In celebration of 20 years of Design Matters, Debbie Millman revisits one of the show’s most endearing traditions—the very first question. For years, she’s opened each conversation with a playful, deeply researched inquiry: something personal, unexpected, and revealing. In this special anniversary episode, listeners will hear some of Debbie’s favorite first questions and the illuminating answers they inspired.
Debbie Millman:
Is it true …
Is it true?
Is it true you have a cat?
You went to college at 15.
You have an entirely black apartment?
Curtis Fox:
From the TED Audio Collective. This is Design Matters with Debbie Millman. On Design Matters, Debbie talks with some of the most creative people in the world about what they do, how they got to be who they are, and what they’re thinking about and working on. On this episode, in celebration of the 20th anniversary of Design Matters, we’ll hear some of the first questions Debbie has asked over the years and the answers.
Ben Schott:
Yes. Yes, it is.
Chip Kidd:
Okay, so here’s what happened.
Alison Bechdel:
That’s such a perfect first question.
Thomas Kail:
Here we go.
Debbie Millman:
Every podcast has its own particular form. There’s the theme music at the top, the cold open, the host intro, the jokey credits, maybe an Easter egg or two. Just like anything else made by people, podcasts are designed and one of the pleasures of listening is to hear that narrative arc repeated and varied over the course of a season, or in the case of Design Matters many, many seasons. Yet sometimes, when a podcast has been around for more than a minute, its form inevitably starts to change organically. I’m not quite sure exactly when I began doing this, but for a long time now, I’ve been starting each interview with a playful question. I put a little detail about my guests that I uncovered in my research and build a question all around it.
There are a few reasons why I do this. I try not to ask a question they’ve already responded to in other interviews and already know exactly what to say. I hope it helps them start to relax and realize that, “Maybe we’re going to have a little fun.” I also want to communicate to my guests that I’ve done my research. I’ve not only seen their creative work or their theatrical productions or films and read as many of their books as I can, but I’ve also looked deeply into their lives. I often call this living in my guests’ lives for a few weeks. It’s one of my favorite things about making this podcast.
But it doesn’t always work. Some guests usually guess who haven’t heard the podcast before and don’t know what to make of an off-topic, rather random question right out of the box. Some guests get a little irritated or just give me a perfunctory answer. And then Curtis, my editor and producer, will likely cut that out in the interview you hear, begins with my second more conventional question. But most of the time, it’s a wonderful icebreaker and it sets the stage for a more candid, freewheeling conversation. On this episode, I’m going to play some of those first questions from the past 20 years.
I’m going to play my question and my guests’ answers. But just for the fun of it, I’m not going to tell you who my guest is until after you hear their answers. Some of them are quite famous and you might recognize their voices. Others may be a little bit harder to recognize unless you pick up a telling detail from our conversation. Good luck and happy listening. Here’s guest number one.
I understand that you have a bookshelf in your house that is so high you use a harness in order to be able to reach the books at the tippy top. Really a harness?
Erik Spiekemann:
Yeah. That sounds like bad planning, doesn’t it? No, but it was intentional. We have two floors and they don’t quite … The seating of the one doesn’t quite go all the way, so there’s a bit of airspace above the one of the desk, and so obviously, there’s bookshelves because you’re going to never have enough bookshelves, half of my books are sitting in cellars and warehouses anyway. And we tried all sorts of ladders and things and it never quite worked because ladders take space and then you’re too far away and you are about to fall. So we got this climber harness and I have a little remote control that I sit there and go up and down.
It looks ridiculous, but it actually works. And the best thing is being halfway up there in midair and you always find books that you weren’t looking for and then you always end up reading them for two hours.
Debbie Millman:
Sitting up there-
Erik Spiekemann:
It’s brilliant.
Debbie Millman:
… midair in the harness.
Erik Spiekemann:
Yeah, I think it’s a bit of a feeling that kids used to have when we used to have tree houses and stuff. You are away from it all. Nobody can get to you. Except when you drop the remote, then it becomes a little embarrassing, but it hasn’t happened so far.
