Amy Sherald-I Painted Michelle Obama

Summary

Toure Show: Amy Sherald – Painting Michelle Obama

Podcast Information

• Title: Toure Show
• Host/Author: DCP Entertainment
• Episode: Amy Sherald - I Painted Michelle Obama
• Release Date: April 6, 2025
• Description: Touré interviews successful individuals to uncover their paths to success and share insights to help listeners on their own journeys.

Summary

1. Introduction to Amy Sherald and Her Achievement The episode opens with Toure expressing his excitement about interviewing Amy Sherald, the renowned portrait painter famous for painting the official portrait of First Lady Michelle Obama, which now hangs in the National Portrait Gallery. Toure highlights Amy's crossover appeal, noting her ability to attract fans beyond the traditional art world due to her inspiring story and multifaceted talents, including her past as a rapper.

2. The Unveiling of Michelle Obama's Portrait Toure recounts a personal anecdote about his mother's initial reaction to the portrait: “The day the paintings were unveiled, my mom called and she said, I don't like the color of Michelle Obama's skin. And I was like, mom, that's what Amy Sherald does” ([00:15]). Amy acknowledges mixed reactions, particularly from within the Black community: “A lot of people did. A lot of, I'd say a lot of black people didn't” ([00:29]).

3. Artistic Choices and Intentions Amy delves into her intentional choice of depicting Michelle Obama's skin tone in gray-black hues. She explains that the selection was mutual and not heavily discussed: “I didn't force that on her. She knew that you were going to give her that gray black” ([00:40]). Amy emphasizes the historical significance of the commission: “These portraits have to be as special as the moment, because they may not ever happen again” ([01:06]).

4. Reception and Impact of Her Work Discussing the reception of her portrait at the National Portrait Gallery, Amy shares the joy of seeing younger audiences engage with her work: “I was really excited to see 5 year olds, 6 year olds, 8 year olds, that they knew who I was and they wanted to take a picture with me” ([05:34]). She highlights the importance of representation and how her work resonates with diverse demographics: “It's relatable, it's reflective. It's loving, it's kind” ([05:45]).

5. The Creative Process and Color Choices Toure and Amy explore her unique approach to color in portrait painting. Amy describes her intuitive process, where colors emerge organically based on the subject and attire: “Everything that I do is intuitive and I don't try to do it. It's just what happens when I make the work” ([07:04]). She likens color description to sensory experiences, illustrating the emotional connections she infuses into her palette: “I think one of the flavors of the yogurt was like, when your cell phone battery is charged” ([07:57]).

6. Addressing Criticism and Cultural Perceptions Amy discusses the varied perceptions of her work, acknowledging that some traditionalists and critics have taken issue with her color choices. She cites instances where her paintings were misunderstood or deemed offensive, despite her intention to celebrate Black identity with dignity and beauty: “We have different ways of seeing ourselves based on how we're seen in the world” ([52:00]).

7. The Michelle Obama Commission Story Amy narrates her journey from winning the National Portrait Gallery Competition to being commissioned to paint Michelle Obama. She recounts her nervousness during the White House meeting: “I was like, Amy, say something... and he walks up to me, he's like, hello, nice to meet you” ([38:51]). The collaborative process with Michelle's stylist over dress choices is detailed, emphasizing the significance of color and pattern in the final portrait: “[...] she was immediately drawn to it because of the patterns on it” ([40:34]).

8. Balancing Art and Personal Life Amy opens up about her personal struggles, including a heart transplant she underwent and her journey towards emotional well-being. She shares how her health challenges have shaped her perspective and artistic expression: “I'm good with my life. Like, if I die tomorrow, I'm still good with my life” ([60:05]). Her candid discussion about fears, responsibilities, and finding love later in life adds depth to her narrative.

9. The Art Business and Industry Insights The conversation shifts to the dynamics of the art industry, particularly the financial aspects of selling paintings through galleries. Amy explains the 50/50 split with galleries like Hauser & Wirth, emphasizing the value galleries provide despite the significant commission: “Industry cut is 50. 50” ([65:44]). She discusses the balance between maintaining artistic integrity and adapting to market demands, noting that her selective production ensures the uniqueness and value of her work: “Scarcity creates value” ([67:29]).

10. Advice for Emerging Artists In her closing remarks, Amy offers heartfelt advice to young portraitists: “You just have to keep working. This will not happen unless you continue to work” ([72:42]). She underscores the importance of perseverance, self-discipline, and staying true to one’s artistic vision despite challenges and setbacks.

Notable Quotes

• Amy Sherald on Representation: “People are hungry to see themselves in ways that they've never seen themselves.” ([05:34])
• Amy Sherald on Color Choices: “It's an emotion attached to it as well.” ([07:57])
• Amy Sherald on Artistic Process: “Everything that I do is intuitive and I don't try to do it. It's just what happens when I make the work.” ([07:04])
• Amy Sherald on Industry Challenges: “Scarcity creates value.” ([67:29])
• Amy Sherald's Advice: “You just have to keep working. This will not happen unless you continue to work.” ([72:42])

Conclusion This episode of the Toure Show provides an in-depth exploration of Amy Sherald's artistic journey, her landmark achievement in painting Michelle Obama, and the personal and professional dynamics that shape her work. Amy's insights into representation, color theory, the art business, and perseverance offer valuable lessons for aspiring artists and listeners alike. Her candid reflections on balancing personal life with creative ambition add a relatable and inspiring dimension to the conversation.

For More Information Visit the Toure Show website: https://www.dcpofficial.com/toureshow

Transcript

[Torre]

The day the paintings were unveiled, my mom called and she said, I don't like the color of Michelle Obama's skin. And I was like, mom, that's what Amy Cheryl does. And she's like, I don't like it.

[Amy Sherald]

A lot. People did. A lot of. I'd say a lot of black people didn't.

[Torre]

Right. So. So take me back to now. I'm conceiving this, and I'm going to go with my skin choice.

[Amy Sherald]

That's why she chose me. I didn't force that on her. She.

[Torre]

She knew that you were going to give her that gray black.

[Amy Sherald]

Absolutely. That's why I.

[Torre]

Did you talk about that choice specifically, or you were like.

[Amy Sherald]

Yeah. It wasn't even a real conversation. It was like, I like your work, and I want you to be the one to paint me. And I'm like, well, this is how I paint. She's like, that's what we want. They chose us for a reason. They chose us because there's, like, this break in history right now.

[Torre]

Yes.

[Amy Sherald]

And everybody needs to know this happened. And these portraits have to be as special as the moment, because they may not ever happen again.

[Torre]

I am so excited for this episode. I've been waiting to do this interview for a year and a half and four. Finally, it's here. My homegirl, Amy Sherrid, is a major league portrait painter who painted the official portrait of the first lady, Michelle Obama. It's hanging in the National Portrait Gallery right now. Before that commission, Amy was a big name in the art world, but now she's a crossover star with fans who weren't even into art that much before. But they love her. They're inspired by her, and with good reason. She's an awesome person, a great painter, and a former rapper. We're gonna get into that. She's gonna rap a little, and it's amazing. Before we go too far, Little Housekeeping. Cause Torre's show is about to go into a new chapter. The Patreon era starts now. We're producing two episodes a week now, dropping on Wednesday and Friday. But the Friday eps will be exclusive to Patreon, so you gotta pay $5 a month to get those Patreon exclusive eps. Coming up on the Patreon side, we're gonna have Sheila E. Joy Bryant, Neil DeGrasse, Tyson, Morris Day, and more. Go to patreon.com torreyshow that's patreon.com torreyshow and you'll be able to get in the Friday Patreon exclusives also starting next week, On Wednesdays, our free listeners will get 30 minutes of my Wednesday interviews, while Patreon listeners will get the full 60 or 70 or 80, however long minutes of the Wednesday shows. Coming up on the Wednesday side, we got David Al Greer, the author Ed Weed Donticott, and a crazy one with Dame Dash. I can't wait for you to hear that. So our Patreon supporters will get the full Friday exclusives and the full 60 minutes of our Wednesday EPS. Our team is growing. There's five people working on the show now. We're ready to give you more. So here it comes. Join [e-mail] Torre show to get the best of Torre show. And if you can join on the $20 tier while it's still open, you get to suggest questions and guests. And if I choose your question, I'll say your name on the show as I ask the question. Speaking of the show, let's get back to today's guest, the incomparable Amy Sherrild, a woman who's a brilliant painter with an amazing sense of color. And we're gonna talk about that and her process and the whole story of how she went to the White House, met with Michelle and Barack and ended up getting the commission of a lifetime not long after she was broke. Amy is also a woman who's walking around with someone else's heart in her body. We're gonna talk about that. And she's also got a new heart, figuratively, by which I mean she's deeply in love for the first time in her life, and she lights up when she talks about it. We're gonna get into all that and more. It's the legendary Amy Sherrid. On to. So is that your last show in Manhattan? And there's this line around the block of, like, especially young black and brown people who many of them seem to have never been to a show before. But, like, the Amy Sherrill show to them is like, this is special. And you have become this sort of icon for a lot of these people who are like, you know, I mean, following the Michelle Obama painting, like, oh, my God, Amy Sherrill. And, like, how is that for you? Cause you feel that, like, there's all these people who are coming into art for me, like, I'm a crossover star for a lot of these people.

[Amy Sherald]

Yeah, I don't feel like it's for me, you know, I didn't know the line was out the door until afterwards.

