Kansas Citian won Emmy for comedy writing. Next: Her guide to how funny the Midwest is

Taylor Kay Phillips is now an Emmy-winning writer on HBO’s “Last Week Tonight With John Oliver,” but just a year ago she was still collecting rejection letters from late-night shows she’d applied to.

It was a practice she started early growing up in Kansas City, and she credits her father, Cary Phillips, with helping her gain proper perspective.

“I auditioned for Starlight (Theatre) and never ended up in shows there,” Phillips, 29, recalls. “They had a children’s chorus audition when I was 9 and they sent a rejection letter, a physical rejection letter, to my house. And my father said, ‘Oh my gosh, it’s here, we have to frame it! This is the first one!’ That was my family’s attitude toward rejection: It means you’re trying, the idea of being in the arena. … It doesn’t mean that rejections aren’t allowed to hurt — there was always a safe place to be sad about it — but there was pride to take in the idea of continuing to be out there.”

Phillips has been out there plugging away ever since.

She was hired earlier this year as a writer on “Last Week Tonight” (airing 10 p.m. Sundays and streaming on HBO Max). And, never forgetting her Kansas City roots, she has a book coming out next spring, “A Guide to Midwestern Conversation.” (More on that below.)

Helping to script John Oliver’s topical weekly show requires writers do more than simply pitch jokes.

“I love the learning that we get to do on the show just by virtue of being a part of it,” Phillips says. “We learn so much about these topics and we get the benefit of that immediate release where we get to say something and it can be irreverent. In fact, it should be irreverent.”

It’s the job of all late-night writers to learn to write in the voice of the show’s star, but that doesn’t mean foregoing their own instincts.

“The proudest moments that I have and the most gratifying are when the joke that I would tell and the joke that would come out of John’s mouth are the same,” Phillips says. “It’s just really fun to feel like you’re still connected to your own comedic voice even when the person saying the things that you write is very, very much not you.”

“Last Week Tonight” is particularly secretive among late-night shows when it comes to divulging how the comedy sausage gets made, but she notes Oliver has said main stories each week are usually the culmination of six weeks’ worth of work.

“The deep dives on the topic are sometimes really fruitful for joke writing, because you’ve spent a lot of time in the world of this topic,” Phillips says, which encourages the show’s writers to dig deeper for less-mined jokes. For instance, a photo of Leonardo DiCaprio on screen may set viewers up to expect a joke about the actor dating 24-year-olds, but it’s incumbent upon the “Last Week Tonight” writers to do better. “When you’re looking at it for the umpteenth time, that’s when you say, what’s on the wall behind that guy? You want to give (the audience) something that surprises them.”

Going to the Emmy Awards

Due to COVID-19, “Last Week Tonight” writers work from home and collaborate online, so Phillips “saw Oliver’s legs for the first time” at the Primetime Emmy Awards in September. A week prior, she and her husband, “Late Show With Stephen Colbert” writer Felipe Torres Medina, attended the Creative Arts Emmy Awards, where both were nominees. Phillips won as part of the writing team for “Last Week Tonight.”

“It felt like a very cool, special thing that also felt a little bit fake. Not that the people were fake, nothing like that,” Phillips says, but she kept expecting someone to yell, “Cut! Excellent job performing glamour, but you’re a comedy writer, please put on your sweats and go back to your room!”

Attending the Creative Arts Emmys ceremony also took Phillips back to her Kansas City youth playing basketball, though not in a good way.

“I was debating whether to tell you this but I am: My heels were too high and I fell in the lobby of the Creative Arts Emmys. Twice!” she says. “So I took them off and everything from there on — accepting the Emmy, doing press, taking pictures — I was fully barefoot. But then the swelling didn’t go down.”

Phillips went to a Los Angeles podiatrist who determined she sprained her ankle and, oh by the way, when she thought she sprained her ankle playing basketball in high school, she actually broke it and there’s a piece of bone hanging off her ankle.

“It made me feel better because it’s not just that I can’t walk in heels,” Phillips says. “It’s not that I am completely incapable of any type of glamour whatsoever.”

Phillips played basketball for 12 years growing up in Kansas City. A 2011 graduate of The Barstow School, located in walking distance from her south Kansas City childhood home, Phillips decided by her sophomore year she wasn’t going to try to get recruited to play basketball in college “which came partially from realizing that there were people who felt about sports the way that I felt about performing and writing. And partially it came from not growing anymore and I would have had to change positions. I did not want to be a college point guard, not even a little bit.”

Phillips leaned into her performing arts interests, which had been there all along, beginning with her involvement with Overland Park’s Theatre of the Imagination since second grade. She also read books written by comic actors Mindy Kaling and Tina Fey, learning that “everyone’s path to the job that I have is so individual. There really is no one track.”

At Harvard, Phillips majored in English, with a minor in dramatic arts. She wasn’t a Harvard Lampoon writer, instead focusing on musical theater productions.

