Behind the Brush: Illustrator Jason Seiler on Capturing History for TIME’s Person of the Year Cover

February 12, 2021
By Sam Gallant (Adapted via Illustration Age)

Main Facts

Every December, the publication of TIME magazine’s "Person of the Year" issue sparks a wave of global anticipation, media speculation, and high-stakes mystery. Far beyond a simple editorial assignment, creating the artwork for this landmark edition is one of the most prestigious—and secretive—commissions in the visual arts.

For the monumental issue recognizing Joe Biden and Kamala Harris, TIME enlisted acclaimed Chicago-based illustrator and caricaturist Jason Seiler. Marking the second time Seiler has been tapped to paint the magazine’s prestigious Person of the Year cover, the assignment required navigating strict confidentiality protocols, tight deadlines, and the immense artistic pressure of capturing two of the most scrutinized political figures on the planet.

In an exclusive interview with Illustration Age’s Sam Gallant, Seiler pulls back the curtain on his creative process, discussing the clandestine nature of high-profile magazine commissions, the nuances of drawing world leaders, his unexpected parallel passion for drumming, and what it truly takes to translate contemporary politics into timeless art.

Chronology: The Making of a Cover

The journey toward a TIME Person of the Year cover is rarely straightforward. It is a carefully orchestrated sequence of events designed to prevent leaks while ensuring the magazine hits newsstands and subscriber mailboxes on schedule.

Phase 1: The Speculative Phase

Months—and sometimes weeks—before the official announcement, TIME’s editorial staff commissions a diverse roster of elite artists, illustrators, and photographers. During this phase, artists are typically kept in the dark regarding who the final selection will be. Instead, they are asked to produce a wide range of potential portraits depicting various frontrunners and shortlisted candidates.

For Seiler, this meant stepping into a high-pressure sandbox where every stroke of the digital brush had to be executed with the highest level of craftsmanship, even though there was no guarantee his work would ever see the light of day.

Phase 2: The Brief and the Silence

Once the editorial board finalizes the Person of the Year—in this case, then-President-elect Joe Biden and Vice President-elect Kamala Harris—the chosen artist is formally briefed. However, strict non-disclosure agreements (NDAs) are immediately enforced. Artists are barred from sharing their progress, discussing the commission with family or peers, or posting sketches on social media.

Phase 3: Execution and Refinement

Working under intense time constraints, Seiler utilized his signature digital painting techniques to capture not just the physical likenesses of Biden and Harris, but their dynamic presence as a historic incoming executive team. Revisions happen at a rapid pace, with TIME art directors providing real-time feedback to ensure the portraits align with the publication’s distinct journalistic tone.

Phase 4: The Global Reveal

The secrecy culminates on launch day, when the magazine hits newsstands globally. For the artist, this moment marks the sudden transition from working in absolute isolation to seeing their artwork analyzed by millions of readers, political pundits, and fellow creatives worldwide.

Supporting Data: The Anatomy of a TIME Cover Commission

To understand the weight of Jason Seiler’s achievement, it is helpful to examine the scale and impact of TIME’s Person of the Year franchise:

• Historical Legacy: Established in 1927 (originally as "Man of the Year"), the franchise highlights the individual, group, or concept that wielded the most influence over the news and our lives over the preceding 12 months, for better or worse.
• Visual Storytelling: While photography frequently dominates magazine covers, TIME has a rich, decades-long tradition of employing master illustrators and painters—such as Boris Artzybasheff, Ronald Searle, and Tim O’Brien—to deliver conceptual depth that a standard photograph cannot always achieve.
• The Artist’s Pedigree: Jason Seiler is no stranger to high-profile clients. Beyond TIME, his striking, highly expressive caricatures and digital paintings have graced the pages of Rolling Stone, The New Yorker, The Atlantic, and The New York Times, alongside extensive work in the animation and film industries.
• Dual Portraits: Painting a dual-subject cover introduces unique compositional challenges. Balancing the visual weight, lighting, and psychological expressions of two distinct political figures—while maintaining harmony within a vertical magazine format—demands exceptional mastery of design and color theory.

Official Responses and Insights from the Interview

During his conversation with Sam Gallant, Jason Seiler offered profound insights into the realities of commercial illustration at the highest tier. While the full video interview captures the dynamic banter between the two creatives, several key themes emerged regarding Seiler’s artistic philosophy:

Navigating the Pressure of Political Art

When asked about the inherent stress of painting figures as polarizing and prominent as the President and Vice President, Seiler emphasized the importance of staying grounded in the fundamentals of observation. Rather than focusing on political commentary or public opinion, his primary objective as an illustrator is to capture humanity, texture, and character.

"You are looking for the story behind the face," Seiler noted in discussions surrounding his portraiture work. Capturing a likeness goes beyond mere physical mapping; it requires understanding the subtle micro-expressions, posture, and energy that define a person under pressure.

The Intersection of Art and Music

In a surprising twist, the interview also explored Seiler’s parallel passion for drumming. Far from being a mere hobby, Seiler draws a direct correlation between the rhythm of music and the visual cadence of illustration.

• Timing and Composition: Just as a drummer maintains a steady tempo and navigates dynamic shifts in a song, an illustrator must manage pacing, negative space, and visual rhythm across a canvas.
• Discipline: Both disciplines require thousands of hours of repetitive, solitary practice to achieve a level of effortless execution when it matters most.

Implications for Modern Illustration and Digital Art

The collaboration between TIME and Jason Seiler for the 2021 Person of the Year cover underscores several broader trends in the contemporary art and media landscape:

1. The Enduring Power of Illustration in a Digital Age

In an era dominated by instantaneous digital photography and AI-generated imagery, hand-crafted illustration offers a vital human element. Artists like Seiler infuse editorial commentary with empathy, wit, and psychological depth. A painted portrait allows the viewer to see the subject through the interpretive lens of another human being, creating a richer narrative connection than a standard press photo.

2. The Evolution of Digital Caricature

Seiler has long been a pioneer in bridging traditional academic painting techniques with digital mediums like Adobe Photoshop and the iPad Pro. His work proves that digital tools, when wielded by a master draftsman, can achieve the rich textures, luminous color depth, and emotional resonance historically associated with oil on canvas.

3. Raising the Profile of Illustrators

Platforms like Illustration Age play a crucial role in demystifying the commercial art industry. By spotlighting creators like Seiler, the broader creative community gains insight into the rigorous preparation, professional discipline, and artistic integrity required to succeed at the apex of magazine publishing.

Conclusion

Jason Seiler’s second TIME Person of the Year cover stands as a testament to the enduring marriage of world-class journalism and exceptional fine art. From the absolute secrecy of the early conceptual phases to the global exposure of launch day, Seiler’s work on the Biden-Harris cover cements his status as one of the preeminent illustrators of our time. Through his conversation with Sam Gallant, aspiring artists and art enthusiasts alike are granted a rare, inspiring glimpse into the mind of a master creator who continues to shape how we visualize history as it happens.