Debbie Millman:
Okay. If you guessed who that was, you’re likely a fan of typography because that man now suspended in our minds in a harness in his library was none other than Erik Spiekermann. He’s a German typographer, designer and writer and I interviewed him in 2012. Next up, mystery guest, number two. If you are a regular design podcast listener, there’s a good chance you’re going to recognize this voice.
Is it true that you went to college at 15 to study population genetics with a specialty in corn?
Roman Mars:
It’s not true that I went to college to study population genetics. I went to college at 15-
Debbie Millman:
To study corn?
Roman Mars:
That is true, but I just went to be in college. I wanted to be in college very badly and then I always wanted to do science. And later on, I found genetics and it just so happened that the specialist who studied genetics at Oberlin was a plant biologist, so I began to study plants and then I went to try to get my PhD in plant population genetics after that. And then I discovered transposable elements in maze and then that was it.
Debbie Millman:
It hooked you. So was Doogie Howser originally based on you?
Roman Mars:
No, no, not at all. Doogie Howser predates me.
Debbie Millman:
So why were you so desperate to go to college at 15?
Roman Mars:
High school and the normal way things were in my life where it was not something, I wasn’t really into it, but I loved learning stuff and I love reading and I love all that sort of stuff. But for some reason, I was one of these kids that from age 10 on was researching colleges of places I wanted to go, and for some reason, I just had in my head that college was the place I would be happiest and I was totally right. I was. In fact, I was so happy with it I decided to go to grad school, even though I didn’t finish grad school, but I wanted to just keep going to college essentially.
Debbie Millman:
That, listeners, was Roman Mars, the creator and host of the long-running design podcast, 99% Invisible. I interviewed him way back in 2012. Okay. Number three.
Is it true you have a cat named Olivia Benson?
Jessica Hische:
Well, we named her Olive. Her original name was Buttons, which she’s just was such a mean cat when we adopted her that we thought it would be just too ironic to keep it at Buttons. So Olive seemed the most appropriate black cat name, but because I’m a crazy, crazy Law & Order SVU fan in terms of watching it while I work, I casually call her Olivia Benson and now Russ, my fiance, has adopted it as her official name as well.
Debbie Millman:
I love it. I just recently became a Law & Order SVU person and I also have a crazy mad crush on Olivia Benson. So when I saw that that’s what you called your cat, I had to ask, what is it about Olivia Benson that you love so much?
Jessica Hische:
Well, she’s hard as nails-
Debbie Millman:
Yes, she is.
Jessica Hische:
… but still looks good in a pantsuit. She always has great hair. Yeah, she’s fantastic. She really is. So in any case-
Debbie Millman:
That was designer, illustrator, lettering artist and type designer Jessica Hische in 2011. She’s now my good friend and practically my little sister guest number four, hint, she’s a many-time Caldecott medalist.
So the first question I want to ask you is this, is it true that you love drawing animals but are ashamed to say that you almost always want to put clothes on them?
Sophie Blackall:
Oh, that is true and I’m only mildly ashamed of it because I think they look better with clothes most of the time.
Debbie Millman:
So what’s wrong with wanting them dressed? I think that’s absolutely appropriate.
Sophie Blackall:
Oh, it’s probably not really taking their needs into consideration, I have to admit, but like children. You have children to entertain yourself. So up until an age when they can refuse, you can dress them in amusing outfits, the same as with animals.
Debbie Millman:
I always feel a little bit guilty when I dress my pets up. I feel like Scruffy, my older dog, feels that it’s somehow undignified and he always gives me that look like, “Really again?”
Sophie Blackall:
Yes, I dream of having a donkey because I think a hat would obviously be really good on a donkey, but if I have a donkey, then I want a goat to stand on the donkey’s back. And then I need a rooster who will be compliant enough to stand on the goat’s back and that whole thing is going to teeter and then you have to care for them the rest of the time, which is just too much bother.