[Torre]

It was so long.

[Amy Sherald]

And I. Somebody showed me a picture and I'm like, that was downstairs, you know, But I don't feel like it's for me. I feel like it's for the art. It's because people are hungry for it. You know what I mean? They're hungry to see themselves in ways that they've never seen themselves. And I do attribute. I can't. I call it the Michelle Obama effect, because she just has that effect on everybody. People love her and I feel like by default they love me. And I just happen to make great work too, so that just makes it even better.

[Torre]

But I think there's definitely an excitement at seeing a young black woman.

[Amy Sherald]

Yeah, for sure.

[Torre]

Making art and being celebrated for it. And they can understand the art.

[Amy Sherald]

It's relatable, it's reflective.

[Torre]

Yeah.

[Amy Sherald]

It's loving, it's kind. And the vibe that night was all love, you know, for me to see young kids there was like, really special. I think as I was walking around, I was really excited to see 5 year olds, 6 year olds, 8 year olds, that they knew who I was and they wanted to take a picture with me. And those were the most touching moments because, you know, the gallery said, like, we've never had this demographic in our space before. So that was like, probably the first time in the history of Hauser and Worth. And it's a global gallery, so it was a big deal. And it's time. It's time for that kind of stuff. I mean, it's time for us to be in those spaces and. And to feel ownership and to be reflected on walls and see ourselves and receive love back from those images.

[Torre]

I love the work and I wanna talk about the work and really dig into it. And one of the things that really leaps out is the color choices. It is so vibrant and yet not overwhelming. Can you talk about just some of what you're trying to do there?

[Amy Sherald]

Everything that I do is intuitive and I don't try to do it. It's just what happens when I make the work, you know, So I have an image in my head. I try to find the right clothes and then I figure out the background color and then everything kind of builds from there. But, you know, it's hard to explain because, like, now I work with an assistant who helps me, like mixing colors and stuff like that. And the other day I was like, I want this blue, this particular kind of blue. And I can see it in my head, but I can't communicate that color to my assistant to mix. And so she mixes it. I'm like, no, that's not the right color. And so I end up having to do it myself because I'm very, very particular about it. And I can't explain it. I just. I can't explain it. But I don't know whether you watch. Do you watch the Good Place?

[Torre]

Of course. Of course.

[Amy Sherald]

I love the Good Place.

[Torre]

She lives around the corner.

[Amy Sherald]

Are you kidding?

[Torre]

For me. So I see him once in a while.

[Amy Sherald]

Oh, my God, I love him. When they describe color or taste, I think. I think one of the flavors of the yogurt was like, when your cell phone battery is charged. You know what I mean? So, like, everybody knows what that feeling is. And, like, I feel like if I could describe my colors, something like that. You know what I mean? Cause it's an emotion attached to it as well. And I don't think I realized how specific it was until I had to work with somebody to help me. And I say, do this, and they're like, nope, it's something that only I can do.

[Torre]

And yet. So the colors are vibrant, and they really work on the eyes. And yet all the black people are this dark gray, the same color over and over. Why are you doing that?

[Amy Sherald]

You know, that story has changed over the past decade. So it starts off with because I thought it looked cool. It then graduated to five years later, you know, because I'm not walking into the studio with a whole bunch of words in my head. It's like, you make some work, you look back at it, and you have conversations with people, and you're like, you know, that really makes sense. So for me, when I look back, it was because I was, I think, not wanting the work to be marginalized in a way that would corner it into a certain conversation about blackness and identity. And so I think I was struggling with that because I knew I was painting black bodies. And I know black bodies are political. And I know just because they're hanging in museum institutions, that's a political statement in itself. But I didn't want the conversation to be solely about identity. And so I was saying then that subconsciously, I think that's why I was drawn to do that. But for this exhibition, I never have time to read when I'm making work. But I read the first chapter of Kevin Quashi's book, the Sovereignty of Quiet. And I really think that subconsciously, again, that it's really about the. The interiority of who we are. And so we have this codified existence of identity, like how the world consumes us, and then we have our own nuanced selves. And I think that become the it becomes a. Our real selves become a shadow of who we really are because we're constantly bombarded with these images in the media of, like, the bigger idea of who we are as, like, black people, the stereotypes and all that. So I really feel like it's about the interior. And the interior doesn't really have any color. You know, the interior is a different experience. And nobody really knows about our interior life except for us. And we share who we are with each other in these very intimate spaces. And so after reading that, I started to think of it in that way. You know, it's not really a removal of color. It's just about dealing with the insides and the spiritual aspects of who we are versus the. What he calls, like, a public identity. Like, it's our private. Our private selves, if that makes sense.

[Torre]

It does make sense. So what do you just. Overall, what do you think you're saying about black people through the work? I see a lot of dignity.

[Amy Sherald]

Yeah.

[Torre]

A lot of beauty. But what are you trying to convey?

[Amy Sherald]

I think that's it. I mean, I think I grew up looking at images that were like that. That were people in my family, that were my grandmother, that were my great grandmother. And when you look at older photographs, I mean, we're dressed up, you know, like, it's a different kind of feeling. Like, you don't get that same aesthetic in 2020 as you did when you take a photograph in 1935, my mom's age. And so, yeah, and there was a. You know, when we were able to have ourselves photographed, there was a sense of self satisfaction and dignity and, you know, presentation. And I think that's part of what it is. And I think the reason that I ventured into this, these ideas, it's because I felt like there wasn't enough of these kinds of images out there. You know, I felt like everything that I ran into was political. And there was a part of me that was developing as a human being, not as a black person, but just as a human and as a woman who wanted to release myself from race and gender and religion and all those things that we are, you know, that are pushed into our face and we're told who we are. Like, my mom told me who to worship. She told me what my life was gonna be like because I was a black girl. You know, first day of school, she said, this is what they're gonna think of you. This is how you have to act. These are the rules of life for you as a young black person. You know, so you grow up With a lot of heaviness that most kids don't have to deal with. You know what I mean? So my niece is six years old. She. She already knew she was different by six. My friend Dana, her son Josh, he's white. He is 11, and he's like, what is black like? You know what I mean? Like, he's so free in his mind. And, like, Charis has already learned the rules of race, you know, and, you know, she's a young girl. So I wanted to feel free from that, and I wanted to. And maybe this was because, you know, I was on my way to getting a heart transplant, not knowing what my life was gonna be like, living for 10 years, thinking that it could be over in 10 years. But I wanted to get down to the essence of who I really was as a person without all of the noise of that public identity, without all of the reactionary emotions that we have to walk around with every day because it's exhausting. And also without the guilt of feeling like I'm leaving behind my people, you know, because we're, you know, I'm. You have multiple experiences all at the same time, you know what I mean? Based off of, like, what I see on the news, it's like I'm deeply hurt by maybe the death of a young black child. And at the same time, I'm working through my own existential feelings of, like, the privileges that I have because I was able to receive an education and the freedom to kind of self evaluate and search for these answers that are floating around the universe of, like, you know, like, just to be able to ask those kinds of questions and not have to worry about surviving on a daily basis, you know? So I think those paint, my paintings, represent that freedom and that. And if you don't have the capacity in your life to live that way, you can come to that work, you can come to the paintings, and you can find a resting place for a moment. You know what I mean? Everything in your life doesn't have to be about contention. In that moment, you can see a reflection of yourself that speaks to your inner person, if that makes sense.

[Torre]

It is. They are calming. Despite this explosion of color, I get a sense of calm. And I'm just in a communion with a person who's just standing there calm in themselves. Like, they're settled in themselves. They're not stressed, they're not running. So I do see some of what you're talking about. And that communion that I can have of, like, this is not the painful black experience. This is the self care part of it.

[Amy Sherald]

And historical pleasure is okay, you know what I mean? Like, we have to somehow turn that around for our kids. We have to translate that trauma into pleasure and they have to learn that as well. You know what I mean?

[Torre]

What were you told? What was the received wisdom about being black? You talk about your mom telling you this is what it means to be a black girl. Yeah.

[Amy Sherald]

I mean, for us, it was about behavior. You know, my father was one of the only black doctors in the city. So, like, everybody knew who me and my sister, my brother, everybody knew who we were. Going into a kindergarten classroom as the only black child was and as a like self conscious, introverted child was like traumatizing in itself. But you've. It was really just about, like, if you do this, they're gonna look at you this way. Like, if you talk loud in class, they're gonna look at you one way. If another student talks loud in class, they're not gonna react the same way.

[Torre]

Don't perpetuate the stereotypes.

[Amy Sherald]

Right? It's that. I mean, it's like. But then you're like, what's the stereotype? I'm five. Like, I don't. You know what I mean? And so it's. It's really interesting. Cause you.

[Torre]

My dad was like, don't return your library books late. That's what they expect of you.

[Amy Sherald]

Yeah. What? All of that.

[Torre]

Okay.

[Amy Sherald]

All of that.

[Torre]

Don't run in the mall because they'll think you stole something. Like, yeah, okay.

[Amy Sherald]

Everything. And it might have been different for my brother than it was for me because I'm a, you know. Cause I'm a. I was a girl. But yeah, I just became very aware, you know, that every. That I was different.

[Torre]

How much of the work is planned and how much of it is discovered in the midst of working through it?

