A perfectly Midwestern Conversation with Last Week Tonight writer Taylor Kay Phillips

Taylor Kay Phillips

Taylor Kay Phillips sports her “Ope” shirt. // Photo by Mindy Tucker

Taylor Kay Phillips was born and raised in Kansas City, MO, but she now lives in New York City where she works as a writer and comedienne. Her comedy ranges from stand-up, improvisation, and musical comedy to writing for the page and the screen, among other creative ventures. In addition to writing for Last Week Tonight with John Oliver, Phillips has her debut full-length book forthcoming from Penguin Random House on April 11, titled A Guide to Midwestern Conversation. You betcha, this book is a riotous yet affectionate examination of Midwestern language and culture, and Phillips was generous enough to sit down and discuss it with us. Ope!

The Pitch: Where in KC are you from originally? How does NYC life compare?

Taylor Kay Phillips: I am from South Kansas City originally. So the suburbs, but like very close, like a block away from State Line Road. But I am from technically Kansas City, Missouri proper, which I was very cocky about when I was growing up. Because I had a lot of friends who’d say they’re from Kansas City, but when you write them a letter, it’s Overland Park, Kansas, or it’s Leawood, Kansas, or it’s, you know, whatever. But I am from Kansas City, MO. And I now live in Harlem. And they are totally different places that I both love very much. Whenever I go home, because my parents still live in the same house that I grew up in, I never moved while I was in Kansas City. And just the pace of life is a little bit different. And like, you get a little bit more time to spend with yourself in the Midwest and in Kansas City. Because like, distance is so different. I remember I have a friend who lives now in the River Market. And from South Kansas City to the River Market is like 25 minutes in a car, smooth ride, there’s never any traffic. To get anywhere in New York to visit any of my friends is 30 minutes at least. And then it’s just like, kind of all the classic things, you know, like, I walk into my coffee shop in New York, and I say, like, “Hi, how are you?” And everyone at first is like, “Who is this? What is she doing?” So, those are the big differences, distance in between stuff and like just sort of general pace of life. I don’t think that New Yorkers are rude. I just think New Yorkers are busy.book cover

The Pitch: I admire how you use humor to broach heavy topics such as bodily autonomy, or lack thereof, and gender roles. (Not necessarily in A Guide to Midwestern Conversation, but in some of your other writing, such as some of your pieces published in The New Yorker.) Where do you get your sense of humor?

TKP: Oh, that’s so interesting. Um, I think my particular sense of humor, and what I find really funny is, I think, rooted more in the absurdity of reality, than maybe like goofiness. I think that kind of stuff is really funny. It’s just not where my brain goes. There’s a quote by Kurt Vonnegut, I’m gonna mess it up. But it’s basically like, comedy is telling people the truth faster than they’re used to hearing it. And to me, that is what I find both the funniest and the most effective type of humor, is just laying out reality as I see it in a way that isn’t gilded by these kinds of proper presentation filters that I think kind of quote-unquote polite society uses. I think that’s particularly interesting being from the Midwest, because I think that people misinterpret what Midwestern nice is. I think a lot of times people think it’s a fake thing. And I don’t think that’s true. I think it’s a language. I think it’s a way of speaking. I don’t think it’s inherently dishonest. But that, to me, I think being in the Midwest and then going to New York and being other places, identifying the way people communicate ideas that are maybe different from their words, has always been very, very funny to me. And telling the truth and sort of, you know, being irreverent and cutting through bullshit and saying stuff quick has always been something that appeals to me and just saying, like, let’s all agree what we’re doing here.

The Pitch: You write in your book about the misconception of Midwestern politeness being fake or passive-aggressive: “deep-fried disingenuousness,” to borrow your phrasing. Where do you think this stereotype comes from?

