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The Violet Files

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Cassandra Grey sits down with the movie star who is currently working on working on herself.

Photography by
Cass Bird
Creative Direction by
Cassandra Grey & Vicen Akina
Makeup by
Tasha Reiko Brown
Hair by
Kim Kimble
Nails by
Betina Goldstein
Styled by
Anda + Masha
Production by
Starkman & Associates
Casting by
Jill Demling
Fashion & Beauty by

When I was dreaming up the world of VIOLET GREY, I wanted to steal a page from the magazines I worshiped, namely the celebrity cover. A good cover story, and cover image, allows one to get up close to a type of star power that is otherwise intangible and out of reach.

We set out to create our own version of the celebrity cover story: one that was singularly digital, which in 2013 required a certain amount of both naiveté and audacity. Over the years, we captured images of everyone from January Jones (in a bathtub, famously), Cindy Crawford, Eva Mendes, and Kim Kardashian (transformed by Pat McGrath into Cleopatra), to a relatively unknown-at-the-time Margot Robbie. A great cover story is entirely dependent on securing a star that is resonating within the culture, but who, at the same time, has a secret quiet vulnerability that makes us all desperate to know more. For this Cover Story in collaboration with CHANEL, we only wanted Alexandra Shipp.

Arriving on set in Los Angeles with no makeup, no hair, no nails, no wardrobe, and without Cass Bird’s in-demand eye and proprietary lighting package, Alexandra Shipp is already impossibly gorgeous, causing all of us to audibly gasp as she glides by the racks of CHANEL and the oversized man guarding millions in high jewelry, and sits down in Tasha Reiko Brown’s makeup chair as if she owns the set and has never known anything different. Wearing baggy 90s jeans and sneakers, she smiles at me through her reflection in the lighted makeup mirror and I know she is perfect for what we want to capture today: stolen moments, as seen through a voyeur’s lens. Images of a glamorous young star ascending to Hollywood’s top ranks. An ingénue whose career is about to explode.



But Alexandra Shipp isn’t exactly brand-new, fresh out the box. It’s been a decade and a half since, as a 17-year-old with her mother’s blessing, she bravely packed up and moved from Arizona to Hollywood to follow her dream. Since then, Shipp has appeared in nearly 40 films and television productions, including the Oscar-nominated Straight Outta Compton, the critically acclaimed tick, tick… BOOM!, the poignant coming-of-age coming out story Love, Simon, and most recently, the cultural phenomenon that is Barbie the movie, playing Barbie, a role that she described to me in our Wiretapped phone interview, below, as one that shined a spotlight so bright that her feet may have lifted from the ground, causing her the kind of feelings that beg to be worked through in therapy, and posing the question as to why self-worth is so often measured by what we do, rather than who we are?

Fumbling with the recording device and feeling like an imposter interviewer, I ask the tragically unoriginal question that I guess I thought a real interviewer would ask an actress: “What are you working on right now?”  

“What am I working on right now?” Alex, as I know her, replies, without taking a beat: “I’m working on myself.”




CASSANDRA GREY: Are you okay with me recording you? 


CG: When we first got on the phone, I asked you what you are working on, and you said you are working on yourself.  

AS: On a daily basis, that's what I'm really, truly doing.

CG: I am interested in the self-development work you are doing in the context of your career choice, meaning, let’s just boil it down to the perception of you, which is that you are a star, right?

AS: Yeah.

CG: You are a star. 

AS: I'll receive that. Thank you.

CG: I think that for many, becoming a celebrity seems like it comes easily to actors. 

AS: It is easy to romanticize.

