By Illustration Age Staff
Published: February 12, 2021
Main Facts
Every December, the unveiling of TIME magazine’s Person of the Year issue captivates the global media landscape, sparking intense speculation, political debate, and cultural analysis. Yet, long before the chosen individual—or individuals—graces the cover, a high-stakes, highly secretive artistic process unfolds behind closed doors.
For the historic 2020 Person of the Year issue, which honored then President-elect Joe Biden and Vice President-elect Kamala Harris, TIME’s editorial staff enlisted a roster of elite artists and photographers to render potential candidates. True to the publication’s tradition of operational secrecy, none of the commissioned artists were told which figures would ultimately be selected. Among those tapped was Chicago-based master illustrator and caricaturist Jason Seiler, marking a monumental milestone in his career: his second TIME Person of the Year cover.
In an exclusive, in-depth interview with Illustration Age’s Sam Gallant, Seiler pulls back the curtain on the clandestine world of high-profile magazine illustration. From the pulse-pounding pressure of rendering future leaders under strict non-disclosure agreements to his unexpected passions—such as his love for drumming—Seiler offers a rare glimpse into the mind of a world-class visual artist working at the intersection of fine art, journalism, and politics.
Chronology
The journey from a blank digital canvas to a globally distributed magazine cover is fraught with tight deadlines, sudden revisions, and strict security protocols.
Phase 1: The Commission and the Guessing Game (Late Autumn)
The process begins weeks before the public announcement. TIME’s art directors reach out to a select group of trusted illustrators, assigning them various potential candidates for the Person of the Year title. In 2020, because the race and cultural climate were exceptionally fluid, artists were kept in the dark.
- "You never really know who is going to get it," Seiler explained during his conversation with Sam Gallant.
- Artists are given reference materials, rough briefs, and tight turnaround windows. They must pour hours of detailed labor into portraits without any guarantee that their specific artwork will ever see the light of day. If another candidate is chosen at the final editorial board meeting, the alternative artwork is archived, sometimes to be published later inside the magazine or kept entirely private.
Phase 2: Execution and Iteration
Once assigned, Seiler dives into his hyper-expressive yet deeply respectful style of caricature and portraiture. Working out of his Chicago studio, he balances structural anatomical accuracy with exaggerated emotional resonance. For high-stakes political figures like Joe Biden and Kamala Harris, the margin for error is razor-thin. The artwork must capture not only their physical likeness but also the gravity of a historic political transition during a turbulent year marked by a global pandemic and intense social reckoning.
Phase 3: The Unveiling and Public Release (December 2020)
When TIME officially revealed the joint selection of Joe Biden and Kamala Harris, Seiler’s striking illustration hit newsstands, digital platforms, and mailboxes worldwide. The release marked the culmination of weeks of secretive labor and instantly cemented itself in the visual history of American politics.
Phase 4: Reflection and Deep-Dive Discussion (February 2021)
Months after the frenzy of the launch, Seiler sat down for a comprehensive video interview with Illustration Age (published on February 12, 2021). The discussion provided art enthusiasts, aspiring illustrators, and political junkies with a forensic breakdown of how a modern masterpiece of magazine cover art is conceived and executed.
Supporting Data
To understand the magnitude of Jason Seiler’s achievement, it is essential to examine the legacy of TIME’s Person of the Year franchise and the unique demands placed on its cover artists.
- The Franchise Legacy: Established in 1927 (originally as "Man of the Year"), TIME’s annual designation is not an endorsement, a popularity contest, or a Nobel-style honor. Instead, it is awarded to the person, group, or concept that "had the most influence on the news and our lives, for better or worse."
- The Shift to Illustration: While photographic covers are common, TIME frequently turns to world-renowned illustrators when a deeper, more interpretive, and psychological representation of a subject is required. Portraiture allows artists to synthesize complex narratives into a single frame.
- Jason Seiler’s Pedigree: Seiler is no stranger to high-profile editorial commissions. Based in Chicago, his distinct artistic style—characterized by bold textures, profound depth, and uncanny likenesses—has graced the covers of numerous publications, including The New York Times, Rolling Stone, The New Yorker, and MAD Magazine. His prior TIME Person of the Year cover established his reputation as a trusted visual historian capable of handling the most scrutinized faces on earth.
- The Medium: Modern digital painting tools allow artists like Seiler to make rapid iterations while maintaining traditional painterly brushstrokes. This technical agility is vital when art directors request last-minute adjustments to lighting, expression, or composition under unforgiving print deadlines.
Official Responses
The intersection of art and politics invariably draws widespread commentary from media critics, art historians, and the creators themselves.
Jason Seiler on the Psychological Weight of Portraiture
Speaking with Sam Gallant, Seiler emphasized that capturing a political leader goes far beyond mere technical replication. It requires empathy and psychological insight.
- "When you are drawing someone who is constantly in the public eye, people feel like they know every line of their face," Seiler noted. “As an illustrator, your job isn’t just to copy a photograph. It’s to capture a living, breathing presence—their energy, the weight of their responsibilities, and the moment in time they represent.”
Reflecting on the secrecy surrounding the TIME commissions, Seiler highlighted the adrenaline-fueled nature of the assignment:
- "You work in this little bubble of intense focus. You know the stakes are high, you know millions of people are going to see it, but you have to block all of that out and just solve the visual problem in front of you."
Media and Art Community Reception
Following the publication of the interview and the rollout of the cover, the broader illustration community lauded Seiler’s ability to balance journalistic integrity with artistic flair. Peers praised his handling of light and shadow, noting how the portrait of Biden and Harris projected a sense of solemn optimism suited to the historic moment.
Art critics pointed out that Seiler’s background in caricature gives him an uncanny ability to emphasize character traits that photographs often flatten. By subtly accentuating specific facial landmarks, Seiler creates portraits that feel more authentic to the viewer than a standard high-definition photograph.
Implications
The collaboration between TIME magazine and artists like Jason Seiler carries profound implications for the fields of editorial illustration, journalism, and visual communication in the 21st century.
1. The Enduring Power of Illustration in a Digital Age
In an era dominated by instantaneous digital photography, high-end illustration offers something unique: human interpretation. Algorithms and cameras capture raw data, but an illustrator filters that data through human consciousness, personal style, and emotional intelligence. Seiler’s work proves that hand-crafted, nuanced portraiture remains indispensable for major journalistic milestones. It elevates a news magazine from a daily record of events to a timeless cultural artifact.
2. The Evolution of Political Iconography
Covers like the 2020 Person of the Year issue shape how future generations will remember specific historical epochs. When historians look back at the turbulent transition of power in late 2020 and early 2021, they will not only reference policy papers and news broadcasts; they will look at visual markers like Seiler’s cover. The imagery helps codify the public mood—balancing anxiety over national division with cautious hope for the future.
3. Inspiration for the Next Generation of Artists
By pulling back the curtain on his creative process through platforms like Illustration Age, Seiler demystifies the path of a professional illustrator. For emerging artists, understanding that even master illustrators face tight constraints, intense pressure, and the reality of discarded drafts provides invaluable perspective. It reinforces the reality that commercial art is a rigorous blend of disciplined craftsmanship, problem-solving, and adaptability.
As the media landscape continues to evolve, the partnership between premier journalistic institutions and visionary artists like Jason Seiler ensures that the stories defining our world will continue to be told with depth, beauty, and uncompromising human perspective.