TKP: I think it comes from people not asking more questions. Something that I think is specific about the way the rest of the world sees the Midwest, that I think is different than possibly other parts of the country or other countries in general, is there’s a certain element of disinterest. And there is, I think, a feeling of people talk like people in the Midwest are inherently unsatisfied, or like, stuck there for some reason, that people in the Midwest are in the middle, they wouldn’t choose to be there, but they’re stuck there. And I think people in the Midwest are like, that’s so untrue. If you spoke with us about what we were doing or how we were feeling or how we communicate, we would answer that question. That’s kind of what’s so fascinating to me about the misconception, is it is so easily debunked, if you know someone from there or ask someone a question. I think with the disingenuousness, I think that other people, there are other places where the attempt at being polite, even when you’re angry, is disingenuous. And I think in the Midwest, you are still supposed to be polite, even if you’re angry, you’re not hiding the fact that you’re angry necessarily. It’s just we don’t behave this way. Even if we’re mad, or we don’t behave this way. Even if we’re offended. We are direct, you know, saying, like, “I didn’t really care for it” is a direct Midwestern way of saying, “Get that shit the fuck out of my face.” It’s just not the way that you would say it other places, if that makes sense.

The Pitch: It’s apparent that a lot of research went into this book and each state’s profile. I laughed reading the book and it was a fun read, but I also learned stuff. What was your research process like?

TKP: I knew that I wanted to do state profiles for every state because there is such a specific feeling, I think, being a Midwesterner and going up to any book that is about the United States, in general, and flipping through and like, wondering if they talk about the Midwest, wondering if they talk about Missouri, wondering if they mention, you know, Kansas City, or do they? Do they just like, say Kansas and that counts, or is there like a food from each state? I’m always like, which one? Which one did they pick? And so I wanted to give every person who lives in a Midwestern state their own moment to say, “Haha, she did my state.” So I went to a lot of the Midwestern states, I didn’t get to all of them because of COVID. And I got a new job and all that stuff. But like, I went to Wisconsin, and I had cheese curds, and I drove through Iowa for the beer wars. I went to Des Moines and Cedar Rapids, and Iowa City, and all of these places to get the vibe. And like, luckily, I have a lot of friends from the Midwest. And I asked them, like, I sent out a Google doc to some of my friends from the Midwest. And I was like, what, you know, what is your interstate conflict? What is your state proudest of? And then I use that as a jumping off point. I didn’t just totally take their word for it. But, you know, I asked stuff that I didn’t know. The Missouri one, my dad’s from New Madrid, and so I wrote about the New Madrid fault line. And, you know, I know that some people call it Missour-uh. I personally don’t like that. And so some of it was personal, I will admit, at first.

The Pitch: I also love the “in-state conflict” included on some of the state profiles. What were some of your favorite in-state conflicts you discovered?

TKP: I tried all three of the ice creams in Ohio. So that was my personal favorite one to research. Because Cleveland and Cincinnati and Columbus all have, like, their Ice Cream Wars. And so, I did try one of each. And I can’t pick between them, they’re so different. That was definitely my favorite one to research, but the feud about where the Reuben sandwich was invented was also cool, because they’re like, “Yeah, we’ve got the menu,” you know, when you’re looking up all this stuff. And Juicy Lucy’s. I love the food ones. I love the Midwest wanting ownership over who invented something. Those were my favorite little conflicts.

The Pitch: Your breakdowns of the multi-step processes that are Midwestern Arrivals and Midwestern Goodbyes in the book are great. Which of these complicated processes do you personally find more difficult, and why?

TKP: Sometimes I find them both very easy, and sometimes I find them both very difficult. And it depends. The arrival because I am, unfortunately, an admitted social media stalker. So I usually like know stuff to say, like I saw that you did this, because when you’re coming from the Midwest, everybody kind of knows, or like somebody will have preempted you before. But going as a New Yorker and kind of being an expat now, sometimes it’s good, but also sometimes it backfires. One time, I saw somebody at a party and I was like, “Oh, my gosh, how are you? Congratulations,” because the last thing that I remembered was seeing on Facebook that they got engaged. But it had been like a year and a half and I hadn’t remembered that and their engagement had been broken. So obviously, I just wanted to crawl into a hole and die. But the Midwestern goodbye is its own monster because if you’re leaving a big event, you have to do it to everyone. And you have to do it multiple times. But also you can’t make anyone feel like you want to leave. It’s like, you have to leave, this is the worst thing ever. And I want everyone to feel good about the fact that I’m leaving. So, they’re both very difficult. But I do prefer arriving because if I arrive and I mess something up, I can make up for it over the course of the event. But if you leave weird, then all you’re doing is sitting in your car going, “I messed it up, should I go back?”