Debbie Millman:
Well, most of the Warner Brothers characters are animals that have some type of attire. In fact, many, many, many years ago … I thought you’d enjoy knowing this. Many years ago I worked on a project with Bugs Bunny and inadvertently had him dressed in just a jacket, but no bottoms.
Sophie Blackall:
No pants, no.
Debbie Millman:
And apparently, we were told that Bugs is never bottomless. I never knew that.
Sophie Blackall:
Yeah, when you get into those kinds of details, then just Bugs have paws that can facilitate opening buttons and flies and things to take the trousers off and you can really paint yourself into a corner. I do, in my defense, putting clothes on animals. My one rule is that they should stay more or less in the way that an animal would move and that the clothes should be ill-fitting in the way that they would be if you were to actually put them on that animal.
Debbie Millman:
Okay, well-
Sophie Blackall:
That makes it all okay.
Debbie Millman:
And I agree.
That was artist, author and illustrator, Sophie Blackall. Her books include If We Were Dogs and Ahoy. In Sophie’s case, you can judge a book by its cover because the covers feature her beautiful drawings. They’re really, really stunning. All right, we’re up to guest number five.
Last year you spoke at the TED Conference and rocked the house with your brilliantly funny presentation. And when I watched your talk, I couldn’t help but notice you wearing some really funky glasses. They only looked like they had half a frame.
Chip Kidd:
Right.
Debbie Millman:
So where can you get these glasses? Is it a whole new fashion statement you’re trying to make?
Chip Kidd:
Okay, so here’s what happened.
Debbie Millman:
Ooh, getting a story.
Chip Kidd:
I had the glasses and they were like my signature glasses. I called them my Robin mask. And so two weeks before I’m supposed to go on a TED, a certain person I love sat on them and broke off the right temple. They were custom-made in England and there was no way it was going to get fixed in time. But what I found was the design of the glasses was such that they could sit on your face and still hold up. You actually didn’t need the right temple for them to stay on your head. So I thought, “Well, that will be interesting. I’ll go on TED and half my glasses will be missing and people will think that’s weird, but maybe they won’t notice because the glasses will be perfectly straight, okay?” PS, my name for my TED talk is the 19 most terrifying minutes of my life. That’s what it should have been called.
Debbie Millman:
Was it really the most terrifying 19 minutes?
Chip Kidd:
Well, it was like having a colonoscopy in that the preparation was far worse than the actual thing, but the preparation was excruciating.
Debbie Millman:
So tell us about the glasses and then tell us about the preparation.
Chip Kidd:
All right, so two minutes before I’m about to go on live Ted streaming all over the world and there’s Jeff Bezos in the audience and Al Gore, that’s when they clamped on the Lady Gaga skank mic, which I referred to right away.
Debbie Millman:
Yes, you did.
Chip Kidd:
And that threw everything off and it screwed the glasses up completely, made them tilt because it was supposed to rest on both temples of the glasses and it only had the one, as if I needed one more reason to panic.
Debbie Millman:
Were you ready to throw up?
Chip Kidd:
No. I had taken enough medication at that point that I couldn’t have thrown up even if I wanted to, but I thought if people think I did it on purpose, so much the better and why would they think otherwise?
Debbie Millman:
Of course, you’re so stylish. I wish our listeners could see you in the studio today with your striped socks and plaid shoes and you’re just divine.
Chip Kidd:
Oh, please, it’s fall.
Debbie Millman:
That was none other than Chip Kidd, legendary book designer and writer extraordinaire. I’ve had Chip on my show many times over the years. This interview took place in 2013. All right, we’re just getting warmed up here. If you’re keeping score, this is guest number six.
Is it true that the first job you got after graduating college was as a letter writer for a porn magazine?
Susan Szenasy:
Well, yes. Would you like me to detail that one?