[Amy Sherald]

I guess the majority of it is planned, but the process of making the photograph is organic. And obviously finding the people is. You could consider that organic too, because I just happen to see people walking around, you know, so if I don't see anybody for two months, then I don't have anybody to paint for two months, you know, because it's. It's. I think the people that I find are the reason why the paintings situation the way they do. Like the reason why they feel the way that they do. There's something that they carry inside of them that I'm able to translate. But their clothes and all of that, I do have clothes that I buy that I would like to use for a painting. And then I have to find the person. So I could have an outfit for a year. And then all of a sudden, I'm like, this person could wear that, and it'd be perfect. Or the person's walking down the street, and I'm like, this person has on the perfect outfit. But color choices and backgrounds are the one thing that I. I think I let happen organically and could change in the process of the painting. If I decide something's not working, then everything changes.

[Torre]

So you start with seeing somebody just randomly and say. Or an outfit.

[Amy Sherald]

Yeah.

[Torre]

And then say, okay, let's shoot that person.

[Amy Sherald]

Yeah.

[Torre]

Do they come to the studio, or can you just do it on the street?

[Amy Sherald]

They come to the studio.

[Torre]

So you speak to them and say, yeah.

[Amy Sherald]

I'm like, hey. So, you know, I know this is weird, but this is. I would like to paint you. This is my website. It'll only take an hour. I try to, like, you know, let them know it's not gonna take a long time. You'll get, like, this much money for it.

[Torre]

Are people more saying, oh, I know who you are, or is it still like, hi, I'm Amy Sherrill. I'm not weird. I'm an actual. I'm a painter.

[Amy Sherald]

You can tr. It depends. Sometimes they know who I am, and then sometimes they don't, but then they realize they did, and sometimes they don't know at all. And I don't really, like, talk a lot about it. I'm just like, this is what I do. And I'm not like, hey, so I painted Michelle, and I would like to paint you too.

[Torre]

That's not a bad opening. So you photograph me, and then what happens?

[Amy Sherald]

And then I proceed to figure out the background color based off of what you have on. And then I paint the canvas, the color of the background, and then I draw the figure onto the color with charcoal so that I can work and rework it, like. Cause charcoal wipes off. And then I start the painting. But by that time, I figured out the palette of the whole piece. So the colors may change, but the pose never does change. Because once I capture that pose through the viewfinder, then that's. That's it. And that could take me up to an hour, depending on, like, how comfortable they are. And because the paintings are so simple, and I don't paint people like, hey, like, hands in the air or whatever. So it's like, I really have to focus on building, like, a psychological tension with these little movements and little things, like your. You know, your hand might be in a fist. And I might like move your finger up like a quarter of a centimeter, like just to create mid motion kind of movement, even though the rest of the body is still. But I think those things are highly legible when you look at the work.

[Torre]

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[Amy Sherald]

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[Torre]

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[Amy Sherald]

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[Torre]

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[Amy Sherald]

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[Torre]

Hardest part of the body or the face to do?

[Amy Sherald]

The face is easy.

[Torre]

I feel like you put a lot of effort into noses.

[Amy Sherald]

Yeah, like pretty much every other painting, I make one of the eyes higher than the other by accident and then I have to go back and fix it. Cause I just like get into it and then I forget to look at what I'm doing.

[Torre]

That would be very precautive.

[Amy Sherald]

And then I'm like, you know, then I have to ask everybody in the studio, like, come look at this. Do you see anything wrong? Because then I'm too lazy to really change it.

[Torre]

But you said like a millimeter Off.

[Amy Sherald]

Yeah. It's like a millimeter like that. But sometimes it's just enough. Because if their head isn't tilted. If their head's tilted, I can kind of get away with it. Because everybody's face isn't symmetrical.

[Torre]

Right.

[Amy Sherald]

But I tend to paint them symmetrically because if somebody's nostril. One nostril is bigger than the other, and I paint it that way, then people think that I drew it wrong.

[Torre]

Right.

[Amy Sherald]

So I try to. So everybody gets a little plastic surgery or. What do you. What would you call that? Paintbrush surgery? Yeah. I don't know, but. Yeah. So those are the.

[Torre]

The eye. A lot of other people have said to me, the eye is a particular challenge because it's such a focal point.

[Amy Sherald]

Yeah.

[Torre]

Because it's such a. It's so expressive.

[Amy Sherald]

Yeah.

[Torre]

Right. I mean, is that true for you, or you're like. No, the eye's easy.

[Amy Sherald]

I think they're easy. I think they're hard when I'm not painting the right person, though, because if I can feel their spirit in it, then I can get that to come out of the eyes. You know, there's some paintings, like, if you go to the National Portrait Gallery, there's some paintings in there that are dead. Like, you look at them and they're just. It's just color on a canvas. Like, that's it. You know, the eyes are dead. And it's not even that. It's not painted well. It just doesn't have any living energy in it. And I don't know how some paintings end up with that living energy and how some paintings don't. But you can see the difference.

[Torre]

You don't know how.

[Amy Sherald]

I don't know how. I just know I see it.

[Torre]

You know, you see it, but you don't know how, you know.

[Amy Sherald]

And it doesn't have to be realistically painted, because Alice Neel's paintings, for example, have that living energy in them.

[Torre]

Is what we see in the Mona Lisa. Like, perhaps the most famous example that.

[Amy Sherald]

I saw, the Mona Lisa, I was not impressed.

[Torre]

I was not impressed either. But I wonder if it's because it's already, like, culturally dead to us, because we've seen it a million times when we first encountered it. But the reason why it's shown all over the world is because at some point it had this energy that people were like, oh, my God, the eyes are alive.

[Amy Sherald]

I'll have to go back and look at it again and not do it.

[Torre]

What's a famous painting that people may, you know, just so People may have a visual reference that you say this is alive.

[Amy Sherald]

I don't know. Like, I'm thinking about this painting that I saw when I was. It's between LL Cool J and Michelle Obama at the National Portrait Gallery.

[Torre]

The Kehende LL Cool J painting. Another one that's between.

[Amy Sherald]

Yeah, it's between them. It's a scientist. Some like a bug scientist or something like that. And I went there. I went down there for the reception for the National Portrait Gallery competition. And I was speaking to a friend of mine who had work in it, and I was telling her, your portraits are. They live and they breathe. And I gave her that picture as an example. But it doesn't even have to be humans. It can be a landscape too.

[Torre]

Sure.

[Amy Sherald]

There's just something that certain artists are able to push into it that other artists aren't able to do. And maybe I can find you. Maybe you can post it on the website. I can maybe find two images where you could kind of see that. Cause it's really hard to describe.

[Torre]

Okay.

[Amy Sherald]

Yeah.

[Torre]

It's interesting that you, you know it. I mean, as expert as you are, you know it, but you don't know how.

[Amy Sherald]

I don't know how it works. I just know it's like when I studied with ah, Nerjam in Norway. He showed it to us and my mind was blown. Cause it was just like two landscapes. And I'm like, how is this even possible? But this one has an eternal feeling to it, like it's alive. And this one is just paint it. And it's nice and it's great. And they're both painted at the same level of expertise. Yeah. But this one has something that this one doesn't.

[Torre]

So the last time we talked, you said that your waiting list is longer than your life.

[Amy Sherald]

Yeah. Like, you will not since like 2016.

[Torre]

You will not fulfill your waiting list.

[Amy Sherald]

No.

[Torre]

Because it goes, what, it's what, 60, 70 years long?

[Amy Sherald]

Yeah.

[Torre]

How many do you know?

[Amy Sherald]

But some of those people, you know, within the gallery world, like, there's some people that will only buy work for. From an emerging artist. Right. So they're only going to buy work from like $6,000 to like $50,000. And once it reaches beyond that price point, they don't. They're either they're priced out or they don't want it, you know, so that list has. It's changed and.

[Torre]

But how many do you do a year?

[Amy Sherald]

13, if they're all regular size. But with these larger paintings, probably 10.

[Torre]

You can do 10 a year.

[Amy Sherald]

Yeah.

[Torre]

And your waiting list is what, a hundred or something?

[Amy Sherald]

Probably, yeah.

[Torre]

200?

[Amy Sherald]

Yeah.

[Torre]

So does that mean that you can't really change your style?

[Amy Sherald]

Well, honestly, I don't feel like I could anyway. I mean, I feel like once you become known for something, that's what people want, you know? So Coca Cola can't change the flavor of Coke. It's like Coke, people would be pissed. They don't want it, you know, And.

[Torre]

I'm not saying you should.

[Amy Sherald]

I can develop my work.

[Torre]

Not saying you should. I love your style. But there's.

[Amy Sherald]

But I thought about that before I even got into it, because, I mean.

[Torre]

I think about, like, I don't know, somebody like, let's say Damien Hurst, right. Like, there's different eras of Hearst, he does different things. That's not.

[Amy Sherald]

He's multidisciplinary though. Like, you expect that from him. Cause he's so highly conceptual. You don't expect the same thing from him.

[Torre]

Okay, so let's say Warhol, right, There's different. He does different things at different times.

[Amy Sherald]

Yeah.

[Torre]

And that is. I wonder if because of the way your business has succeeded, you're like, I can't change because there's already a thousand people who want this.