CG: The late talent agent Sue Mengers once said, “Stars are rare creatures, and not everyone can be one. But there isn’t anyone on Earth—not you, not me, not the girl next door—who wouldn’t like to be a movie star holding up that gold statuette on Academy Award night.” I think a lot of people would really love to be a star, or to know what it is like to be a star. So, your audience, in many cases, is made up of people who want to be you, and your success often makes them aware of their own unrealized dreams. But fame can be the worst drug of them all. In my observation, people who have endured fame struggle with their identity and self-worth and don’t always make it. It is remarkable that at 32, with 15 years of showbiz under your belt, you are currently “working on yourself,” despite fame attempting to fuck with your perception of yourself and your value. It can be so distorted to be thrown into living up to what you're meant to be or what others want you to be. It must be debilitating, to say the least?

AS: It is. And it's funny because I love how the universe works. This is something that I've been working on in therapy, coming out of this big, beautiful Barbie experience. I've been asking myself: “What is my worth? What falls in line with what I'm doing and how that defines me?” The conclusion I've come to is that my worth is not defined by what I do, but by who I am. It is debilitating to work in a business of constant rejection. And, though, don't get me wrong, that was a choice, I don't think anyone truly understands what “I'm going to move to LA and I'm going to make it big,” really looks like, because even with success comes major, major hardship.



CG: Knowing in your bones exactly what you want to do in life is such a gift, but then you’ve got to come to terms with the fact that you have chosen to express yourself through art, and you’ve now given the world permission to analyze every part of you.

AS: One hundred percent. 

CG: Dissect you.

AS: One hundred percent.

CG: And, celebrate you, of course. Which is nice, if you're comfortable with that. But ultimately, as a star, do you have a heightened sense of responsibility because you are aware that the way you express yourself and live your life can influence other people? 

AS: One thousand percent. 

CG: Did you always imagine that you would be a star?

AS: What's kind of funny is, yes. When my mom moved out to LA a couple of years ago, I went back to Arizona to help her pack up my childhood home. We were going through all of these old boxes because, as most mothers do, she saved everything. And there was this school paper where we had to write what we wanted to be when we grew up. On my paper, it was split down the middle. I said I either want to be a famous actress or a pop star.

CG: Did you make a line in the middle? 

AS: Right directly down the middle. I said, either-fucking-or, or I'll take them both. 

CG: Famous actress or pop star, that is the question.  

AS: At the time, I was really obsessed with The Bodyguard, and with the idea that I could be both. I was a big fan of Whitney Houston growing up, and I was like, wait, Whitney Houston is a pop star, but she's also acting in this movie. I want to do that, too.

CG: And how old were you?

AS: Ten years old. And my mom was like, “yeah,” when I told her this is who I want to be. She put me in theater; she got me voice lessons. I was really lucky that I had a mom who listened and who heard me, and who was like, “Okay, my child wants to do this; I'm going to put her in a position in which she can be able to succeed in some way, shape, or form.”

CG: Inspired action.

AS: Very much. She was like, “This is what we're doing.” Never, “Oh, sweetie, that's one in a million.” By that time, she was a two-time breast cancer survivor. I think that gave her the courage to let me do what I needed to do to be happy and to be great. She always says, “You get to choose how you show up on this Earth. So, how do you want to show up?” And that would boil down to integrity, but also to, who do you want to be in this world? I just always knew that this is who I wanted to be when I grew up. I think that's common for a lot of actors. I was so determined that this was my life's purpose.



CG: When you were thinking about wanting to be an actress, a singer, or both, could you define what made it so attractive? Did you feel like it was imagining yourself being looked at, or imagining the art, and the effect that the art would have on other people? 

AS: I think the most attractive thing to me was the energy and the feeling that I got when I did those things, when I was singing, when I was putting on little shows. Art was always a form of escape for me. I really dove into that in the beginning of my career, where I just wanted to be someone else and focus on their fictitious problems more than whatever was going on in my life—which, for a while, was a little problematic because I needed to redefine “who is Alex?” But I guess the initial appeal was just the feeling I got. It was being on stage and feeling that rush of fear and anxiety and endorphins. And I still get that. People ask, “are you nervous?” You bet your ass, I'm nervous. 

CG: Do you sing now?