The Pitch: That’s why I prefer the Irish goodbye. Just simply leaving.

TKP: Yeah, you just gotta leave. But if I ever Irish goodbye, I always text like, “So sorry I missed you, it was so good to see you!” It’s like the Midwestern Irish goodbye. There’s several steps to it. The Irish Catholic goodbye. [laughs.]

The Pitch: You mention in your book that you have a distaste for the ongoing debate people seem to like to have about which states are included in the region. Why do you think people love debating which states do or do not make up the Midwest?

TKP: Well, I think people like to see themselves. And we all want to identify ourselves with cultural habits. And I know that there are places in the States, like I’m from Missouri, my dad’s from the bootheel of Missouri, the bootheel of Missouri is very much the South. But you know, the state of Missouri, like, I think that I’m definitely a Midwesterner. And I’ve heard people speak of Western Pennsylvania as the Midwest. And when I first started writing the book, I was like, “This is nonsense.” I gotta say, I go back and forth on it now. But for the purposes of the book, I needed a decision to be made. And as I traveled to those places, I was, for the most part, convinced that there were commonalities among everyone, but I think people want to be a member of a group, and I think we’re proud of it. That’s the thing is Midwesterners like being nice, and you know, and caring, and we like being tough about weather, and taking casseroles places, and within the Midwest, right, it’s like there’s all different dishes you bring, there’s different vibes and different beats and different hues of Midwestern. But I do think what binds us together also is the way that people from other places treat us or hearing about where we’re from, which is why I would say that Pennsylvania maybe doesn’t count, because if you tell someone you’re from Pennsylvania, they don’t necessarily respond to you the same way that they do if you tell them you’re from Nebraska or Missouri, or you know, Michigan.

The Pitch: What’s your favorite Midwest-ism?

TKP: I mean, it’s hard to pick favorites and I feel like I shouldn’t, but I have a special place in my heart for the sports ones. And for like, “that kid is special,” because being an athlete in the Midwest was such a big part of my upbringing. “That kid is special, we’ll get him next time.” Then calling people a “class act,” especially since Kansas City just won the Super Bowl. Those are deep in my heart, but also I love the ones that everyone knows. I love “ope,” I love “you betcha.” I love the ones that if you say them in New York, someone in the room goes, “Where are you from?” So, I know that was a non-answer, but it’s like asking you to pick a favorite child.

The Pitch: What was your greatest creative challenge writing this book?

TKP: I think the biggest creative challenge was making it feel fun and funny, and done in love, without sort of falling into the trap of thinking about what people from, like, not the Midwest would think. I’ve been living in New York, I’m a comedian in New York, which is a very specific kind of way of thinking. And so creatively, sometimes I had to sit with myself and be like, you know, funny jokes are funny jokes. And funny is funny. But there were times when I said, “Is this really how the Midwest behaves? Or are you pandering? Do you know what people expect and you’re making a joke for their benefit?” And the way that I grounded myself creatively was by saying, “Okay, well imagine that you’re just writing this for like, your friend you went to high school with, or, you know, the people at the bar that you watched March Madness at in 2012. You know, would they think this is funny, would they see themselves and would they feel seen and loved?” And I think that was the biggest creative challenge was to remind myself that, like, I would think that this is funny, and that people like to get made fun of when it’s in love. The first time I wrote this piece, I sent it to McSweeney’s, which is run by a guy who’s based in Boston. And he was like, “I have to admit, I was a little nervous publishing it, that the Midwest might think that we were taking cheap shots at them.” And I’m like, “No, we don’t think that, we’re not embarrassed of the way that we behave. And also, like, we can take a joke.” You know, I’m reminding myself that people weren’t gonna get offended, because I wasn’t trying to offend them. I was saying it in love the same way that you know, when you’re like, Mom’s forehead vein is coming out because she’s excited. You’re not making fun of Mom, you’re pointing out something. It’s like what I was saying earlier, right? You’re telling the truth.

