Behind the Canvas: Acclaimed Illustrator Jason Seiler on Creating TIME’s Iconic Person of the Year Cover

By Illustration Age Staff
Published: February 12, 2021

Main Facts

Every December, the unveiling of TIME magazine’s "Person of the Year" issue triggers a global wave of anticipation, political speculation, and cultural debate. Beyond the editorial choices and the exhaustive debates over who shapes the cultural and political zeitgeist, the issue carries a rich tradition of secrecy and high-stakes artistic commissioning. Months before the public ever lays eyes on the final publication, TIME’s editorial and art direction teams quietly engage a select roster of top-tier artists, portraitists, and photographers. These creators are tasked with depicting various potential candidates, operating under strict NDAs and working entirely in the dark regarding who the ultimate choice will be.

For the monumental Person of the Year cover featuring then-President-elect Joe Biden and Vice President-elect Kamala Harris, TIME tapped renowned Chicago-based illustrator Jason Seiler. Marking Seiler’s second time creating the prestigious Person of the Year cover, the assignment required capturing the likeness, gravity, and hope of a historic political transition.

In a deep-dive interview conducted by Sam Gallant of Illustration Age, Seiler pulls back the curtain on the clandestine world of high-profile magazine illustration. The conversation explores the unique pressures of drawing world leaders under wraps, the intersection of traditional painting techniques and digital workflows, and—surprisingly—how Seiler’s parallel passion for drumming informs his rhythmic, dynamic approach to visual art.

Chronology: The Anatomy of a Top-Secret Commission

The path from an empty canvas to a magazine cover sitting on newsstands worldwide is an exercise in meticulous planning, extreme confidentiality, and rapid execution. While the public sees only the finished product, the timeline for a TIME Person of the Year cover unfolds in several tightly controlled phases:

• Late Autumn (The Secret Briefing): Months prior to publication, TIME editors reach out to a small, trusted group of visual artists. Without revealing the final winner, art directors provide specific prompts and photo references for several front-running figures. Artists must conceptualize and paint multiple portraits, knowing only a fraction of their work will ever see the light of day.
• The Conceptualization Phase: For Jason Seiler, this phase involves intense research into the subjects. Beyond studying standard press photographs, Seiler analyzes mannerisms, bone structure, expressions, and public personas to ensure his signature satirical yet deeply respectful caricatured realism strikes the right chord.
• The Final Selection and Pivot: Once TIME’s editorial board locks in the Person of the Year—in this case, Joe Biden and Kamala Harris—the chosen artist is notified at the eleventh hour. If the artist was working on alternate candidates, those pieces are shelved, and the focus shifts entirely to refining and polishing the winning portrait for print and digital distribution.
• The Launch (December 2020 / February 2021): The magazine drops globally, sparking immediate media commentary. For Seiler, this marks the end of months of secrecy, allowing him to finally share his process, sketches, and experiences with the broader artistic community, culminating in his February 2021 interview with Illustration Age.

Supporting Data: The Craft and Career of Jason Seiler

To understand the magnitude of Seiler’s selection by TIME, one must examine his extensive footprint in the commercial illustration and editorial art sectors. Caricature and portraiture often occupy a tricky space in the art world, walking a fine line between humor and profound psychological insight. Seiler has mastered this balance, establishing himself as an industry titan.

• Professional Milestones: Based out of Chicago, Illinois, Seiler has built an illustrious career spanning decades. His client roster reads like a "who’s who" of global media, including TIME, Newsweek, Rolling Stone, The New York Times, The New Yorker, MAD Magazine, and various major Hollywood studios.
• The TIME Legacy: Securing one TIME Person of the Year cover is a career-defining achievement. Securing a second places Seiler in an elite class of commercial artists who have repeatedly been entrusted with defining the visual markers of modern history.
• Medium and Technique: While Seiler initially cut his teeth in traditional mediums—working extensively with oil, acrylic, and traditional drawing tools—he has seamlessly integrated digital painting software, such as Adobe Photoshop and Procreate, into his workflow. This hybrid approach allows him to capture the organic texture of classical portraiture while retaining the agility required by fast-paced editorial deadlines.
• Educational Outreach: Beyond his commercial work, Seiler is deeply committed to mentoring the next generation of artists. He frequently conducts workshops, lectures at art schools, and shares his digital and traditional painting processes online, demystifying the path of a professional illustrator.

Official Responses and Insights from the Interview

During his conversation with Sam Gallant on Illustration Age, Seiler offered rare, candid insights into the psychological and mechanical hurdles of his craft.

Discussing the inherent mystery of the assignment, Seiler emphasized the professional discipline required to invest dozens of hours into portraits that might ultimately be discarded if TIME chose a different Person of the Year. "You pour your heart and soul into capturing the essence of these individuals," Seiler noted, highlighting the adrenaline rush of receiving the final green light from the art directors.

When asked about the unique challenges of painting political figures like Joe Biden and Kamala Harris, Seiler stressed the importance of empathy over mere replication. Unlike straightforward portrait photography, illustration allows the artist to amplify certain characteristics to reveal a deeper truth about a subject’s character, resilience, or historical weight.

In a delightful detour during the interview, Seiler and Gallant also explored Seiler’s passion for drumming. Drawing a parallel between music and visual art, Seiler explained how rhythm, pacing, and timing in percussion mirror the composition, flow, and "beat" of placing brushstrokes on a digital canvas. Both disciplines, he suggested, rely heavily on muscle memory, emotional expression, and an innate sense of timing.

Implications: The Enduring Power of Editorial Illustration in a Digital Age

In an era dominated by instantaneous digital photography, artificial intelligence image generation, and endless streams of stock media, the decision by a publication as influential as TIME to invest in bespoke, human-crafted illustration carries profound implications for the creative arts industry.

1. The Human Element in Political Commentary: Photographs capture a split second, often dictated by lighting, angles, and shutter speed. Illustrations, by contrast, are accumulated thoughts. They reflect the artist’s interpretation of a person’s soul, struggles, and historical impact. By choosing Seiler, TIME reaffirmed the irreplaceable value of human perspective in political journalism.
2. Elevating Illustrators to Cultural Chroniclers: Interviews like the one featured on Illustration Age help bridge the gap between commercial art and fine art recognition. When masters like Jason Seiler discuss their process, it elevates the status of illustrators from background contractors to vital cultural chroniclers who help visually define eras of global history.
3. Inspiration for Emerging Artists: For the thousands of students and aspiring illustrators following platforms like Illustration Age, Seiler’s journey serves as a masterclass in persistence, adaptability, and versatility. The ability to pivot between traditional painting principles and modern digital tools is essential for survival in a rapidly evolving creative landscape.

As political landscapes shift and media formats continue to transform, the intersection of journalism and fine art illustration remains a powerful tool for storytelling. Through his second TIME Person of the Year cover and his candid reflections with Sam Gallant, Jason Seiler has once again cemented his legacy as one of the defining visual artists of our time.