Debbie Millman:
Please, indeed.
Susan Szenasy:
Well, it was actually a job that I accepted, but then I resigned on my way back to New Jersey where I lived at the time because I couldn’t stand the idea of doing that kind of work. Since the job itself was based on a lie because I mean, aren’t the readers supposed to be writing those letters? So I would be writing those letters for these articles that I didn’t want to read, but this was a very desperate time. There was a recession. I wanted publishing, I wanted to be in magazines, and I did accept it, but then I resigned it before I started.
Debbie Millman:
Even before the first day?
Susan Szenasy:
Yes.
Debbie Millman:
That was Susan Szenasy, who in spite of that rough start, went on to have a pioneering career as a magazine editor and who has also written several books about design. We spoke in 2013. Guest number seven. No hints here, but he has a very recognizable accent.
So in addition to all the vocations that I just shared with our listeners, is it true that you also play drums in a funk band?
Ben Schott:
Yes. Yes, it is. I know it seems incredibly unlikely, even I think it’s quite unlikely.
Debbie Millman:
How did that happen and what do you play? What do you do with this funk band?
Ben Schott:
I haven’t played for years, although I was recently at an event and there was some musicians on a stage and they were playing. And after about half an hour, one of them lent into the mic and said, “Does anyone here play the drums?” Now, if there’s any drummers listening, you have dreams about this happening. So I looked around and I was like, “I speak a little jive.” So I got up and I played the drums and a lot of my friends who were there had no idea I played. I think I was wearing a tweed suit and it was just, “Who was the crazy limey on the drums?”
Debbie Millman:
And was it respectable?
Ben Schott:
It was average white drumming from an average white drummer.
Debbie Millman:
From an average white limey drummer.
Ben Schott:
Yeah, not quite good enough for the average white band, but yeah, it was up there as perfectly mediocre.
Debbie Millman:
The drummer is Ben Schott, author of the Schott’s Miscellanies and Schott’s Almanac series. I interviewed him in 2016.
Guest number eight, here’s a hint, he’s an old friend of mine, he dresses really well and he’s also dressed me a few times.
Isaac Mizrahi:
So great to be here.
Debbie Millman:
So good to see you.
Isaac Mizrahi:
Well, I should start by saying I’ve known you for a long time and you’re a couple of things too.
Debbie Millman:
Well, what can you say?
Isaac Mizrahi:
You’re not a slob, okay?
Debbie Millman:
Well, so really you’re a slob?
Isaac Mizrahi:
Yeah, I guess you could call me a … I do have my slovenly moments. Yeah.
Debbie Millman:
Now I don’t ever remember seeing you slovenly. Your apartment has always been gorgeous as far as I can remember.
Isaac Mizrahi:
Well, it’s like that Shakespearean thing where someone who’s so evil also has a really pure beautiful side and vice versa. Yeah, I am a complete organization, neat freak, but on the other side of that, I can go for days with just lying in the same spot, getting bedsores, watching Real Housewives marathons.
Debbie Millman:
Oh my God, me too True. And I’m an obsessive compulsive organizer.
Isaac Mizrahi:
Yeah, so everyone has their moments.
Debbie Millman:
Yeah, yeah. Wow.
Isaac Mizrahi:
I think that’s healthy, don’t you?
Debbie Millman:
I’d like to think so.
Isaac Mizrahi:
And I will go further, I’m not kidding, this is a theory that I have, I think that it’s in those times that really stylish people are at their most stylish. How about that?
Debbie Millman:
Oh, I love that.
Isaac Mizrahi:
I know that’s the truth because that’s who you really are. So it isn’t the way you wear your couture, like Alexander McQueen gown with hair that you get done by Garen before you go. That’s easy, right? It’s when you’re actually being a slob in bed watching the Housewives if you have the impulse to put lipstick on and I don’t know what little furry slippers that are cute. Seriously, that’s when you are your most stylish.
