By Jill Draper
If you’ve lived in the Midwest for any length of time, you’ll probably see yourself in the pages of Taylor Kay Phillips’ new book, A Guide to Midwestern Conversation.
From “it’s not my favorite” and “that kid is special” to “jeez Louise” and “that’s different,” Phillips deciphers the meaning behind everyday sayings in a style both affectionate and self-deprecating. And humorous.
Phillips, a former Barstow High School grad who grew up in south KC’s Verona Hills neighborhood, now lives in New York City, where she’s a comedy writer for Last Week Tonight with John Oliver.
Her book not only reviews Midwestern expressions, but offers fun tips on hostess gifts, sports talk, travel, shopping, dining, weather and politics, including an ode to the garage fridge and a note on finished basements. By the way, she had neither during childhood.
“I was deprived of those two Midwestern birthrights, and who can say if that’s not what the whole book is about,” she quips.
The idea for the book actually began several years ago while she was sitting in the Leawood Roasterie Café attempting to write a short humor piece. She overheard a woman being described as a character. That means something very specific, she thought. That means the woman is absolutely out of her mind. When she wrote down the phrase, it triggered a deluge of other sayings which later were published on McSweeney’s humor site.
Encouraged by her mom, artist and author Becky Blades, the piece evolved into a book proposal, and in April she celebrated the launch of her book at a Crossroads comedy club. Friends, former school teachers and local dignitaries showed up, including Mayor Quinton Lucas.
The first time Phillips realized the Midwest is sometimes looked at dismissively and inaccurately was when she attended an event at Harvard, where she earned a degree in English and the dramatic arts. A dean began talking slower to her, she swears, after learning she was from Missouri. Another wakeup call occurred at a New York coffee shop. With her normal, bubbly personality in gear, she greeted a barista with “Hi, good morning!” He looked terrified, she remembers, like she had some type of ulterior motive.
Still, she loves New York at its hustling, bustling and walkable best. “It operates at my pace,” she says. “There’s such a rich, cultural diversity, it’s like a thousand different cities put together in a few square miles. And I love the comedy writing community.”
Phillips married a man from Colombia who writes comedy for The Late Show with Stephen Colbert. Their jobs are both on hold until the Writers Guild of America strike is settled, and last weekend she was in Kansas City to celebrate Father’s Day and the birthday of her dad, Cary Phillips. She also traveled to Mizzou in Columbia to present a workshop at the Missouri Scholars Academy. She enrolled in this short-term program while in high school, where she played competitive basketball, performed on stage and excelled in trivia. At college she continued acting, singing, stage managing, costume designing and producing plays, but eventually felt called to be a writer.
“My first love is musical theater,” says Phillips. “I’m good enough at it to know that I’m not good enough to do it at the highest level. I realized I could do more and be in more places as a writer.”
Last fall Phillips won an Emmy Award for her work on the John Oliver show, which she joined in February 2022. Before that she worked at various ad agencies, tutored kids, published freelance pieces, did standup comedy and developed a comedy game show called “Citizenship LIVE!” with her husband. She also endured more than a dozen rejections from other shows, a situation made tolerable by having watched her parents go fearlessly through huge job changes while she lived at home.
Does she still remember her roots and use some of the phrases in her book? “Yes, 100 percent. I say Midwestern stuff all the time,” Phillips confirms.
She says there’s been a bit of a status quo shift and observes the Midwest is having a moment. Many people cling to any connection they can establish with the middle of the country, lately popularized by TV series like Ted Lasso and Somebody, Somewhere.
“Those shows are both so accurate and full of heart without feeling pandering. That’s something I hope my book accomplishes.”
Phillips sold the idea for her book during Covid and took a road trip through many cities for research. She has nice things to say about each of the dozen states she includes, but admits that Missouri and her hometown have a special place in her heart.
“I love exploring all the new cool spots, because it’s changed so much since I left in 2011,” she says. “I love driving around, singing in the car and having so much space. And I love the barbeque.”
In the book’s last sentence she offers this final acknowledgment: “Kansas City, I made this for you, thanks for making me.”