Artist Will Cotton Reveals How He and Katy Perry Played an Elaborate Game of Candy Land

Even as New York City avant-gardists were salivating over Will Cotton’s surreal landscapes involving candy, pastries, melting ice cream and other objects of desire, he began to wonder why there were no figures in them. “And what would someone look like if they were a figure in this place?” he asked himself.

He had his answer when Katy Perry contacted him. Their collaboration produced the demure nude-on-a-cotton-candy-cloud cover of the singer’s 2010 album Teenage Dream, plus a series of other portraits, including Cupcake Katy (above, 2010), which Cotton kept to himself for three years before selling it to the collector Jim Dicke in 2013.

Dicke has promised Cupcake Katy as a gift to the National Portrait Gallery, where it will be shown this month to coincide with a concert by Perry at Washington, D.C.’s Verizon Center. It will go on display again in 2015.

Smithsonian magazine spoke with Cotton about the painting; his collaboration with Katy; and his own unique place in American portraiture. 

Your work can be viewed at the Seattle Art Museum, the Columbus Museum of Art and now, the National Portrait Gallery. How do you feel about Cupcake Katy becoming a part of the Smithsonian's collections? 

The National Portrait Gallery is a really exiting context; its focus on portraiture is unique in the art world. I’m thrilled.

I’ve heard Katy Perry is excited, too.

That’s good! I haven’t actually talked to her directly since I knew [the donation] was happening, so I’m glad to hear that. As I understand, for the National Portrait Gallery, it first and foremost matters to them who the subject matter is; I think that’s probably a nice honor for her.

What do you think it was about Perry’s public persona that caught the Gallery’s attention?

It’s a question of cultural relevance. It seems like they must consider her to be important enough as an American to be part of the collection.  

You were behind both Perry’s Teenage Dream album artwork and her video for "California Gurls," for which you served as the artistic director. Why did you paint Cupcake Katy? 

When Katy came to pose for me for the album cover, she spent a whole day in my studio. I wound up taking lots of photographs and making some sketches. And so this portrait was not made for any specific purpose at all, other than it was an image I just really wanted to paint. It was not a commission.

Working with her was really a new experience for me. Before she came along, I had no interest in painting a recognizable person. But Katy had this kind of pop culture iconography that just seemed to me to fit into the kind of things I was already interested in painting about—particularly her posing for this picture. It was a painting I’d wanted to make for a long time with the right person, and she was the right person for it.

I’ve read before that you never paint celebrities as a rule.

Yes, I don’t see that happening. You never know, but it would take someone coming along that really seemed like such a good match. That hasn’t happened recently. The thing about painting celebrity in general is that there’s this chance that they can just completely take over the picture. You might just see, "Oh, you know, there’s Justin Bieber with some stuff around him." You don’t see anything but Justin Bieber, because a painting is this whole language of symbols. You have to feel like there’s equality—that you don’t just see one thing. With recognizable people, there’s always a danger that you do.

Your portrait of Katy seems very airbrushed, like it’s straight out of a magazine photo spread. There’s an aura of impossible perfection.

Well part of that, unfortunately, is the downside of seeing artwork online. If you saw it in person, you’d see the paint—and that’s important to me. It does make me sad; I know that they look like photographs when you see them on a computer screen. There is really a lot of paint on the canvas, and they feel very “painterly” and painted.

There’s another aspect to that perfection that’s actually [intentional]. I want the picture to be about certain things. I need for there to be a symbolic resonance of the dress, and the crown, and that it’s Katy. If I started getting into some of the more quotidian aspects of human existence—like freckles, or wrinkles, or things that are less archetypical and more mundane—then it would take the portrait in a really different direction.

It’s not supposed to be realism.

No, it’s not; not that kind. In fact, it should be idealism. That’s really the idea—that it’s ideal. And that does have a relationship with perfection.

Your paintings tend to feature pin-up-girl types of models. Katy’s a natural subject for you, since her image casts her as the living embodiment of a ‘50s pin-up girl.

I could tell from my first conversations with Katy that we shared that affinity for that kind of mid-century pin-up illustration, and that’s a very specific thought and look.

What inspired this affinity for you?

It started when the first Candy Land paintings I was making didn’t have any figures. I spent a long time thinking, “Well, what’s that about? What would someone look like if they were a figure in this place?” Of course, anything’s possible.

I just started to try to find a match; a conceptual match, like a mode of feminine depiction that’s as saccharine, as over the top, as the idea of a place made of cakes and candies. And that kept bringing me back to mid-century American pin-up painting. The way ladies are presented is just so over the top. It’s so saccharine that there’s no chance of reading it as anything but archetype. And that felt important to me, just because the person in the painting had to be a symbol on equal footing with the other symbols that we’re looking at. So if you’re looking at a painting, you’re recognizing, "That’s a cupcake, that’s an ice cream cone, that’s cotton candy—those are things I know and understand and have a relationship with." I wanted the person to have that kind of cultural, or pop cultural, point of reference as well.

