Jess Cuevas and Justin Teodoro on Madonna's 'Celebration' Tour

Before seeing Madonna at her “Celebration” World Tour, fans would see Jess Cuevas and Justin Teodoro.

Cuevas’ signature stretched imagery — in this case, a remixed shot of Madonna in her nun-inspired costume — was projected onto a massive curtain to hide the stage, while Teodoro’s whimsical illustrations were printed across official tour t-shirts. As much as the show was a celebration of Madonna’s decades-long career, it was also a celebration among creatives across multiple different mediums, from fashion to photography and more.

Below for PAPER, the two artists reflect on the life-changing opportunity that Madonna and “Celebration” provided them both.

Jess Cuevas: Congratulations on the work you’ve done in the past and also with this tour for Madonna. I wanted to ask you a bit about what your creative process is?

Justin Teodoro: Like anything, I get my inspiration and go from there. Working on the tour was a dream job-type situation. I came in with enthusiasm that spurred my creative motivation. I was working with the costume team and they shared all these images and references, and I helped put it together in an illustration that would sell the idea. My background is in fashion. I worked in fashion probably, like, 10 years ago. I was a designer before I made this leap into focusing more on my art illustration. So I had those muscles that I could take out and flex, and help sketch flats and everything. I don’t mind getting thrown all these things and it was very collaborative, which I like. The whole process is a moving train, it takes a village, so it was cool seeing how I could help get things going.

Jess: So you worked directly with the costume department before the t-shirt designs started?

Justin: I was brought on by [“Celebration” Tour Costume Designer] Eyob Yohannes. When I was working in fashion, he was styling the shows at the company I was working with, so that was my connection. And I remember when he was assembling the team, maybe in late 2022, he was looking for an illustrator to come on board. When I got the call I just said “yes,” right away. “I’ll do it, I’ll figure everything out afterwards.” [Laughs] Honestly, I didn’t really know what to expect, but it was cool doing stuff with the dancers and working with the team. Everyone was so nice and I made great friends. I’m sure you know, too, that always helps the experience.

Jess: I don’t think I could do this work without the kindness of a team. We have to choose our battles, and sometimes the jobs aren’t that and you’re just like, “Oh my god, what the fuck,” but it was so refreshing. Everyone is very, very kind.

Justin: Yeah, this was my first time doing this type of thing, like a world tour. I remember, I was sketching and watching, observing, taking in what I could. Everyone is so busy doing what they’re doing, you’ve got to take it in on your own and make it work to keep your part going. So that’s how I started and then the t-shirts came towards the end of last year, which is the cherry on top.

Jess: With those images, specifically for the t-shirts, were those what you chose to push forward or did they come to you with like, “Oh, we’d really love your spin on this?”

Justin: I had some sketches that I’ve always done. Big Madonna fan, so I would always be sketching her. Even as the tour started, I was sketching on my own. Luckily, I could get my artwork shared to the team and that’s how they chose them. So there wasn’t any direction, I think they responded to the pictures that I had, which is very cool.

Jess: That’s so beautiful. I’ve watched your art for so long and you’re so fast, it’s amazing. Do you ever feel a block? Are you ever inspired by something and then you’re like, “Oh, I really want to do this fast,” and then maybe it doesn’t come through? And if so, how do you push through that?

Justin: I, like anyone, get creative blocks. I’ve just learned sometimes you can’t force it and that’s the best thing. Walk away and take a break. I’m freelance, so I juggle different projects and that also helps me. If one thing isn’t working, step aside, come back to it.

Jess: Sometimes you gotta let that moment pass. Okay, so I love bootleg stuff and I’ve been watching where our [tour] artwork has ended up. How do you feel about your art being reinterpreted and put into different countries on different bootlegs? Is it flattering for you?

Justin: Honestly, it is. Madonna fans are a real diehard group. It’s been amazing, just seeing the responses. Especially in Mexico City, I could pick out, “There’s me and there’s Jess,” it was very cool. You always have the little business voice, but at some point you can’t stop the moving train. I always think art should be shared and art should be for everyone. And I liked the interpretation, like some things I didn’t even think about.

Jess: Totally, I was like, “This is so cool.” The art becomes something else. Now you’re interpreting it. Yeah, Mexico City and Rio were both like, “Whoa, these are sick.”

Justin: It was wild, almost like Warhol’s factory with the multitudes.

Jess: I know, the volume. It was so cool. What is your favorite Madonna video?

Justin: Obviously, “Vogue,” I love. “Ray of Light,” “Music,” “Cherish,” I love. After seeing the tour, “Live to Tell.” The song itself and how it was used in the show is amazing. It took on a new meaning for me.

Jess: With that, your favorite Madonna song?

Justin: That’s hard. I remember as a kid I had older sisters and cousins, and that’s how I really discovered music and pop culture and Madonna. So a special thing for me, for whatever reason, is “Into the Groove.”

Jess: Yeah, I was gonna say that too.