[Amy Sherald]

You can change if it makes sense for the work, you know, like, you have to grow as a person, so you can't be controlled by the market. But what I do is what I do. So if I do change, it's gonna be along, along the lines of what I do and it's gonna make sense, you know, like, it made sense for Kehinde to take those paintings and make them into three dimensional works, you know, so those kinds of changes make sense. And like, for me, it made sense for me to go from smaller paintings to larger paintings, but I didn't wanna go to large paintings just for the sake of it. Like, it had to help me tell my story in a more powerful way, you know, it had to make sense for me to make large paintings. And so at this point, like, when I think about my future, I don't really. I don't know how the work is going to evolve, but I know I have to continue to push myself in order to stay interested in what I'm doing. And I know that I could. I say this now, but I know that I could say, for example, never be an abstract painter. It's just too hard for me to leave things undone. So I think the figure is like, that's what I do. And so you see me go from speckled backgrounds to flat color backgrounds to, you know, beach scenes. And so that's what's changing right now, is that I'm, you know, with these larger works, I'm able to create these different narratives and these different kinds of scenes and people and. But I don't. I don't. I don't think I will change so much so that you won't be able to look at it and not know that I did it.

[Torre]

I mean, you are.

[Amy Sherald]

But who knows?

[Torre]

You were already a noted portraitist before you met the First Lady. But it's interesting to me that you say you couldn't be an abstractionist, because at least to me, your color choices are so interesting that even if there was no figure and it was just Amy making a color statement, I would be like, this is amazing.

[Amy Sherald]

Yeah.

[Torre]

You know what I mean? And the portrait choices are equally amazing.

[Amy Sherald]

I think it's how I see it, though, because I see work, and I'm like, I could never let that sit. You have to know when something is finished.

[Torre]

How do you know when it's finished?

[Amy Sherald]

For me, it's like. Because it's just done. Like, I can't. You know, Like, I've tightened up all the lines. I've done everything but with, like. With a Rothko or, like, something like that, you know, you have to be able to leave things undone, and you have to see beauty in something that's almost incomplete. Like, there's a science to abstraction that I don't have the DNA for, because I would overwork it, if that makes sense.

[Torre]

Yeah.

[Amy Sherald]

You know, there's definitely a finish line to cross with the figure. But with anything else, I can. I can spot a beautiful abstract painting a mile away because I look for symmetry in everything. And I feel like if you're a good painter, like, it's. It's kind of there, even if it's just in your color choices and building a foreground, middle ground, and a background. But I don't think I could leave it on. Like, I have natural hair, and it's. You. You can't. And I try to perfect it. Right? So, like, that would be me as an abstract painter. Like, I wake up in the morning, my Afro is smushed to one side of my head, and I spend 45 minutes to an hour trying to make it look like organized chaos. And it's like, you can't make your hair look. I mean, like, it's just. It is what it is. Like, it's kinky hair, you know? So that would be me. And, like, an abstract Painting each one.

[Torre]

Takes about a month.

[Amy Sherald]

Yeah, the larger paintings took a few months. They were taxing physically. It was a lot of standing on ladders for long hours and it was a lot.

[Torre]

What's the schedule? Are you afternoon painter?

[Amy Sherald]

Try to get to the studio by nine and if we're not close to a deadline, then I like to be out of there by 6:30.

[Torre]

Oh, so it's like normal working hours.

[Amy Sherald]

I want to be home. I want to go home and eat dinner and watch. This is usually, you know, I wanted to.

[Torre]

What else do you watch that you love?

[Amy Sherald]

That show specifically? And the Good Place I just came. I know it's been on for a while, but, like, I just. I just found it. I do a lot of documentaries and casual on Hulu. I think it's on CBS or something. But that show, Casual, Last man on Earth, Jane the Virgin. Jane the Virgin, Yeah. And that Moore's Chestnut police show is pretty good too. I wasn't expecting to like it as much as I did.

[Torre]

So part of the beauty of having an hour plus for this show is that, you know, I'm like, don't tell me the short story. Like, don't yada yada anything. Tell me the long story. So just for posterity, so we can have this recorded down, you know, hopefully 50, 100 years later. Tell me the whole story of the Michelle Obama Commission and like, story. Yeah.

[Amy Sherald]

Well, I was born in 1973. No, I'm kidding. I. So I won. So the way that I see it is, like, my life has been a process of things falling into place since I was born, right. And this was just another one of those things. So, you know, every artist comes to a point in their career where they need the next step to happen. Like, they're ready for it, but they don't know how it's going to happen. And you're just like standing there at the precipice and you're like, about to fall and into this eternal pit of, like, nothingness. And then the next thing pops up and it happens. So for me, that was winning the National Portrait Gallery Competition. And that was something that was completely unexpected. I went down there to receive that award. I had to borrow $150 to get down there. I had, like, negative money in my account. I hadn't paid my rent in like, four months, but I was at a residency, so they kind of let me get away with it. And I was doing the math on, like, well, if I only get like, honorable mention, that's $1,000. So I'm screwed. I'm gonna have to be an Uber driver. If I get the $7,000 award, then I'm like, I can pay my rent back, but then I don't have enough money to get ready for the show that I have coming up. So I was, like, doing all the math of, like, what I needed in order to make it through the next six months, and I ended up winning. So, like, I needed every single penny of that $25,000 I won. So that happened. I'm like, okay, this is great. And because of that, that award was publicized nationally and internationally. So side story, they started commissioning portraits for the President and the First Lady. The National Portrait Gallery started commissioning portraits with Bill and Hillary Clinton. So towards the end of the administration, they put together a portfolio of artists, and they send them over to the White House, to the White House curator. And Michelle and Barack get to go through all of them, and they shortlist five of them. So I don't know who the other artists were. They just didn't share it. So I was asking, but I didn't know who it was. So you are called to the White House. You make an appointment. You go to the White House. You get interviewed in the Oval Office. So, like, they're waiting for you. I was like, both of them. I'm always late. I was, like, late for that appointment, too.

[Torre]

Oh, my God.

[Amy Sherald]

I was, like, five minutes late.

[Torre]

So they.

[Amy Sherald]

Oh, okay. Yeah. So I'm like, yeah. In my mind, I'm like, they think I have no respect, but I'm like, literally, I can't be on time for anything. So I walk in. The White House has the ugliest fluorescent light everywhere. I mean, you know, I'm a colored person, so I'm looking. I'm like, this is atrocious. But when you walk into the Oval Office, it's backlit from, like, behind the crown molding, because it's, like, made for tv, you know? So the transition of the light made my brain do something weird. So for a second. And maybe it's because Barack was walking towards me, and I was just like, it's really a shock to see somebody in person when you've been seeing him on TV for so long. Yeah, yeah, it's weird. Cause you're like, ugh. Like, this is. You know, it just did something to my brain. So I'm just sitting there looking at him like, wow. Like, you're tall, and your ears look just like they do. And the character, like, he looks exactly. You know what I mean? Like, yeah, he's so cute. So I'm like, amy, say something, Say something. And he walks up to me, he's like, hello, nice to meet you. I'm like, nice to meet you too. And I was just nervous. Was it good?

[Torre]

Barack?

[Amy Sherald]

Yeah, I was just nervous. So, of course, it just so happened that we all had on the same color. So my friend's mom had taken me shopping to, like, get the perfect, like, sheath dress. And I had on kitten heels for the first time, but they were like leopard print blue bottoms or something like that. So I had on this, like, sheath dress that was like a taupe brownie color. He had on that beige kind of suit that everybody tweeted about when he wore it.

[Torre]

Oh, the tan top?

[Amy Sherald]

Yeah, it was like, tan suit. It was a little bit darker, though, so I think it was a different one. And she had on, like, a brown dress. And he's like, oh, looks like you got the memo. And I'm like, memo? What, did I forget something? You know, because you're not. You're like, not present. So anyway, we sat down, we had a conversation. That was the first time I met Thelma golden, too. So that was exciting.

[Torre]

Amazing curator.

[Amy Sherald]

Yeah. And so we just talked for 30 minutes.

[Torre]

Just about the two of you and Thelma.

[Amy Sherald]

Yeah. Michelle Brock, Thelma, the White House curator. I think his name is Mr. Allman, I can't remember. And another woman. What you talk about life. Like, what else I did outside of painting. Working in Baltimore City jail, community stuff. What my work meant to me, how I, you know, what the things that I've been thinking about when it came to her portrait. And then he was like, you know, how would you paint me? And I was like, to be honest, I never thought about it. And she was like, no, this is for me, honey. Like, you know, so.

[Torre]

Because you were up for both, or rather either, I think so.

[Amy Sherald]

I know that they had picked artists that could paint that painted either men really well, which I'm assuming one of them was Kehinde, obviously, and then some artists that painted men and women. So I do men and women. So I could have painted either one of them, but I think she was really interested. And I went there with the assumption of that it was gonna be me and her. So. So, yeah, I don't remember what I talked about at all. Like, I just know it was that moment.

[Torre]

What were some of the thoughts that you had for the painting you might do about her?

