Lindsey Olivares, the Annie Award-winning designer behind The Mitchells vs. The Machines, brings energy and personality to everything she creates. Her bold, dynamic style shines in animation, portrait art, and beyond.
In this article, we’re excited to showcase Lindsey’s take on celebrity caricatures, turning famous faces into playful, vibrant illustrations. By emphasizing key features while keeping the heart of each subject, Lindsey offers a fresh, fun perspective on the stars we know so well.
Scroll down, are you able to recognize all of the faces? Let us know in the comments!
More info: Instagram | lindseyolivares.com | x.com
#1 Timothy Chalamet
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We reached out to Lindsey to learn more about her artistic journey, her passion for caricature art, and the creative process behind her unique character designs. When asked how she got her start as an artist, she said that making art has always been a big part of her life. “I grew up in a creative family where the arts were always celebrated. I studied animation at Ringling College of Art and Design, trained in character design during an internship at Walt Disney Animation Studios, and began my animation career as a visual development artist at DreamWorks Animation.”
#2 Billie Eilish
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#3 Rami Malek
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Lindsey shared that her caricature style developed naturally while spending a lot of time drawing from real life. “The more I trained in draftsmanship and understood drawing fundamentals, the more freedom I had to break realism and stylize.”
One of Lindsey’s early caricature influences was Craig Kellman, a character designer she worked with at DreamWorks. “Craig has an incredible sense of comedy in his work, and drawing caricatures of each other in the office gave me the confidence to be bolder with my own drawings. Later, I discovered the International Society of Caricature Artists (ISCA), where I found a network of deeply inspiring caricature artists. ISCA hosts an annual convention, ISCAcon, where hundreds of caricature artists from around the world gather for a week to draw each other. Every year I attend, I come away with a ton of inspiration from this amazing, diverse community of artists.”
#4 Reese Witherspoon
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#5 Nina Simone
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To Lindsey, caricature is less about exaggerating unusual features and more about capturing a person’s true likeness and personality. “People often misunderstand caricature as simply finding a ‘weird feature’ or ‘flaw’ and exaggerating it. This leads to the assumption that it’s harder to caricature a ‘normal’ or ‘boring’ face. I don’t like those words and don’t subscribe to the concept of beauty standards or physical flaws. Caricature, to me, is about capturing a person’s likeness and essence. When you observe people with genuine curiosity, everyone becomes interesting.
The hardest part, I find, is distilling an entire person into a single image. If I know someone well, it’s even more challenging to feel satisfied—It’s an addicting challenge to capture all that life and personality in a single image.”
#6 Elliot Page
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#7 Elvis Presley
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Drawing live caricatures usually takes about 20 minutes, while studio caricatures—which involve more detail and adjustments—can take 1 to 3 hours.
Lindsey begins every creative process with an impression. “It can be an attitude, a posture, structure, flow, shape, or proportion. My caricatures are the most successful when I capture a quick initial impression and run with it. From there it’s a game of balancing ideas, knowing how to edit, and knowing how to trick the brain. The human brain is incredible at recognizing faces, which gives a lot of freedom to push and play while maintaining recognition.”
#8 Yoko Ono
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#9 Ariana Grande
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#10 Audrey Hepburn
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#11 Nicki Minaj
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#12 Taylor Swift
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#13 The Weeknd
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#14 Diana Ross
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#15 Stephen King
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#16 Gigi Hadid
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#17 Donald Glover
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#18 Katharine Hepburn
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#19 Naomi Campbell
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#20 Lionel Messi
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#21 Idris Elba
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#22 Adam Driver
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#23 Rosario Dawson
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#24 Nelson Mandela
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#25 Albert Einstein
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