AS: Yeah, I still sing. I made a conscious decision to make music for myself. When I'm working on jobs, it's hard to wind down from all of the experiences. I could have a day where I'm doing a bunch of stunts and my body's tired, but I'm still buzzing. Or I could have an [acting] experience where I die, and how do I recoup and shake that off? Music has been a part of that recuperation. So, I'll get home from a job, or back to my hotel after a long day's work, and I'll sing and play my guitar and write music for hours before I go back. 

CG: So it’s kind of like journaling—expressing the authenticity and emotion of that day with your voice?

AS: Totally. And getting out whatever I have. Sometimes I'm just sitting there playing my guitar, and the next thing I know, I've written an entire song in 15 minutes, and it's about something that I didn't even realize I was dealing with. I look at the lyrics and I think about the song, and I'm just like, “Oh, girl, you weren't even looking at that.” And then I have this divine moment of being vulnerable. 

CG: Do you ever collaborate?

AS: I do. I have some friends where I feel like they hear me and get me, and we collaborate and make really great music together. It's like a therapy session; it's like a women's circle.

CG: You're not thinking about commercial viability.

AS: Exactly. I'm not even thinking, I am just being. 

CG: You have a musical journal, documentation of your spiritual connection, recorded in voice notes, somewhere on a cloud.

AS: It's so funny because I have friends who are like, “you should just release your voice notes. Do it.” It's literally just me and a guitar or me and a piano. 

CG: I know you released one song, right? 

AS: Yeah, I've released one song professionally that I wrote with a friend of mine.

CG: Before you were acting? 

AS: No, this was two or three years ago. I did a music video for it and released it on Spotify and Apple Music. I have music on SoundCloud. I did an entire album when I was 25 and was like, I'm never going to release this professionally, but I might as well release it on SoundCloud.

CG: BRB, googling SoundCloud. 

AS: People can listen to it. It's become a little obscure at this point, and it all is very personal.

CG: Do you want to be on a stage? 

AS: I go back and forth. Sometimes I want that more than anything. And other times, I don't know if it’s in the cards for me. I think it’s a part of my ego, telling me I'll never be that. 

CG: Yeah, the dark side of the ego. 

AS: Telling me people aren't going to like it. It's not going to be a hit. I'm over 30. 

CG: Or, you just got a movie, “lemme just focus on that?”

AS: Yeah. I focus on what's in front of me. And I've done that for so long. If I were offered a tour and then also offered a movie, I guess I would take the movie. Touring is a hard life. I have so many friends in music—that is not an easy life; you are moving and shaking and not sleeping.




CG: Does it feel much riskier, much scarier, than acting in a role where you're like, “I can do this. I know how to do this. I've done this before?”

AS: It really has always boiled down to the dark side of my ego telling me that I can't do it all, I can't have it all. And the fear of, is this commercial enough? Where does my worth lie? Are people going to like it? When I play someone else in a movie or a TV series, I'm like, “Oh, well, if you didn't like a character I played, then you just didn't like the character.” But if you don't like my music?  

CG: It's much more.

AS: It is so personal and indicative of who I am as a human, not a role that I'm playing.

CG: Especially the way you make music.

AS: Exactly. I don't know that my soul could take hearing, “your music sucks.” I don't know.

CG: I am guessing you could take anything. You're still so young and new; it still feels like the beginning, even though your body of work is so successful. Do you feel successful?

AS: No.

CG: Do you have an idea of what success feels like? Do you think that when you do feel it, you're going to know what it is? 

AS: I think there are levels to it. I feel successful in my personal life. I feel like I have achieved a lot as a human being, as a woman.


AS: And that's what keeps me full. That's what keeps me happy and moving and thriving. But when I look at my career, I can't help but wonder where I am. I've been in this business since I was 17, and I'm constantly questioning who I am and what I'm doing. And if I've even done anything yet. Like you said, it feels like it's just beginning. 