[Amy Sherald]

Well, the first thing I did when I found out, when I was just approached with the idea, was that Just look at all the pictures that she had on the Internet, like, so many of them. And I wanted to. I knew that I wanted to do something that felt more private. Because that's the beautiful thing about painting and portraiture, is that you can offer a more intimate part of somebody in a way that's different from photography. So I knew just that. But I didn't want to go in there with too many kind of preconceived notions or ideas, because I wanted to meet her first and just feel her energy and then kind of take it from there and like, let it happen organically. So once I found out, that was, like, July 2016, and once I found out in September, then I really started to, like, pull different looks that I liked offline. And I made a folder, and I sent some of them to her stylist, Meredith couple. And we started to go back and forth about, you know, what I wanted. So it's like, color and pattern were really important. And so she sent me 11 dresses, and I picked out four. And then we decided that we didn't want to do anything formal. And so we narrowed it down to two. And one of them was the Millie dress, and the other one was this. It wasn't the one I wanted, actually. It was like a floral print, but it wasn't the floral print that I had seen in the first image that she sent me. Cause they were all things that were on the Runway that season. And I can't remember the designer for that one. Last night, I was thinking about it, too. Cause I was wondering if it was Thom Browne. But it was really animated. But it was her. The first four years. The first four years, it was the kind of J. Crew skirts with belts and cardigans. And at that time, you know, when I. When I think about my work personally, like, it all kind of has that kind of neatness feel to it. But when I saw the Millie dress, I was immediately drawn to it because of the patterns on it and because they read, you know, they read European art, but they also read to me, like, the Gee Spin Quilters was the first thing that I thought of when I saw that. And so, for me, that was a way to tie her into black history without it being, like, you know, super, like, I guess, didactic or whatever. But I really wanted the floral dress first. But then, like, the more we got into the process of it, the more I realized that that Millie dress was, like, the perfect dress. And so she showed up to be photographed, and I decided to only photograph her in that one And I just nixed the other one.

[Torre]

Go back for a moment to. Because we went a little fast through having the conversation to them saying, okay, it's you. Yeah, I mean, did they call you?

[Amy Sherald]

The Kim Sayit from the National Portrait Gallery called me and said, what are you. Can you sit? Are you sitting down? And I was like, standing there with paintbrushes in my hand because I was working because I had a deadline. And they told me, and for some reason I tend to be very under reactive in situations that I should be overreactive. So I was like, okay, that's cool, that's cool. I'm glad she chose me. And I sat down for a second and I picked my dog up and I was like, your mom's gonna be famous. You know, like, I had a moment, but I never really had one of those, like, eee. Like people jump up and down screaming. I never had one of those. But I did have a few moments in the car, like that year, because it had to stay a secret for. It was supposed to stay a secret up until the unveiling, but somebody leaked it. But it had to stay a secret for a year and a half. I had moments in the. You know how you're like, just living your life and all of a sudden you feel everything that you've accomplished in your life in like 5 second span, and it makes you tear up, but then it goes away as quickly as it came. Yeah, it's kind of like that, you know, where I allow. I don't want to say I allowed myself to feel it, but like, it would leave. It would become present in my emotional space. I could be sitting at a red light or something and it would just. I would feel the gratefulness of, like, having a heart beating in my body that belongs to another woman. Having this opportunity and recognizing that this, like, I'm living my dreams, you know? And so all those, like, moments of gratitude, like, I would have those moments of gratitude about being chosen. And what that meant for me was like, just the opportunity to give back, you know, which is, like, really important to me, so just being able to pay it forward. But I never was like, oh my God, you know, I was just like, I'm just not that person.

[Torre]

So when you look at science fiction, they talk a lot about the year 2020. A lot of people predicted that by now we would be in the future, teleporting to work or living on Mars. Where's my jetpack? I don't have a jetpack. And none of us do. Maybe Elon Musk does. But a lot of predictions about the future were wrong. Usually predictions about the future are wrong. They say, if you want to make God laugh, make a plan. So we never really know what's going to happen in the future. So that's why you need to get life insurance, right? That's where policygenius can help. Policygenius makes finding the right life insurance a breeze. In minutes, you can compare quotes from the top insurers and find the best price. You can save $1,500 or more a year using PolicyGenius to compare life insurance policies. And once you apply, they handle all the paperwork and the red tape. They make it easy. And they can also help you find the right home or auto insurance or disability insurance, whatever you need. And when you have the right insurance, you can sleep well at night knowing if the future happens, you'll be covered, you'll be taken care of. So if your science fiction dreams for 2020 still haven't become scientific fact, don't get discouraged. Get life insurance. It takes care of you and your family. God forbid something happens. And it just takes just a few minutes to find the best price and [e-mail] policy genius. Because we always get the future wrong, so we gotta get life insurance, right? If you love Torre's show and you miss the days of me talking about politics on msnbc, and really, who doesn't? Then check out my other podcast, Democracy Ish, where I sit with Danielle Moody Mills and argue and strategize about the 2020 race from a black and progressive perspective.

[Amy Sherald]

The way in which fucking media failed this past weekend. Some of the most reputable outlets to some of the trashiest ones, they all fucking failed.

[Torre]

You can find Democracy Ish wherever podcasts are streamed. All right, back to Torre show. I think when something nice happens to me, you have that moment of excitement, but you. And I think I can also be under reactive in the same way. But then you also have that moment of responsibility.

[Amy Sherald]

That's where I'm also like, that kicks.

[Torre]

In, holy crap, I gotta do this and I gotta be good at this. And oh, wow, this is a lot.

[Amy Sherald]

I was like, oh, shit. Black tw Twitter. And what if black Twitter hates it?

[Torre]

Were you really thinking about black Twitter?

[Amy Sherald]

Black Twitter's mean, man. Black Twitter don't like you.

[Torre]

You need to like, move to another country. I mean, suddenly this. I mean, I've done, you know, a thousand paintings and this is the one everyone will see and will judge me on. And like, yeah, so you feel the pressure.

[Amy Sherald]

You Do. Because everybody loves her. Literally, the whole world loves her. So it's like trying to make the perfect painting of Jesus should be black, should it be white, should it be tan?

[Torre]

You know, she's bigger than Jesus.

[Amy Sherald]

She's bigger than Jesus. Exactly.

[Torre]

So you gave her. Let me say it this way. The day the paintings were unveiled.

[Amy Sherald]

Yeah.

[Torre]

My mom called. She did not know you. She's. She loves the art world. She did not know you. And she said, mm, I don't like the color of Michelle Obama's skin. And I was like, mom, that's what Amy Sheryl does. And she's like, mm, I don't like it.

[Amy Sherald]

And I'm like, a lot of people did. A lot of. I would say a lot of black people didn't. Right.

[Torre]

So take me back to. Now I'm conceiving this, and I'm gonna go with my skin choice.

[Amy Sherald]

That's why she chose me. I didn't force that on her.

[Torre]

She knew that you were gonna give her that gray black.

[Amy Sherald]

Absolutely. That's why I.

[Torre]

Did you talk about that choice specifically, or you were like.

[Amy Sherald]

Yeah, it wasn't even a real conversation. It was like, I like your work, and I want you to be the one to paint me. And I'm like, well, this is how I paint. She's like, that's what we want. You know, like, that's why the painting is hanging in the National Portrait Gallery. I mean, I think that's why my work is what it is. I mean, it's like, I do. I do Amy Sherrill. And I. And if. If she didn't want me to paint her that way, then I would have been like, I'm really sorry, but I can't take this job.

[Torre]

Okay. Did you think about what is Black Twitter, black America, black, whatever, going to say? They're like, you know, I forgot Realistic.

[Amy Sherald]

I forgot in that moment, I didn't think they didn't like it. I didn't think it was going to be about their gray skin. I thought it would be about, like, you know, the dress or something. You know, like anything. But I forget there's people out there that don't know anything about the art world. And, you know, I should have remembered because I had this one experience where I was doing this mural on a public housing building in Baltimore, and I had to meet with the, you know, like, the building community leaders. Like, there were some elders in the building, and they wanted to have some say, so what was on their building? And when they saw my paintings, one of them was A painting of this older black gentleman. He had on a seersucker suit with a bow tie, and it had a rabbit and a fedora. And it reminded this. He must have been like 67 or 70. He was offended by it because it made him think of minstrels. And so it's like we have different ways of seeing ourselves based on how we're seen in the world. And his granddaughter looked. He's like, well, my granddaughter looked at it and she thought it was beautiful, but she's also not carrying the same baggage, you know, so it's like, I thought it was gonna be like, some kind of issues like that. But I know that everybody is not familiar with conceptual art. And there's work like my friend Jefferson Penders that, you know, in the art world is fantastic. And he had a piece hanging in like a corporate lobby somewhere. And like a FedEx driver came in to make a delivery. She was offended by it. And it was like, you know, he's a black artist and this is a black person. And so, you know, I wasn't thinking about that though. I don't know why I wasn't. But I wasn't thinking about the skin part because I'm like, what's the big deal about the skin? But I got like one email, I got this woman was like, we had a first. We had our first black lady, and we couldn't even have a painting, have her painted as a black woman. But I'm like, she is painted as a black woman.

[Torre]

Yeah.

[Amy Sherald]

You know, so it's just.

[Torre]

I mean, her.

[Amy Sherald]

You just gotta be ready. I mean, because, like, what this man thought was art, what he wanted me to paint on the side of that building was like the black man holding the world in his hands and a black woman. You know what I mean? Like, that's not.

[Torre]

I mean, her skin color has meant a lot to a lot of people. Right? To see a light skinned man choose a darker woman has meant a lot to a lot of people. You didn't lighten her. But I think for some folks, like my mom were like, but that's not her color. Like, so what? She's like, I get it, but that matters to me. And I'm like, but then, you know, I think it's generational. It's art. It's so much.

[Amy Sherald]

I mean, it's subjective. It's subjective. It is.