Debbie Millman:
Well, I do have a really nice pair of Vera Wang pajama bottoms that I live in.
Isaac Mizrahi:
You see what I’m saying? Yes.
Debbie Millman:
I’d like to think that that makes me stylish, but there are times when I realize that I haven’t gotten out of Vera Wang pajama bottoms since Friday and it’s Sunday night.
Isaac Mizrahi:
Well, not to belabor the point, but my hair takes on incredibly chic perukes, 18th-century powdered wig-ish forms when I’m in bed for that long.
Debbie Millman:
Yes. Mine takes on epic proportions.
Isaac Mizrahi:
I think are fabulous. And I want to stop everything and hire Stephen Mizell to come and take my picture at that moment.
Debbie Millman:
Call me and I’ll come and do it for you.
Isaac Mizrahi:
Okay.
Debbie Millman:
That was fashion designer, actor and performer Isaac Mizrahi who joined me on Design Matters in 2016. Guest number nine, hint, one of her books is likely in your kitchen.
I understand you’ve been passionate about food since before you can remember I read that you were scrambling eggs in pre-kindergarten, making Thanksgiving dinner at the age of 12, and when you were about five or six, you gave your first cooking class to your great-grandmother, Nanny, and her friends in North Miami.
Julia Turshen:
This is very accurate.
Debbie Millman:
All true? Wow.
Julia Turshen:
All true. There’s a picture, I’ll have to send it to you, of me demonstrating the fruit salad because I thought maybe they don’t know how to do that.
Debbie Millman:
So that was the lesson you were making, teaching the great-grandmothers how to make fruit salad.
Julia Turshen:
My great-grandmother, who I was very lucky to know for the very early part of my life, she lived in this hysterical apartment building in North Miami Beach with all of her friends and they were all in different apartments. And so when … I have an older brother, and when we would visit or my cousins or anyone, the whole thing was you would give a demonstration to Nanny and her friends and I think all grandchildren and great-grandchildren would do that. And so most people would sing a song they knew at camp or something, or for me, it was how to make fruit salad.
Debbie Millman:
And was there a special recipe to the fruit salad? Anything exotic?
Julia Turshen:
I think it was like a technique. I think maybe there was a melon ball or I’m not really sure, but I have to look.
Debbie Millman:
And is it also true that you have a tattoo of a loaf of bread?
Julia Turshen:
That is true.
Debbie Millman:
And where do you have it?
Julia Turshen:
Yeah, it’s right. I can show it to you. It’s not in a weird place. It’s right on my-
Debbie Millman:
Oh, very nice.
Julia Turshen:
What do you call this? My forearm?
Debbie Millman:
Your forearm, right by the crook of your arm, right?
Julia Turshen:
Mm-hmm. It’s often mistaken for a mailbox, but it’s okay.
Debbie Millman:
That was food writer and cookbook author Julia Turshen. Julia’s books include Simply Julia: 110 Easy Recipes for Healthy Comfort Food. I spoke to her in 2015, 10 years ago. Well, we’ve still got a lot of ground to cover, so stay with me. If you’ve guessed three of the preceding nine guests, you’re batting .333, which as baseball fans know is really good. I’d say you’re on your way to a very successful listening experience because this was hard even for me and I did the original interviews.
Guess number 10, lots of hints are dropped in the Q&A itself.
I understand that you grew up in Belfast in Northern Ireland and went to a school that you’ve described as kind of rough. What does kind of rough mean exactly?
Oliver Jeffers:
Well, kind of rough means that it was filled with the sort of kids who were being kicked out of all the other schools for various sorts of offenses.
Debbie Millman:
Were you one of those kids?
Oliver Jeffers:
No, I wasn’t one of those kids. It’s actually at this … I mean, I’m talking, there’s serious criminals, went through the doors of that school. Most of the kids were fantastic, were great and they were there because their parents were interested in opening their minds by exposing them to people who were either Catholic or Protestant, whichever religion they were not because most other kids who go to school in Northern Ireland don’t come across somebody of the other religion if they go to college. It was a little rough around the edges, but I learned how to talk my way out of trouble pretty quickly.