The Pitch: What was the most rewarding part of writing this book?

TKP: Well, whenever I would get stuck, or feel like, every writer has this, I think, where it’s like, this is the worst book ever. Nobody’s gonna like it. I would give it to my friends who weren’t writers and weren’t comedians, and I would just kind of watch them read my latest part. And when they would laugh, or say, “Oh, my gosh, yes, I did that yesterday.” That is how I kept going. But the most rewarding parts for me are when I got really, really personal in a way that people found really funny. The day in the life of an athlete is very near and dear to my heart and writing an entire poem about the garage fridge. Being able to do all of these little things that were so personal in a way that hopefully everyone will feel really, really happy with or really seen by, in a fun way is, yeah, like a little chuck under the chin.

The Pitch: The importance of sports to Midwest culture is a theme in the book, and per your website’s recommendation, I would like to ask you about your high school basketball career.

TKP: Well, thank you. My high school basketball career and my youth basketball career was the entire inspiration behind the diary of a Midwestern youth athlete. I sit around and think, in just honest amazement, how much food I consumed and how much sports that I played in such rapid succession. There were so many years, and like with no discomfort whatsoever, I would just eat a whole bowl of Chipotle and then I would go play a basketball game where I was one of five people and like I would play the whole time. No, basketball was a really foundational part of my life. And growing up in sports, sports have always been even on the coasts, a way of communicating and relating with people. When I first moved to New York it was the year the Royals won the World Series. And, you know, you’re wearing a Royals hat, somebody else’s wearing a Royals hat, and you just like, you know, scream or whatever. Now that the Chiefs are good, way more people have Chiefs gear and stuff, but it’s really cool. I mean, sports are now how Kansas City is showing itself to the world. Which is, to me, so cool, like, we got the World Cup, we got, you know, two of the last four Super Bowls. It’s my way in to talk about where I’m from, and it’s very, very cool. And I think sports stories do so much for that. One of the most Midwestern things ever is piling a bunch of kids in a car and stuffing them with food and then taking them all to one place and piling them out and they all get in somebody else’s car, and they go somewhere else.

The Pitch: What has been your favorite experience writing for Last Week Tonight with John Oliver?

TKP: I started almost exactly a year ago, I started in February of 2022. And the way that people get those jobs, it’s different for everyone. You basically do the work outside of it, and one day, you’re lucky enough and you get the packet. It sounds really simplistic, but it’s a different path for everyone. I did a lot of online humor writing and some stand-up before the pandemic, and my husband writes for The Late Show with Stephen Colbert. So, through that, and through my own friends in the comedy community, I got my hands on the packet, which is basically the application process for the show. And then it sounds so simple to say I did it and I got hired. Because I did, but I had done 15 or 20 packets before that, and for different shows and had gotten rejected from all those. So it really is a numbers game. But I am very blessed to be working at the show. I love it. My favorite experience still is waking up and realizing that my job is to write jokes for TV. There are some days when I have to get up really, really early to finish to hit a deadline. And on those mornings, I always drink out of the mug, my mug that says Last Week Tonight. Because when you get up at five o’clock in the morning, sometimes you don’t want to be writing jokes for the TV. And when I have my mug that is like, I work there, it helps me to remember that, you know, me from a year ago, and tons and tons of other people in this world, would do anything to be waking up at 5:00 A.M. to write jokes for John Oliver, and I am one of the very, very lucky few that get to. So honestly my favorite experience is every day.

The Pitch: Can you tell me a bit about your musical comedy duo act, Dylan Taylor, and your debut EP The Love Songs? How did this project start, and what’s next for Dylan Taylor?

TKP: Yeah, so Dylan MarcAurele is an absolutely incredible musician and comedian, and we worked together on that EP. He runs an Instagram called Real Housewives of New York, the Musical. And his career is taking off in musical theater in other incredible ways. And we are right now chomping at the bit to work together again, but I’ve got the book, and he’s got Real Housewives of New York and a new musical about M3GAN, the movie. And so, we wrote that EP in COVID, basically remotely. We went to college together. He was the pianist for our musical improv troupe. needed a composer and he wanted someone to work on being funnier with which is silly, because he’s incredibly funny. He does not need me for anything. But I mean, it was my saving grace in COVID, working on that project, it was so, so much fun. He’s so talented, and I would sing every day for the rest of my life. So, I’m very proud of that EP, and I hope that we will do more stuff in the future. It’s just a matter of timing.