[Torre]

When you showed it to her, are you nervous or you like, I nailed this.

[Amy Sherald]

I wasn't there. Like, they sent her an image of it, and then Dorothy Moss texted me back. And she said. Michelle said, congratulations, you did it. So I was like, I'm good. After that. I'm like, I'm good. She likes it because it wouldn't have been, you know, it wouldn't have been unveiled if she didn't like it. And just like Kehinde. Like, Kehinde finishes, I think, way before I finished mine. And so they emailed it to them. Michelle was like, it needs to be redone because it's. It doesn't show any of Kehinde's style. And they thought it was like, too conservative or something like that. So he got to do. He did a second painting of Barack because of that. So, like, if they didn't like it, it wouldn't be out there because they.

[Torre]

Didn'T think it was.

[Amy Sherald]

She didn't feel like it fully represented her. It wouldn't be out there.

[Torre]

Cause it didn't represent him enough Kehende.

[Amy Sherald]

Enough Kehinde. And I wanna say that for some reason, I'm under the impression that I might be making this up, though, but that he might have had a tie on and he wanted to do it without a tie. But don't quote me on that.

[Torre]

But how thoughtful of, like, it's not about us, it's about you. Yeah.

[Amy Sherald]

Because we don't. It's like they chose us for a reason. They chose us because there's like this break in history right now.

[Torre]

Yes.

[Amy Sherald]

And everybody needs to know this happened, you know, and these fortress have to be as special as the moment because they may not ever happen again. You know, so it's. So that was really important.

[Torre]

Also. Really important to your life. You have another woman's heart.

[Amy Sherald]

I do.

[Torre]

What's her name?

[Amy Sherald]

Kristen Lynn Smith.

[Torre]

How did she die?

[Amy Sherald]

Of a heroin overdose.

[Torre]

And you needed a heart for 10 years.

[Amy Sherald]

Yeah. The way. Yeah. I was diagnosed with heart failure when I was 30, so my heart function was 18%. But with transplantation, you can't be placed on a list until you're literally about to die and you have to be hospitalized. So you live with a weak heart for as long as you possibly can, and then if you're lucky, you get one. So I just say, I was really lucky. I got one. There's people. I had a friend who just died waiting on her second heart transplant. She got one when she was 16 and it was time for her to get another one. She was like 34, 35, and she didn't make it. So it's really, you know, you're not living with that while you're waiting. You're kind of, like, in this really pleasant place of denial, like, everything's gonna work out. But afterwards, I was like, wow. Like, I'm very lucky that this worked out, that I was in the state that I was in, in Maryland, that I was in the hospital that I was in, and that they hadn't. They hadn't changed the rules. They've changed the rules since then. They make it even harder for people to get organs now. Like, your organs. Your other organs have to be breaking down. Like, organ. You have to be an organ failure. And then they put you in the hospital. So then by the time you get a heart, you're, like, half dead. Which for me, I think the reason why I'm doing so well is because I was like, I was at 5% heart function, but my other organs were fine. Somehow my body compensated. And so you get the heart, and then it's easier to recover when you're not, like, falling apart, frail, and, like, you know, so.

[Torre]

But yeah, so when you're at 18 or 10 or 5%.

[Amy Sherald]

Yeah.

[Torre]

I mean, you can't just breathe. Go have a normal day.

[Amy Sherald]

No, I did. I mean, I was walking around because I was an athlete my whole life. At 18%, I was still, like, doing light exercises.

[Torre]

What was your sport?

[Amy Sherald]

Track, long distance running, weightlifting, like, so.

[Torre]

Like, marathons or, like, crossing.

[Amy Sherald]

I was training for triathlons.

[Torre]

Triathlons.

[Amy Sherald]

Then I had to stop. So, like, the day before I got diagnosed, I had run, like, 15 miles, but I didn't know anything was wrong. So, you know, basketball players or athletes, they just, like, drop dead. The heart stops. I remember that because nobody knows they have heart failure. It would. I would have been one of those people. But I pushed to get an examination before I was gonna do this, like, big race. And then I found out randomly that I had heart failure, but I didn't have any symptoms.

[Torre]

How many triathlons have you done?

[Amy Sherald]

I haven't done any. I didn't get a chance to.

[Torre]

You were training for the first one?

[Amy Sherald]

Yeah, yeah, I've been training for two years.

[Torre]

You could swim?

[Amy Sherald]

Yeah, I learned how to swim. I could swim as a. You learn how to swim as a kid? But, like, I learned how to, like, swim swim, where you're like, you know, you're turning your head like two sides, right? Yeah. You're really comfortable in the water.

[Torre]

No, I still can't.

[Amy Sherald]

My mom can't either. But you got to learn.

[Torre]

I know, and I'm telling my kids, you got to learn. They're like. But you don't know how to swim. And I'm like, shut up. Get in the water.

[Amy Sherald]

Yeah, I was just in Barbados and my. The driver that we had there was telling us that they just throw the kids in the water. I learned how to swim because they just pushed me out the boat.

[Torre]

So now you're at 100%.

[Amy Sherald]

Yeah, 70%. Like, nobody's heart beats at 100%.

[Torre]

Okay.

[Amy Sherald]

Yeah, that's what I learned, too.

[Torre]

So will you need another one? If you live to a certain age, hopefully not.

[Amy Sherald]

They don't really have. They know that. I think it's like, it may last, at minimum, 20 years. That's if you don't get any rejection. Like, I could walk out of here tomorrow and my body could be like, hell, no, we don't want this in us anymore. And then I would end up in the hospital and I could need another one tomorrow. Or it just could last the way it has been. Knock on wood that, you know, I may need one when I'm 65. I don't know. You just never know.

[Torre]

But you have a very Zen attitude about this. I mean, this is the loosest you've been.

[Amy Sherald]

I'm good with my life. I'm good with my life. Like, if I die tomorrow, I'm still good with my life. Like, the only reason I don't want to leave is because I gotta be here to take care of my niece and my dog, you know? And I'm in love now for the first time.

[Torre]

Right.

[Amy Sherald]

So that's amazing.

[Torre]

Found love later in life.

[Amy Sherald]

Yeah.

[Torre]

And now you're all up in it.

[Amy Sherald]

It's great. Later love is great. It's like, no bullshit.

[Torre]

You said you were catching up for lost time in terms of, like, I want to spend all my time with him because later.

[Amy Sherald]

And then I was like, okay with not having kids, you know, because I was, like, 40 and single. So I'm like, it's not going to happen. And I was fine with that. And then you meet your person and you're like, damn it, I want to have a fucking baby with you now. And so. But then you're like, 46 and you have, like, two ovary, you know, like, no eggs. So then the creative process starts, which is obviously complicated for me because I've had a transplant, so I can't. I can carry a child, but it's, like, high risk. So we're trying to figure out, like, adoption or, like, egg donor, which is weird. That's. I thought I was okay with it until a couple weeks ago. I went Online just to, like, look. You know, you can, like, partially register to the website and they send you. They like. It's like match.com. it's like. There's like a list of women and they're, you know, like, their education level, their height, their temperament and stuff like that. And, like, nobody's good enough to be me. You know what I mean? I'm like, you're not tall enough. You're not smart enough. I don't like your nose. Like, you know, because I gotta look at this kid and it's just weird. I'm like, okay. I don't know where this egg donor thing's gonna work out. Cause, like, I gotta find the perfect version of myself, right? I want the person to have my hair color at least. And, like, partially, you know, partially look like me. She has to be at least five, ten. So I don't. I don't know. It got weird, like, real fast with that.

[Torre]

Real fast. Tell me about being a rapper or wanting to be a rapper.

[Amy Sherald]

I used to want to be a rapper.

[Torre]

You still want to be a rapper?

[Amy Sherald]

I don't think I do.

[Torre]

You have bars?

[Amy Sherald]

I was like a fake rapper because I want. You remember Boss?

[Torre]

Yes.

[Amy Sherald]

I wanted to be like, detroit Boss.

[Torre]

Yeah, she's dope.

[Amy Sherald]

Yeah.

[Torre]

Yeah.

[Amy Sherald]

So you remember the Highland Place Mobsters? Remember Dallas's group, the Highland Place Mobsters?

[Torre]

No.

[Amy Sherald]

They were. They were like his first band. And I used to hang out with this guy that was in the band called Chip. His name was Chip and Fletcher. And so I was like a freshman in college. Like, went to a Catholic school, listened to Ice Cube. I blame Ice Cube on the fact that I even curse now to this day because of that song. Fuck the Police.

[Torre]

Fuck the Police.

[Amy Sherald]

He's like, police. Eat a dick. Straight up. You know why I got jacked, Jess? The other night, it was like that song. And I memorized it. I was 19 years old and everything. I've had a potty mouth ever since then. But, yeah, the rap thing didn't work out. Cause my mom was like, what are you talking about guns for? You don't have one. You know? My name was the Gold Digger.

[Torre]

The Gold Digger.

[Amy Sherald]

I'm a gold digger, A bitch killer. I wouldn't hesitate to pull the trigger on a motherfucking pussy nigga and. Didn't even coming out of my mouth.

[Torre]

Give me some more.

[Amy Sherald]

I can't.

[Torre]

Yeah, you got more?