Debbie Millman:
How did you do that?
Oliver Jeffers:
Well, first of all, some of the people in my group of friends were of the toughest variety. And yeah, it’s because I could draw. That went both for me and against me. It went against me in that I showed interest in an academic subject and that wasn’t cool, but it went for me because the bigger, tougher kids were interested in having me draw on their school bags or under their skateboards. So it went for me in that sense.
Debbie Millman:
And what kind of things did you draw under the skateboards?
Oliver Jeffers:
Whatever the hell they told me to, really. I would just make things up. I would make characters up, the names of their favorite bands, just whatever it was really.
Debbie Millman:
That was illustrator, artist, designer, and author, a true polymath, Oliver Jeffers whose many picture books include How to Catch a Star and The Moose Belongs to Me. I’ve interviewed him several times over the years. What you just heard was an interview in 2015.
Guest number 11. If you read the New Yorker magazine, you’ll have seen her work in practically every issue going back several decades.
Let’s begin back in 1940 when an overhead light bulb in your parents’ apartment burned out, and in many ways, your family story begins then. Can you share the story of the bulb and your almost sister?
Roz Chast:
This is a story that, of course, I was not there for but-
Debbie Millman:
Far younger than that.
Roz Chast:
Younger, yeah. But it was a story that I heard repeated many times because I think it had a lot of meaning for both of my parents. My father was … I have a lot of phobias, but he is sort of my phobias to the next exponential power. And one of his many phobias was changing light bulbs and also getting up on a ladder and some high light bulb burned out. And my mother, who was pregnant at the time with my almost sister, climbed up on the ladder to change this light bulb because he could do neither of those things and she hemorrhaged and lost the baby. I was told the story several times. I’ve also been told by various doctors that there was no way that climbing up on a ladder and changing a light bulb causes you to lose a baby, but-
Debbie Millman:
So there was no correlation.
Roz Chast:
There was no correlation, whatsoever. The baby lived for a couple of days and she was about seven and a half months pregnant. So it was pretty traumatic. My mother almost died. Really nothing good came out of it at all. I think it was pretty horrible for both of them. And they didn’t want to have another child for a very, very long time. They waited almost 15 years to have me, by which point they were considerably older than most people’s parents back then.
Debbie Millman:
And you were made fun of because of that.
Roz Chast:
It wasn’t simple making fun. It was like making fun plus the terror of being told by your schoolmates, “Not only are your parents old, but that means that they’re going to die really soon,” which I had guessed anyway, but this was like, “No, you’re actually not wrong about that.”
Debbie Millman:
But they were because they lived for a very long time. Your mother lived until she was 97 years old.
Roz Chast:
Yes, she did. She did.
Debbie Millman:
Yup, you are correct. That was the award-winning cartoonist, Roz Chast, who joined me on the podcast in 2016 to talk about her illustrated memoir, Can’t We Talk About Something More Pleasant? All right, now here’s guest number 12.
I understand that one of your all-time favorite Mad Magazine cartoons began with a first grader’s “What I Did Last Summer” report about visiting a farm and seeing pigs. Why is this your favorite?
Alison Bechdel:
That’s such a perfect first question because it ties in with the work and life being the same thing. So this little boy writes “What I Did This Summer” report about going to a farm and seeing pigs and it evolves over the years. For every school paper, he rewrites a version of this until he’s an animal husbandry student and he’s writing scientific papers about pigs and these same little throughlines keep showing up.
What excited me about it was this idea that there’s just one thing that you’re passionate about and you can just keep doing it for the rest of your life.
Debbie Millman:
Over and over.
Alison Bechdel:
Over and over on a slightly higher level each time, hopefully.
Debbie Millman:
Hopefully.