The Pitch: Can you tell me more about your writing group “A Great Week for Women”?

TKP: It was like February of 2017 or 2018. Wow, it’s so long ago now. I cold messaged a woman named Caitlin Kunkel on Twitter who I really looked up to and admired. And I said, “Hi, like, can we get coffee sometime? You tell me, you know, how to be you basically.” And she changed my life. She said, Yeah, I’m having a meeting of a bunch of women writers and comedians at a friend of mine’s apartment, her name is Casey, come through. And it was really shitty, rainy day. And I decided like, No, I’m gonna go anyway. And seven of us showed up on that terrible rainy day. And we are still incredible, incredible friends and sort of creative supporters. We’re all different. Like, you know, Caitlin is working on longer humor, novel projects. But she wrote a comedy book. Casey, like, just wrote a Super Bowl commercial, like as an advertising maven, but has also like, gotten published in the New Yorker a million times. My friend Sasha is a TV writer, my friend, Kate is now the Director of comedy at the Kennedy Center, like, you know, they’re all over and doing such amazing things. But we have our little group texts. We did live shows and readings, and first of all, COVID happened. Second of all, like, we’ve sort of dispersed. But we are always on the group text, checking with one another. Caitlin helped me so much with my book proposal. It’s my number one testament to what happens when you just show up for yourself and for other people. Because if I hadn’t braved the rain that day, I would never have met those women. And they’re all so important in my life and in every possible different way.

The Pitch: I am highly intrigued by the comedy game show “Citizenship LIVE!” you developed with your husband, which according to your website, “pits natural born US citizens against immigrants in a civics trivia competition.” Can you tell me what a typical show is like, and where this idea began?

TKP: That is still going strong in New York, we do it at a place called Caveat. We love it. It’s like, the thing that I’m most excited about, besides the book, and my job. So my husband is an immigrant. He is from Colombia, South America, from Bogota. And we were in the greenroom for a show that he was hosting, a comedy show with our mutual friend Orli Matlow. She’s a comedian from Canada. And the two of them were talking about, I believe the Secretary of Commerce, Wilbur Ross. And I had no idea who that man is. And he was at the time the Secretary of Commerce in the country that I lived in, that I was born in. And I did not know. And these two immigrants knew exactly who he was. And I was like, I couldn’t name you a single person in the cabinet of Canada, or Colombia. And then, basically, that’s where the idea for the show came from. So basically, we put people born in the States against people not born in the States, they might be citizens now, but they were not originally born here. And basically, we ask standard American trivia questions, and then quite easy trivia questions about the countries that our guests are from, but they’re equally as difficult for everyone on stage. So, you know, we would ask, “Who is the Commerce Secretary of the United States?” And everyone would try to answer and it’s a bunch of comedians. So like, they tell you how they got their answer. And they’re all very funny and wonderful. But then we might ask, Name one government official in, for instance, Bulgaria or wherever our guests are from. We have a monthly run at Caveat, and our next show is actually tomorrow. It’s just a freaking blast. I’m a big trivia nerd. I’m actually the 2010 Missouri State Champion in Knowledge Bowl. Competitive trivia in high school is very cool. The show is really wonderful. I’m so excited for our show tomorrow. Like, it’s just a trivia show. But comedians are around being goofy and writing, we write the questions. We have a producer, his name is Reid. And we get together and write the questions once a month. And then we go to the show. And it’s just the most fun. It’s like an excuse to go on stage and all that fun stuff. And everybody learns. We give the audience a little love. We give them pencils and paper, and they get to play along too. So yeah, we have so much fun.


Pre-order Taylor’s book A Guide to Midwestern Conversation from Penguin Random House, or find it in bookstores near you April 11.

Categories: Culture