[Amy Sherald]

Well, you see, I'm dope, I'm smooth. My lyrics come fatal. I'm kind of like that bitch from the hand that rocks the cradle Because I'm rough, I'm rugged, I'm scandalous I grab my Glock when I need to go and handle it Niggas try to step to me they gets to stretcher I'm down with the basic and can't forget my nigga Fletcher Because I'm making hits like I'm making coffee Never hesitate to say, back the fuck up off me. Back the fuck up off coffee, Stupid.

[Torre]

Wow. I'm making hits like I'm making coffee Back the fuck off. That's what's up.

[Amy Sherald]

That was the 18s.

[Torre]

That's what's up.

[Amy Sherald]

That was stupid.

[Torre]

And mom was like. Mom was like, what? No. Yeah.

[Amy Sherald]

No, no, no. I couldn't have done it anyway.

[Torre]

Cause you wanted to be a painter from early.

[Amy Sherald]

I did, yeah.

[Torre]

From when?

[Amy Sherald]

As long as I can remember.

[Torre]

Really?

[Amy Sherald]

Yeah.

[Torre]

This was always the dream.

[Amy Sherald]

It was always something that was inside of me. It was weird. It's like. I don't know what else I would have been like. It was either that or I would have been like Mashama Bailey. I would have been a chef. You know, those two things are only things that really resonated with me, was like, cooking and painting. But those weren't things that black parents born in the 1930s could, like, imagine their children doing.

[Torre]

Cooking and painting. Yeah.

[Amy Sherald]

It's like my mom was like, you want to do what? Like, what does that even mean? Like, you want to be an artist? And so, you know, 84, she still doesn't quite. She doesn't know my world. You know what I mean? So if I said, like, yeah, I. That Whitney bought one of my paintings, she'd be like, Whitney Houston. Like, she doesn't. She doesn't get it. You know, she doesn't understand that people pay a lot of money for paintings and that it's like a cultural legacy. And, you know, she just. She's just relieved that I will be financially stable. That's all she ever really cared about.

[Torre]

Yeah.

[Amy Sherald]

Is that. You know.

[Torre]

So how do you feel about the overall art business structure in terms of X collector buys your painting off the wall from Hauser and Wirth. What percentage of that do you get?

[Amy Sherald]

Industry cut is 50. 50.

[Torre]

Oh, wow.

[Amy Sherald]

Yeah. I think unless you're like, Jeff Koons, I think, because his work sells for, like, a jillion dollars. I feel like at that point, you can be like, it's gonna be 70.

[Torre]

30, or, you know, so you. You give half to your gallery. Is that worth it?

[Amy Sherald]

Mm. Yeah. When you're with the right gallery. Yeah, because they do all the work. Yeah, they're working for it. If you're like, if you're like for.

[Torre]

It, like half, like, like you're working for it.

[Amy Sherald]

Yeah. Well, they're the ones paying, you know, hundreds of thousands of dollars for like a booth at Art Basel, you know what I mean? Like, they have access to those collectors, like the, the high level collectors. And I guess you could kind of run, you could probably sell out of your studio. But I also feel like that, that you would hit a ceiling at some point. Like you kind of need, in order for your market value to increase to, you know, the hundreds of thousand thousands of millions, you kind of need that gallery brand and validation.

[Torre]

What, what does it cost to get Amy Sherrill? Now?

[Amy Sherald]

I can't say that.

[Torre]

We cannot say that. Okay. But. Okay, we can figure it out. But then if that collector sells it to somebody else.

[Amy Sherald]

Yeah, you get nada, nada.

[Torre]

But it raises the value of the next work you're going to do.

[Amy Sherald]

Well, scarcity creates value. And the reason why paintings can be sold for so much is because there's only one. But If I produced 100 paintings a year, they would be less expensive, you.

[Torre]

Know, so there's an art business choice to making 10 a year.

[Amy Sherald]

No, that's just. I'm a slow painter. Yeah, but it, but, but it works, it works, it works for me because I do, I want my production level to just be what it would be if I was doing it all myself.

[Torre]

I mean, you don't, I mean, in terms of the art world, you could hire an assistant to paint the background and then you come in and do the face.

[Amy Sherald]

Yeah, Like I have people paint my backgrounds. Like that's, you know, they can just sew a canvas and paint a background color and you know, it's, it's impossible for me to make 13 paintings a year by myself because it's only 12 months in a year. Right. So I need assistance to help me with the basic stuff, the stuff at the bottom. Or if, if there's a sweater that needs stuff filled in, then I need them to fill it in first so that I can come back and paint it. You know, like, that's, that kind of stuff just makes sense because it makes your life more efficient. And that way, as a 46 year old woman, I'm not in the studio 12 hours a day because I was like killing myself and it's just, it's, it gets to be too much and then you start to hate what you're doing. And I hated what I was doing. I love what I was doing. But I was like working seven days a week, 12 hours a day. I was like losing weight and it was, you know, I was like, I would end up in the hospital for four days with the flu and hadn't been around anybody with the flu. You know what I mean? Your body just starts to break down. So it's good to have an assistant there for a number of reasons. One, because it speeds up the process, because they can do the primary things that need to happen first. Two, because after a while, working in your studio gets really lonely. You're in there by yourself all that time. And for me, it's just like me and podcasts. And then conversations become really awkward because, like, you're like, did you hear, you know, did you hear that Terray podcast yesterday? I was like, in nervous, like, so all your references are just like strange blips. And then three, I think I enjoy making decisions. I like groupthink. You know, I think no man is a genius or woman is a genius on their own. And I came this far by myself, but I enjoy like talking over ideas with stuff or being like, what do you think about this? Like, how does that. Even if I know the answer, I like to get feedback from other people. And so, you know, I have. And I need to have a fabrication manager. She does all my ordering. And then I have Kelly, who's been my assistant for the past three years. And she's the. She's like my right hand person. And so she really helps me. I can focus on the more important things because I know that the background colors are gonna get done and these basic things are gonna get done so that when I come to it, I can just get to the nitty gritty of it.

[Torre]

So does it bother you if a collector sells an Amy Sherrill for a multiple of whatever they bought it for?

[Amy Sherald]

No. I mean, it happened if you don't get anything. It happened at auction last year. Piece go to auction for the first time last year, and that collector had purchased it early on in 2015 for less than $10,000, and it sold at auction for over $300,000. So, yeah, I didn't get any of that, you know, but you kind of know that's going to happen. And for me, it worked out well because people think that you want the work to sell for a million dollars at auction. But if your work, for example, is $100,000 and it sells for $500,000 at auction, it's $400,000 over your market value, then you can be in trouble because you have to try to catch up to that. And your work may not be able to sustain itself at that price. You may not have the collector base, you know, so it's all kinds of ins and outs to this that, you know, that, you know, unless you're a collector, you don't. You don't know about, but, you know, it is what it is. You know, like, I have a great gallery. They're fantastic. And I think the split, you know, it is what it is. It's like, that's what you grew up knowing. Like, you're going to give away 50% of your work. But when you have. When you're with the right gallery, you're making that much money because they're. They are who they are. So it's like, take your 50, because I could be selling for 15,000 and now I'm not, you know, so it's. You're making more than you ever would have by yourself. So what's your.

[Torre]

Let's talk about artistic advice for younger portraitists. What would you tell them?

[Amy Sherald]

Just figurative painters?

[Torre]

Yeah. I mean, people who are like. See Amy Sherrill as a sort of North Star. Oh, my God. Like, artistically. What. What. What do you want them to know? What do you want to tell them?

[Amy Sherald]

When. When artists come to me for things, I just say, you just have to keep working. Like, you need to keep working. This will not happen unless you continue to work. And I don't offer a lot of specific advice because I know for me, you're gonna grow if you keep working. The things that need to happen in your work are gonna happen if you keep working. So the key is to keep working and set up your life so that you can keep working. And that's all that I like to say. And I used to get frustrated when I would come to older artists for advice and they would tell me the same thing. But I get it now. It's like, you can't tell me how to make work that's gonna make me famous. You can't tell me, like, you can't show a person that, like, either they're gonna have it or they're not. But the best advice I've ever gotten was that I need to keep working and not. Not quit when I got frustrated, not quit when being poor wasn't cute, not let things get in the way. Like, for me, like, no relationships, no children. Like, I was just, like, hyper focused on what I had to do. And, like, that was it.

[Torre]

It's amazing that you were able to maintain the focus on your dream. When people are not buying the work, the personal life is not going anywhere. You're like, the bank account is in the red. What in that moment, and it wasn't a moment. What in that period of your life led you to say, just keep going?

[Amy Sherald]

You just know, like, there's something inside of me that just. That I just knew, right? So I'm not, like. I'm not a religious person.

[Torre]

You couldn't do anything else that.

[Amy Sherald]

I couldn't do anything else that there was something inside of me that told me that this was my destiny. And I don't. You know, like I said, I'm not a religious person. But I've had these moments in my life where you hear that weird voice. And for me, it's always like, a man with a deep voice. I'm not sure why, but you hear that voice and you're like. You just know to keep pushing, you know? So, like, when I also. When I talk to kids, like, my partner Kevin, makes fun of me because I had the. Micah had asked me to have some kids come to my studio one day. And, like, so 40 of them piled in there, and he just happened to be there. And I always say this. I'm like, so there's 40 of you guys in here? And I said, one of you guys might make it. The rest of you guys won't. And he was like, wow. And he was like. He was like. That made me feel so uncomfortable. Like you were killing dreams. And I was like, no. But there was that one kid in that crowd that was like, that shit ain't gonna be me. You know what I mean? It's like. And everyone else that felt defeated, they were gonna be defeated in five years anyway. If my words defeated them, then they were never gonna make it in the first place.