Speaking of cotton candy, you use very sticky (and messy!) props and costumes, including an extensive variety of sweets. How do those sugary concoctions tend to react with the hot studio lights and the long hours of painting?

That was fun—and challenging. We had a cotton candy machine running all day long so we could constantly replenish the cotton candy cloud. I had my friend Scott running the machine and literally just throwing cotton candy around Katy as she was posing.

How did Katy like that?

She was such a good sport. She seemed just fine with it. And yes, it is sticky, so she needed some hosing down at the end of the day.

But in Cupcake Katy, she’s not covered in candy—she’s fully clothed, wearing the cupcake wrapper-inspired dress designed by Cynthia Rowley that’s also featured on the album sleeves of her Teenage Dream album. Did Rowley initially make the dress especially for Katy?

Yes, she did. It was based on a design that I made on a Barbie doll with actual cupcake papers. I had this thought that it would make a great dress; something that would be a reference to court portraiture, but also clearly grounded within the kind of Candy Land environment I paint. I brought this design to Cynthia and said, "Could you make this? Could you sew something that looks like this?” She said, "We could get it pleated!” So she did. She got it done just in time for when Katy was coming over to pose.

You once painted pop figures from American corporate advertisements; now, you paint fantastical landscapes composed of sweets. When and why did you start creating what are essentially hyper-realistic pictures of a literal Candy Land?

That started around 1996. My move away from the very specific advertising icons had to do with my wanting to be more completely original within a picture. When I was painting something like the Hamburglar, Twinkie the Kid or any of these ad icons that we knew about as children, I felt like a lot of their power was due to their familiarity—and really, to somebody else’s hand. I didn’t invent them.

As I started to move more toward sweets, I understood that [this approach] was really the more complete way for me to deal with the questions of desire, association and fulfillment that I was thinking about in the work. I wanted to find a language that could be more completely my own. And remembering that I’d played the game Candy Land as a child, I thought I could make this a real place. So I put this scenario into play in my own mind in the studio. "What if this were a real place? What would things look like? And what would portraiture ultimately look like in a place like this?" That’s what led to the painting of Katy.

The Making of Katy Perry's 'Teenage Dream' Album Packaging

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In your work, you use candy to explore themes like temptation, indulgence and perfection. Since you rarely paint celebrities, what about Katy made you want to explore those particular messages with her?

That’s a great question. It’s funny, because her image has now gotten very wrapped up in the project we did together.

I’m realizing it’s hard to put my finger on and describe exactly what it was. I mean, the pictures I’d seen of her—[back then], she had more of a fruit thing going on; she had these really outrageous, wonderful costumes. I loved the way she wore them. She’s so fully transformative, and just like an actress, she’d put herself into a different role. And there was this willingness to not take herself too seriously that felt right. There was this positivity to her presence.

It’s also her music. The first time I heard it, it just struck me as the best kind of pop; pure fun, with a message that’s heartfelt, true, but not necessarily self-conscious.

It’s very earnest, in a sense.

It is earnest, but it’s not preachy either.

You’ve collaborated with Katy on a few projects by now. What’s it like to work with her?

With Katy, it was very much like how I’ve worked with anybody else—it was her knowing my work and coming into the studio with a willingness to become part of that. I found it to be so much fun. To see her around the people she works with, my first surprise was how completely in charge she is, both in a creative and administrative sense. She said, "I think this is good," "I think this is not good," and "This is how we should do it." I’ve only worked with her a tiny bit. But that was my experience; she’s very self possessed, and just incredibly charismatic. She’s very much in charge of her own career.

Are you going to team up with her again in the future?

That’d be fun. I guess I would. As I said before, there are very few people who are well-known that I feel have any potential relationship to my work—and she’s one of them. So yes, I would happily work with her again.

You painted multiple portraits of Katy, but you kept Cupcake Katy to yourself for several years before selling it. Why did you hold on to this particular painting? Was it your favorite? Does it hold special meaning for you?

I feel like there’s something about the way she’s sitting there, with the scepter and crown and her very stern look. She looks very queen-like. All of those things, along with her gaze directly at the viewer, make it a very important painting to me. 

She looks regal.

Regal. That’s the word I was looking for. She looks regal. That’s it. Most regal.

Kirstin Fawcett | READ MORE

Kirstin Fawcett reports on the collections, exhibitions, new research and other happenings around the Smithsonian Institution.