Justin: I just remember responding to it as a kid and the lyrics of dancing, but dancing by myself. How about you?

Jess: I graduated in ’95, so it was high time for her, and my aesthetic and my formative brain. So, for me, it’s “Justify My Love.” That video was it, for me, and it still kind of is. I reference that a lot with different shoots I might have or different ideas of examples with high contrast, black and white. Looks, everything, makeup, the whole thing. That video and song and all the remixes that came with that, it was also the first CD single I ever bought. I still listen to it and I’m like, “That is so fucking good.” It could drop today and still be so fresh. That really simple beat from a Public Enemy song, which Public Enemy is another one of my favorites.

Justin: I remember seeing the work you did for the tour when everything was announced, and I was blown away. How would you describe your signature style and how did you work that into the tour?

Jess: I started seeing images and thinking about how to take what’s already there and reinterpret it. I was doing that a bit with the brand I work with, Willy Chavarria. One of the first ones I did was I took a coat, called the “monster coat,” and I made it really giant. I really like the idea of using imagery that’s already there and that may be relatable, and pushing it in a different direction. But it’s still recognizable, and it’s still cool and sexy.

So with these images, I have such a memory. I used to illustrate a lot in high school and I would draw that corset image. We all, as Madonna fans, have this relationship to these images, so I wanted to make sure that I was still honoring the originality. That you could look at it and be like, “Oh my god,” but maybe I’m having a weird dream. That was my approach, and also making sure that they remained as sexy as they were back then and, ultimately, that Madonna was into it.

Justin: You kept its essence, but the elongation, the exaggeration. There’s something still kind of high fashion.

Jess: Thank you. I was always obsessed with those nine-headed figure model drawings. So taking that love and moving it to photographs, elongating the body. Also, the comment of where we are right now in a society of filters. Moving the work through that is my inspiration.

Justin: Do you have a favorite among them?

Jess: I love the “Erotica” one because that was the first one I did and that I had shown her. I did that a long time ago, so when they approached me about doing the art work it was referenced again. And I was like, “Oh my God, this is so crazy.” I can’t believe I took a chance in sending this art and now it’s the thing.

Justin: So that was the first one?

Jess: “Erotica” was one of the first ones I did referencing the ’90s for her. There was a selection of images given to me and then I would interject ones that I thought could be a cool addition. Those made the cut, as well, so that was really amazing.

Justin: Even the costume side of this tour was very collaborative. You could do what they asked, but then it was open and they encouraged you to put your own spin on something.

Jess: Totally. For both of us, we’ve created this world of imagery and we’re lucky that people can come to us for that. We have this moment in time for this tour, so why not just go for it? What’s the worst thing they can say? “No?”

Justin: It was nice to feel that respect. Like, “Do your thing and let’s see what happens.” So, obviously, your image was shown before every show started. What was that like? What was your first reaction?

Jess: I had been working with them a bit before and [Madonna’s stylist] Rita [Melssen], months and months ago, sent me that image and said, “I think you could do something cool with this.” I don’t know if it was a universe thing, but I had put it on the backburner. I didn’t even think about it for a while. When the tour was about to start, it came to me and I thought, “I should make something and I’m just gonna send it to her as a ‘thank you,’” completely separate from any tour imagery. And I did, it came to me really fast. The image was a screen grab, so it wasn’t intended to be that. So I had sent it and, you know, “Thank you, love it, moving on.” When the tour was about to start, Ricardo [Gomes] asked if they could use it for the beginning. And things move fast, next thing I know that was up. It became the most shared image of the tour out of the work that I did. I do not have words for that.

Justin: Where were you when you first saw it?

Jess: A friend of mine was going to London for the opening and sent me a photo of the curtain. I was like, “Oh my God, no way.”

Justin: You didn’t know it was going to be that scale?

Jess: Everything was moving so fast at that time because there was the pause while Madonna was getting better. With this whole thing, I did not understand the scale. I’ve never worked like that, where something goes from zero to boom. It’s a first for me, so I didn’t realize what was going to happen. And then when I was able to see it for myself in LA, I was like, “Wow, I’m so grateful.”

Justin: That’s major. It sounds like it’s full circle, how you were looking at all those iconic images and doing your twist. Now you’ve made an iconic image of Madonna, yourself. That’s a major honor and very well-deserved.

Jess: Thank you, and same to you. Another thing I wanted to say, as far as artists, I really appreciate that you and I shared each other’s work. We met through this and I think in a world that can be so competitive, I just wanted to say I’m super grateful.

Justin: Now that the tour has ended, how do you feel? Bittersweet?

Jess: I do feel bittersweet, but I also love that this project hit such a big climax and was such an amazing journey to be a part of. Watching the show from Rio and to see it all end in that way, looking beautiful and perfect. 1.6 million people, that is everything that the tour and that woman deserve.

Justin: Totally. That was such an amazing show to watch and see that’s how it ended. And yeah, I agree. It’s bittersweet, but something always ends–

Jess: And something else begins.

Photo via Getty

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