That was graphic novelist and MacArthur fellow, Alison Bechdel, author of Fun Home and Are You My Mother? from 2016. Okay, here’s guest number 13.
Is it true you have an entirely black apartment?
Cindy Gallop:
Not anymore.
Debbie Millman:
Oh, it isn’t true. So tell, tell, do tell.
Cindy Gallop:
So it used to be true in that for 10 years I lived in the black apartment and it was indeed all black because my overall brief to the designers of it was, “When night falls, I want to feel like I’m in a bar in Shanghai,” Shanghai being one of my favorite cities and The Glamour Bar in Shanghai, which is no longer unfortunately open, being one of my favorite bars in the world. And the designers came back and said, “Here’s our vision for that. All wall, ceiling, floor, carpet, everything, all black,” and I went, “Oh.” And they said, “No, no, it’s large enough to take it. We’ll paint it gloss black and we’ll light it so the light reflects off the paint so it’s not oppressive and it will make all your art and belongings really pop.” And it totally did because people would visit me and they would have no idea I lived in all-black apartment until I told them.
So that was great. But I actually sold the black apartment last year and I bought instead the sky apartment. And the sky apartment like the black apartment is a complete fixer-upper because the black apartment was 3,800 square feet of raw space in the old YMCA on West 23rd. In fact, the fun thing about that was I bought the front half of the sixth floor of the Y, which is where the Y used to have the indoor pool in the back half. So my apartment was the men’s locker and shower rooms at the YMCA.
Debbie Millman:
I love that, Cindy.
Cindy Gallop:
I literally live where village people wrote the song about. So I wanted to find somewhere equally fun to live in. So I totally lucked out because I found a triplex penthouse on 5th Avenue with three terraces, amazing views and huge amounts of outdoor space that had not been touched in 30 years and was being lived in by a hoarder. Bargain. So we’re good.
Debbie Millman:
Fabulous.
That was from my 2016 interview with Cindy Gallop, who has made her remarkable career in advertising, marketing and branding and who founded the Pioneering website Make Love Not Porn.
Okay, we’re now up to guest number 14.
Is it true that when you were growing up in Northern Virginia-
Thomas Kail:
Here we go.
Debbie Millman:
… the first song you ever memorized was Slick Rick’s rap, “Mona Lisa”?
Thomas Kail:
Absolutely.
Debbie Millman:
Okay, prove it to me.
Thomas Kail:
It’s not going to be that pod, but let’s just say it’s in a very special place in my brain that does not go away, which is what I was always fascinated by with lyrics. Where do they go? Somehow they get lodged in. And I remember someone giving me that tape and then it was put into my brain and it’s still there and that song can come on and it just emerges. I don’t know where it’s been for six months or two years and that song was really important to me. And those bus rides into Lyles-Crouch Elementary school were very important.
Debbie Millman:
Well, I know that your bus driver’s musical taste had a lot of impact on you. What kind of music was he playing?
Thomas Kail:
Everything. And you’re so informed. I’m in the middle of two sisters, which basically defines everything about me, so-
Debbie Millman:
Nice.
Thomas Kail:
… you’ll find that out very quickly.
Debbie Millman:
Yeah, absolutely.
Thomas Kail:
And so the people that you ride with until you are able to drive often dictate a lot of the music and a lot of the input that you’re going to have, where the conversation’s going, what we’re going to be talking about is defined just like it is, “Let me change the radio station.” I wasn’t allowed to touch the radio on the bus, so whatever he was listening to is what we all were listening to. And that becomes a stand-in for an older sibling. So then when I started driving into school, when I was still a passenger with my older sister, it was whatever she wanted. There was no say or my dad did. That’s where I fell in love with the ’60s and that’s where I fell in love with the Beatles and had an understanding of what that was.
So I was very much shaped by those earlier car rides. I think most good things in my life probably happened during a car ride.
Debbie Millman:
I read that the clarity and the precision of the storytelling and the economy of the words and language of Slick Rick’s “Mona Lisa” really opened your mind up. And I wanted to know how, in what way?