“I knew I was not good enough at musical theater to do it at the highest level, so I was, like, ‘This is gonna be the last time I’m able to do this,’ so I put a lot of my heart and my energy into that and I’m very, very glad that I did,” Phillips says.

Launching a career

In 2015 after graduating from Harvard, Phillips moved to New York — at age 10 after a trip to 30 Rock, she promised herself she’d someday live in NYC — and eventually worked in advertising while taking comedy classes at night (where she met her husband in 2016) and writing on the side for respected publications (The New Yorker, McSweeney’s).

She returned home to perform in two original Kansas City Fringe Festival shows: “A Moment of Your Time” in 2015 with her sister, Tessia Phillips (currently based in Seattle and producer for the musical comedy troupe Baby Wants Candy), and a solo show in 2017, “I Can Rap the Raven.”

William Morris literary agent Andrea Blatt, who was one year below Philips during their time at Barstow, reached out to Phillips every six months or so to compliment one of her tweets and then said, “Let me know if you ever have a book idea.”

Phillips did have an idea, an expansion on articles she’d written for McSweeney’s in 2018 where she would take a common phrase and offer the Midwestern subtext. For instance, she wrote, when Midwesterners say “Those kids have a lot of energy,” they really mean: “MONSTERS THEY ARE MONSTERS. I have never once requested compensation for babysitting them.”

Blatt helped Phillips format and refine a book proposal, which they sold to Ten Speed Press in May 2021. The ad agency Phillips was working at let her take a month’s leave to drive around the Midwest last fall doing research for “A Guide to Midwestern Conversation.” It’s due out April 11.

She’s still deeply connected to her hometown, as her Twitter feed reveals, with tweets about the Chiefs, KC Current and the New York City mayor’s sneer that “Kansas doesn’t have a brand.”

For years while she worked her day job, Phillips developed a network in the New York comedy scene and applied for jobs writing for late-night TV shows including “Conan,” “Colbert,” “The Break With Michelle Wolf” and “Game Theory With Bomani Jones.”

Last December she was invited to apply and put together a submission packet for “Last Week Tonight,” a show she had written sample scripts for as a 22-year-old New York newbie taking classes at Upright Citizens Brigade comedy theater.

“That had always been the dream,” says Phillips. She got hired in February, started working on “Last Week Tonight” two weeks later and already has that Emmy to show for it. Phillips keeps her trophy nestled between her husband’s Peabody and WGA (Writers Guild of America) awards (from his writing work on Colbert’s show) “so that combined we have a PEW! Our goal as a couple is to eventually have a PEW! PEW! and the exclamation point is a healthy, happy marriage, of course.”

Phillips says getting to where she is in her career takes hard work but attributes 15% of her success to luck.

“I honestly expected there to be a lot more steps in between an ad job and this job,” Phillips says. “When you’re doing the work, you don’t think, ‘And then one day, I’m gonna get to go to the Emmys!’ You do the work thinking, ‘And then one day I’m gonna get up and my job is going to be to write comedy for the TV.’ And the morning of the Emmys? I did wake up and think, ‘I would like to win an Emmy today,’ but that was the only day that that was the dominant thought instead of ‘I cannot believe that this (comedy-writing career) has happened to me.’”

Freelance writer Rob Owen: RobOwenTV@gmail.com or on Facebook and Twitter as RobOwenTV.

How’s it going, Midwesterners?

“A Guide to Midwestern Conversation” by Taylor Kay Phillips, coming April 11 from Ten Speed Press, offers phrases Midwesterners might say — and what they really mean. A sampling:

▪ “Didja see the game last night?”: We do not have a lot in common, so I am most comfortable in conversations where we are either exchanging opinions about [our hometown team] or recapping their latest performance. I will insist that we go to/watch the next one together. First Bud Light’s on me

▪ “It’s almost time to start decorating for the fall!”: Hold on to your hats. I spend nine months of the year getting ready for these three months. I threw out my child’s baby clothes so I could fill our entire keepsake closet with fall leaf garlands, multicolored gourds, and little stuffed animals that hold up the chalk boards where I write “FALL in love” in perfect calligraphy. (I took a class at the community center!) This is my Olympics. My American Royal. My Grand Finale of Season 243 of The Voice. If I see someone whose home is inadequately ornamented, I will invite them to help themselves to my closet.

▪ “Hey there, how’s it going?”: I want to know how you are doing so that I can respond in an empathetic and appropriate way. Acceptable answers range from “good, thanks!” to “I just lost my uncle to prostate cancer and I’m unsure how to divide his estate with my mentally unstable brother.” Either way, I want to hear about it and offer specific and targeted support and follow up.

▪ “Hi there.”: I am either furious with you or in an incredible hurry. If we ever cross paths again, I will “apologize for being so short before” and give a detailed explanation for my behavior.