CG: I think Lorne Michaels said it best: “People in show business never retire.” Rumi talked about the divine discontent of an artist. And I heard somewhere that that person who lived the longest worked the day he died. If you can maintain this feeling of being brand-new, and it’s always Day One, you remain teachable and the possibilities are endless… What happens when you feel content?  Do you stop throwing punches? Are you still pushing yourself?  How boring to have a finish line, no?

AS: Yeah. Scary.

CG: It's so scary. And it seems like a hard life.

AS: Yeah.



CG: I went to this Picasso exhibit recently that was extraordinary. It was titled, “A Foreigner Called Picasso.” Gagosian did it.  What I learned was he was never really accepted anywhere. Over his life he painted 25,000 paintings! The way he painted reminds me of how you make your music, as a chronicle of your life, of your pain, of your desires, of your joy, of your heart. He seemingly knew that this was his life's work, expressing his emotion or connection to his subconscious or sexual desire, or whatever, through this art form, documenting every step of the way, as if he knew it was great and would be studied and devoured long after he was gone. His whole life seemed to be given to art. And that's great, I guess: sacrifice, and then the legacy. Do you want to be the movie star on the stage holding the statue, or do you want to be the person who lived the life you portrayed? 

AS: That’s the age-old question. I think that for any actor, it's both, right? It’s the true plight of the artist. We want to be great. We want to do great things. What I've found in the work that I've done as an actor is that I have this beautiful, finite opportunity to change someone's perspective. I've seen this work through some of the films that I've done, like Love, Simon. When your child comes out to you, when your friend comes out to you, when your lover comes out to you and says, “I'm gay,” this is what you say: You say, “I love you.” It's fucking moving. And it might seem so matter-of-fact, and, “Duh, of course, thank you for telling me that. I love you.” You would think that's a common reaction, but it's not. I've seen how art can affect society in a beautiful way. Acting is a form of activism. 

CG: Education. 

AS: Education. That was the original point of theater. When we go back to the Greeks, they were trying to educate the illiterate masses about what was happening in society. The whole point was: This is what's happening in the government. This is what's going on with Caesar, or what have you. You know what I mean?

CG: That's why the pressure of this responsibility is so big. 

AS: It definitely comes in hot, but what is my level of activism? Who am I as an activating human being? It was hard for me to figure that out. In 2020, when the world was shut down, and we were looking at all the protesting and the BLM movements that were going on in our country, I was like, “Ew, I'm an actor. Why didn't I go to school for political science?” I felt so out of touch. And I was like, “Who am I? Am I even human? Do I have a voice?” I worked on it in therapy, and my therapist said, “Well, the roles that you play, are they written for people like you, people who look like you?” And I was like, “No, in no way, shape or form.” And she was like, “Well, then that's your level of activism. You're showing a different perspective and showing up within that perspective.” And I was like, “Okay. That's a narrative I can get behind.”

CG: You are at such a young age and have experienced so many things—the distractions of addiction, heartbreak, glamour, fame. Getting through all of that and being able to wake up in the morning and know you are authentic, and that you are expressing your deepest, most meaningful emotions through art, that is success. You have the fear, but you also have faith. 

AS: I've been lucky that I've been such a consistent listener. Even when I didn't want to be right, even before I got sober, I was still listening to my own ideas of what I want to be when I grow up. And I'm still trying to achieve her. But I am also hyper-aware of how that has evolved and changed over the years. When I was 10, I wanted to be a rock star and a famous actress. In my twenties I wanted to win awards and to be on the cover of magazines. Now, I want to be someone who sets a bar of, this is how to treat people. This is how to show up. This is how to have integrity. I would like to be an example because I think that is a more conducive legacy for where I am in my life.

The real question that I have been genuinely asking myself is, what is happiness, and am I happy? When I look at what happiness is right now in my life, happiness comes from fulfillment. I'm just trying to stay present. It’s funny when people ask “what are you working on right now?” I'm working on myself, and I'm working on being present. That's what I have right now.