Thomas Kail:
Well, the storytelling, it’s like poetry. There’s so much that’s compressed and so I was fascinated by that. And also in that song, Slick Rick plays different characters. That was new to me, that a song could be a sketch or a small play. And I think that was really striking when he did the voice of the other per … It was like, “Oh, there’s a conversation happening. It’s not just coming from one place.” And so that was instructive and I filed it away until it eventually came out in my 20s and I was like, “Oh, maybe I should do this for a living.”
Debbie Millman:
He did end up doing it for a living. Dear listeners, that is Thomas Kail, the director of the Broadway hit musicals, Hamilton and In The Heights, among many other plays and television shows. I spoke to him in 2017. So how many guests have you guessed correctly so far? If you’re striking out, I’m going to throw you a softball. This is your last chance, guest number 15.
I understand that in your high school yearbook, there’s a note from a girl who wrote, “I Like You,” even though you are very mean. So were you really mean in high school?
Roxane Gay:
What? I have no idea what you’re talking about. Yes. No, I wasn’t. I was really shy and awkward, but apparently, my memory of myself and people’s memories of me are very different things. And I do remember, probably in my sophomore year or so, I developed a mean streak. And it wasn’t bullying or anything like that, but if I had something biting to say, I said it. I had no filter.
Debbie Millman:
Do you remember any of the more biting things you might have done?
Roxane Gay:
No, I don’t. Thank God. I have absolved myself of all of those sins conveniently, so I don’t remember what I said.
Debbie Millman:
Now, you’ve stated that, in many ways, likability is a very elaborate lie, a performance, a code of conduct dictating the proper way to be left to our own devices. Do you think that we’re all really diabolical deep down inside, Roxane?
Roxane Gay:
I hope so. I genuinely hope so. No, I don’t think we’re all diabolical deep down inside, but I think we have imperfections and darknesses inside of us, and some of us are better at hiding them than others. But I never trust anyone who seems perfect and incredibly likeable and incredibly nice. So I always just think, “What’s going on under there?” So all of like the HGTV hosts, anyone who appears in a Hallmark Channel movie.
Debbie Millman:
Kelly Ripa.
Roxane Gay:
Yes, I just think-
Debbie Millman:
No offense to Kelly. We love her.
Roxane Gay:
No, just whenever I see these people in this performance of niceness, I just think, “My God, you are probably the cruelest person alive.” And so I think it’s more healthy when we at least acknowledge those parts of ourselves and I think maturity is knowing when to release that and when not to. And so hopefully, I have, since high school, matured at least a bit.
Debbie Millman:
Except on Twitter.
Roxane Gay:
What?
Debbie Millman:
Okay, I even said her name. So if you didn’t guess correctly, you simply weren’t paying attention. That was writer Roxane Gay from a live interview I did with her at the On Air Fest back in 2019 before she became my wife. In fact, this is when we first went public, so to speak about our new relationship. We’re only up to 2019, but for now, we’re going to let you off the hook, but I love doing this so much, we may have to do another one, just to bring us up to 2025. If you want to hear more than the first questions and answers from these special guests, you can hear the full interviews and hundreds of other interviews with a large variety of guests, designers, performers, musicians and writers on our website, designmattersmedia.com or wherever you get your podcasts.
Next week, we’ll have a new episode, but we’ll be continuing into the fall with more special episodes called From the two decades I’ve been podcasting Design Matters. Yes, this is the 20th year we’ve been podcasting Design Matters, and I’d really like to thank you for listening. And remember, we can talk about making a difference, we can make a difference or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.
Curtis Fox:
Design Matters is produced by the TED Audio Collective, by Curtis Fox Productions. The interviews are usually recorded at the Master’s in Branding program at the School of Visual Arts in New York City, the first and longest-running branding program in the world. The editor-in-chief of Design Matters Media is Emily Weiland.