? Especially because of social media? Am I going to get in trouble for talking about someone I know personally?
I think I’m going to get in trouble for doing this, but I don’t really care. One comedian I think is overdue for wider recognition is Conner O’Malley. And obviously everyone is obsessed with him, but I am upset that he doesn’t have his own TV channel at this point that is a 24-hour feed of him screaming with blood dripping down his face in a lake at a porn convention with Rudy Giuliani, etc. I have been a fan of his work since I went to my first show at the Annoyance Theatre in New York in 2015, and I had never seen anything like what he was doing (yelling funny). At first, I was upset because I didn’t get it and then it hit me and I was like, Oh, this is the funniest person I’ve ever seen in my life.Â
He is three steps ahead of us all in every sense, and he is on the pulse of white-male culture in a way that is actually interesting and thoughtful and extremely funny. I must give credit where credit is due: He has been squad goals for me comedically and as a friend, and therefore I want to take this section to praise him even though you said I should be talking about someone I don’t know. If I have to say someone I don’t know, I guess I will say David Schwimmer.
When it comes to your comedy opinions — about material, performing, audience, trends you want to kill/revive, the industry, etc. — what hill will you die on?
I have about 1,000 of these and have had to unlearn most of them because otherwise I will walk around pissed off all the time. But I will talk about how I think good comedy needs to be surprising.
I think sometimes people go onstage or on a TV show or whatever and just say the most relatable thing possible. And I guess that can work because people might laugh and be like, Yes, that happened to me — that is so true, and that has value in itself, but I don’t necessarily see the craft in it? If you’re just saying something true without interrogating it or making fun of it or whatever … maybe it’s a taste thing, but I think good art leaves you shocked and awed (though, of course, not just for the sake of shocking and awing). Sometimes I think it’s better to have your jaw drop than to let out a giggle. I’d prefer my audience to be silent but feel like they were struck by lightning than to get an okay-size laugh because I was like, “Yep, I’m quite gay,†and some people in the audience were like, Wait … same, and that’s kind of all that’s being said.
I think people who do what I’m talking about amazingly are Conner O’Malley, Tim Robinson, Patti Harrison, Ana Fabrega, Camirin Farmer, Ikechukwu Ufomadu, Nate Varrone, Jack Bensinger, Eric Rahill, Cole Escola, and Edy Modica, to name a few — people who are really thoughtful about the work they make, are artful about it, who surprise their audiences and I think sometimes themselves. I don’t want to be able to predict anything about what I’m seeing or watching.
If you had to come onstage to just one song for the rest of your life, what song would it be and why?
If I had to come onstage to one song for the rest of my life, it would be the opening number from Lin-Manuel Miranda’s Hamilton. Every single person in the world knows those first few seconds, and it is perhaps the best song in the world to make up lyrics to. Lin went to the same high school and college as me, and I love to give this fact, so I think it would be an amazing segue as well. In fact, full disclosure: I have a version of this song in which I compare my life to his and how his is better and he is ruining my life due to his success. Lin, if you are reading this, I would love to have you open for me.
What is the best comedy advice, and then the worst comedy advice, you’ve ever received, either when you were starting out or more recently?
The best comedy advice I received was a couple of years ago, and it was that I should only do comedy that makes me laugh. Sometimes when I have video ideas or write jokes, I’m like, I guess this is funny and I could see people laughing at it, but I felt dead while writing it and I personally don’t think it’s funny, so it is useless.
Considering myself as part of my audience has been really helpful (and incredibly painful and tedious) when I’m making or developing something. I’ve seen this especially with my show Hospital Hour, which I’ve been doing since January 2023 pretty much every month. The first two shows, I improvised completely because it was one of those times where I just booked Union Hall without having anything ready but needed to have a deadline and then I watched back those tapes and started writing it. Since then, I’ve taped the show every single time I do it, I watch it three times to see what works and doesn’t, and I rewrite at least a quarter of it for the next month. If a joke works with the audience but not me, I scrap it and start over. I think sometimes this can be to my detriment because of overworking material, but I’ve also had the help of Jack Bensinger and Eytan Boclin, who will reel me in when I go overboard on rewriting.
The worst comedy advice I’ve received was to try to play high-status characters. I cannot and will not. I am low status till the day I die. I will only punch up because punching down is, in fact, cringe and, dare I say, incredibly boring. I am weird and pissed. I am not sex positive or comfortable in my body. I am pretty much always on the verge of a panic attack or considering killing myself (no problem). It would be dishonest to be high status, and it is not funny or interesting or, in my opinion, knowable to me.
More From This Series
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- Zach Zucker Dares to Say Comedy Is About Being Funny
- Sophie Zucker Is Sick of the Irony
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