[Torre]

You say you will make it and the rest of you won't. Right? It's just a blanket. One of you will make it. So the one who really has the dream that won't die thinks you're right. Maybe five of them thought. Or maybe 40 of them thought, I will be the one. Yeah, right.

[Amy Sherald]

Yeah. But that's the way. I mean, that's the way that it is. It's like, you have to have that willpower. You cannot be weak. You cannot be faint of heart. Like, you have to push through, and you have to be smart. And it's not some magical moment where somebody finds you on the street. It's like there's a Strategy to this. And you pay attention to art history. You pay attention to what work is out there now, and you look for what. What art history needs. And I think, like, that's. That's what I know I did. It's like I was looking around, trying to figure out what I wanted to make as an artist, and I couldn't figure out what that was. The work that I made in grad school sucked. It was just, like, bad. And so I knew I had to figure out what I was gonna make. And it took me two years to figure it out. But I had an epiphany one day that at that point in 2009, there were. I hadn't seen any paintings of black people just being black. And I was like, that's what I'm supposed to be doing. That's the voice I'm gonna be in this conversation of all these different artists. This is what I'm gonna add to it, you know, and it was kind of around. When did you write your book?

[Torre]

Post Black 20 came out, 2012.

[Amy Sherald]

And so it was kind of. Yeah, it wasn't around. So, like, what was I doing in 2012? I was getting a hard transplant in 2012. But I think for me, reading your book was also an affirmation for me that I was kind of moving in the right direction. You know, as many conversations were being had around, like, the terminology of post black, I was like, there's. That's how complicated black is, is that there can be a post. Like, there's no post Chinese or anything like that, but that's how complicated it is. It's like, it's so crazy that that word can even exist. You know, that term can even exist post black. But there's something to it. You know what I mean? There's something to it because black is something that is technically. It's a construction, you know, so, yeah, we're trying to deconstruct here with. Without losing who we are, if that makes sense.

[Torre]

I mean, so many people have just not read the book and taken it. Like I was saying, post racial, which is.

[Amy Sherald]

Yeah, no, it's absolutely no such thing as that.

[Torre]

Yeah, yeah. I felt like there is a construction that was forced upon us by certain people, perhaps the older generation, perhaps certain members of our generation. And there is a large group of us who are saying, no, I want to perform or embody blackness differently and do it my way. And I'm not going to go for the conventions and the strictures and the traditional ways that you did it. I want to do it with more, whatever it is. And I think a lot of people heard what I was saying and I think a lot of people misunderstood it as well. And like, you know, you live with that.

[Amy Sherald]

Yeah, well, I thought it was genius. So I was like, this is. Because that's, I'm like, this is where it's at. Like, this is how we. You, you can't, you can't evolve as a person if you're constantly in a reactionary space. You can't be present inside of yourself. And we need to be present inside of ourselves in order to really think our way through all of these. Like our historical presence in this day and time. I mean, it's just so. Everything it felt, it felt really complicated. But for me that was the way to simplify was to just be like, you know, let's just start with the basics of who we are and then bring in the rest.

[Torre]

What has having money afforded you?

[Amy Sherald]

A self esteem really? You feel different when you have money. People are lying if they say they don't. Cause I feel like, I feel like I'm fine no matter what now. You know what I mean? Like, even if my boyfriend broke up with me, I'd be like, I'm fine cause I got money, you know, it's like you can make yourself like fine. I'll just like go on vacation a lot. I won't be sad. I'll go to Barbados and sit on the beach because I got money, you know. So it makes you feel. I feel like. I just feel safer. I feel better in life. I do feel a responsibility as a black person, you know, I feel like if I get money then like along this journey, I gotta figure out how I can make this, how I can make this work for my community as well. I feel a little bit irresponsible to have money, to be honest. Cause like you still don't know how to, you know, it's like I've met with like financial advisors or whatever and they're like telling me like what we were talking about, like financial planning and that kind of stuff. And they have this vocabulary, like I have no idea what they're talking about yet. So I'm like, man, I'm 46. Like I feel so stupid. Like I should know this already. But it's like I never had any money to know it already. So it's like you're just trying to figure it out. But I mean, I'm excited to have money. I'm excited I can pay back my school loans. Like the real stuff is I'm excited. I can pay back my school loans. I am excited that I don't. If I see something now, I can buy it, and I don't have to stress out about it. You know what I mean? Like, five years ago, I bought a pair of Stuart weitzman boots for 700 on a credit card, and I literally didn't sleep for 30 days. But, like, I wanted to do something nice for myself because I was like, I'm busting my ass. I'm not making any money yet. And, like, I want these boots. And so I got them, but now I can just, like, get them and not stress about it. You know, I can give money to my mom. I can. You know, I took her out of the country for the first time for her birthday. She's 84.

[Torre]

That was amazing. You. You detailed it on Instagram. It was amazing to see.

[Amy Sherald]

And it's like, so those are the gifts. Like, that's. That's the only reason why I've actually wanted money, like, really wanted it was because the times that my family could not fend for themselves, and my father having died when I was 28, and then my brother dying when he was 36, and whether it be because I'm the tallest person in the family, it was like. Or the strongest is my sister, my mom, myself, and my niece. So now I'm the sole provider for my family. And it stressed me out that I was, like, pursuing this career that allowed me to have no financial flexibility when I needed to, because I was waiting tables. So I. I could, like, pick up a shift to, like, you know, send money home if I needed to or whatever. But you don't. You can't help anybody but yourself. And that always bothered me. And so for me, it's like, just. It's a huge relief to be like, look, mom, you're going to be fine now. Like, if you need help with your insurance, you need help with your bills, like, I got you, and you can relax. And that's the biggest blessing. Like, that's. That's it. Like, just being able to help people.

[Torre]

You sound like a rapper. I got my mom.

[Amy Sherald]

I got my mom. But then everybody got their hands out, too, though. So, like, that's. That's.

[Torre]

That's.

[Amy Sherald]

That's weird.

[Torre]

That's hard.

[Amy Sherald]

That's weird.

[Torre]

Yeah. How do you say now?

[Amy Sherald]

They've. People have all asked for less than $1,000, so I haven't said no. But. But I'm trying to figure out. I'm trying to figure out how to.

[Torre]

Handle that you don't say no. Can I get 900?

[Amy Sherald]

I said no once. I did say no once.

[Torre]

I have this theory that deep down, everybody, or almost everybody is either scared or angry or sad or some combination of those three. But if we get to, like, the bottom of your emotional well, you're not like, yay, happy. Joy, Joy. But you're, like, either scared or angry or sad. Does that fit for you?

[Amy Sherald]

Yeah. So, like, okay, maybe it's scared now, maybe it's scared now. I'm scared every time I come to New York now. Except, like, I got, like. I feel like for the next 10 years I gotta be careful of my life because terrorists are gonna come get me or something like that. Like, Somani's daughter's gonna. I don't know. But those are things that I'm scared of. Like, I have very practical fears of. Like, I don't ride on the subway at 9:00 in the morning, 5:00 at night. Like, I live my life to try to avoid crowds and explosives. I don't. You know, I'm scared of.

[Torre]

Really? You're scared of terrorists?

[Amy Sherald]

I'm scared of random acts of violence. Yes. Yeah. I don't wanna. I don't wanna die that way. Like, there's ways I'm okay dying and there's ways I'm not okay dying. Like, that's not one of them. You know what I mean?

[Torre]

Yes.

[Amy Sherald]

I think about those things. I'm always looking for an exit. Like, if I go into a restaurant, I'm looking around and I'm like, okay, if somebody comes in here shooting and there's a mass shooter, which way am I gonna run? Or should I just go under the table? You know what I mean? Like, I'm always preparing myself for that kind of stuff now. So maybe it is scared. I don't know.

[Torre]

I always ask everyone toward the end, what is your superpower? What is the thing that has helped propel you to the success that you have had?

[Amy Sherald]

I'm a realist. Can that be a superpower?

[Torre]

Sure.

[Amy Sherald]

I think just because I'm a realist. Yeah. Like, my sister calls me the Dalai Lama. Because any situation I come into, if there's hostility, I'm able to mediate it so that everybody's okay. I can make everybody okay. Like, I know how to make people okay. Maybe that's the superpower. It's just like, I can make it. Situation's okay. You arguing with your wife, I can make it okay. Your dog needs a leg. I can make it. Okay. Like whatever it is, but I think just because I'm a realist, I guess.

[Torre]

Thanks so much to Amy for an awesome interview. And thanks to you for listening to Ratio gives you fuel to power your dreams because you can use your dreams like a rocket ship to blast you into a life you never imagined. You can make your dreams a reality, and this show can help. Join [e-mail] torreyshow for exclusive episodes and find me on Twitter ore and on Instagram orayshow. Please leave a review on itunes and tell your friends about the show. Torre show is written by me, Torre, produced by Jackie Garrafano. Our editor is Ryan Woodhull. Our photographers are Chuck Marcus and Shanta Covington, and our booker is Claudia Jaune. And we're distributed by DCP Entertainment. And we will be back next Wednesday with another amazing guest and on Friday, because the man can't shut us down.