February 12, 2021
By Illustration Age Staff
Main Facts: The Secrecy, the Stakes, and the Subject
Every December, the publishing world holds its collective breath as TIME magazine prepares to unveil its annual Person of the Year issue. Steeped in tradition, intrigue, and relentless speculation, the franchise is arguably one of the most high-profile editorial assignments in modern media. Long before the public learns which individual, group, or concept has defined the global zeitgeist over the past twelve months, a tightly guarded mechanism swings into motion behind closed doors.
Editors at the prestigious periodical quietly commission a rotating roster of elite artists, portraitists, and photographers to depict a wide range of potential candidates. The goal is twofold: capture the likeness and spirit of several frontrunners while maintaining absolute operational security. In the high-stakes realm of political journalism, a leaked cover can ruin months of strategic editorial planning. Consequently, the artists themselves are kept entirely in the dark. They paint portraits of multiple contenders without ever knowing which one will ultimately grace the magazine stands and digital newsfeeds worldwide.
For the momentous Person of the Year cover honoring Joe Biden and Kamala Harris, TIME tapped Chicago-based illustrator Jason Seiler. Renowned for his biting, hyper-expressive caricature work and technical mastery, Seiler was no stranger to the magazine’s intense pressure cooker; this assignment marked his second time producing a TIME Person of the Year cover.
In a wide-ranging, exclusive interview with Sam Gallant of Illustration Age, Seiler pulled back the curtain on the secretive process of painting world leaders, balancing commercial deadlines with creative integrity, and—surprisingly—how his parallel passion for drumming influences his visual rhythm on the canvas.
Chronology: From Commission to Unveiling
Understanding the lifecycle of a TIME Person of the Year cover requires looking at a timeline defined by compressed deadlines, sudden pivots, and meticulous secrecy.
Phase 1: The Pre-Selection Phase (Late Autumn)
Weeks before the official announcement, TIME’s art directors reach out to a select group of trusted illustrators. Contracts are signed under strict non-disclosure agreements (NDAs). At this stage, artists are given a list of potential candidates under consideration by the editorial board. For Seiler, this meant preparing multiple illustrations depicting various figures who might capture the title, depending on how late-breaking global events unfolded.
Phase 2: The Blind Execution
Working from his studio in Chicago, Seiler utilized his signature digital and traditional hybrid techniques to render high-detail portraits. Because the final selection is often deliberated right up until the magazine goes to press, artists must treat every piece as if it will be the definitive public image. They work without feedback loops from the public, relying entirely on the guidance of TIME’s art directors, who act as the sole conduit to the editorial board’s shifting thoughts.
Phase 3: The Global Reveal (December)
The tension breaks the moment the magazine hits newsstands and digital subscriptions drop globally. For Seiler, the rollout brought the surreal experience of seeing his artwork beamed onto massive screens, printed on millions of physical copies, and analyzed by cable news pundits across the political spectrum.
Phase 4: Reflection and Deep-Dive Discussion (February)
Following the whirlwind of the launch, Seiler sat down with Illustration Age’s Sam Gallant on February 12, 2021. Released via an in-depth video interview, the conversation offered a rare, post-mortem look at the psychological and physical stamina required to execute historical portraiture under extreme pressure.
Supporting Data: The Anatomy of a Modern TIME Cover
To fully appreciate Jason Seiler’s contribution, it is vital to examine the metrics and cultural weight associated with TIME’s premier franchise, alongside the technical parameters of Seiler’s artistic background.
- Publication Legacy: Founded in 1923 by Briton Hadden and Henry Luce, TIME introduced the "Man of the Year" (later updated to Person of the Year) franchise in 1927, initially as a way to cover a news-sparse week by highlighting Charles Lindbergh’s historic transatlantic flight.
- Cover Artist Pedigree: Jason Seiler is part of an elite, albeit small, fraternity of illustrators who have defined the visual identity of contemporary political figures. His work has previously graced the covers of TIME, Rolling Stone, The New Yorker, The New York Times, and MAD Magazine.
- Digital Transformation: Modern covers require versatility. Seiler’s portraits must scale effectively from a tiny smartphone notification icon or social media thumbnail all the way up to a glossy, oversized print magazine and expansive digital billboards in Times Square.
- The Medium: Seiler is celebrated for bridging traditional fine art painting techniques with cutting-edge digital tools (primarily using software like Adobe Photoshop alongside drawing tablets). This hybrid approach allows him to achieve the rich texture of oil paint with the agility required for rapid-fire editorial turnaround times.
Official Responses and Industry Perspectives
The intersection of fine art, caricature, and hard-nosed political journalism always generates significant industry commentary.
When discussing his approach to drawing powerful political figures, Seiler has consistently emphasized that his goal is never mere flattery, nor is it cheap mockery. Instead, his caricatures aim for a deeper psychological truth. By exaggerating certain facial features, bone structures, and expressions, Seiler attempts to reveal the inner personality and the intense weight of the office his subjects inhabit.
Art critics and media analysts frequently praise TIME for returning to illustration during moments of profound political transition. While photography captures a split-second reality, illustration introduces an interpretive layer. It allows the magazine to comment directly on the character of an era rather than simply documenting its physical events.
During his conversation with Sam Gallant, Seiler discussed the unique collaborative dynamic between himself and TIME’s art directors. Far from being handed a rigid blueprint, illustrators are given conceptual parameters that allow them to inject their distinct artistic voice into historical documents. The dialogue highlighted how trust is built over years of meeting grueling deadlines without compromising quality or security.
Implications: The Enduring Power of Editorial Illustration
The partnership between TIME and artists like Jason Seiler carries profound implications for the fields of journalism, digital art, and political discourse.
1. The Revitalization of Editorial Illustration
In an era dominated by stock photography and algorithm-driven image curation, high-end editorial illustration stands out as a beacon of artisanal craftsmanship. The success of the Person of the Year covers proves that audiences still crave a human touch—an artist’s hand interpreting the complex emotions of a fractured nation. When an illustrator filters a monumental political moment through their unique stylistic lens, the resulting image transcends passive news consumption and becomes an enduring piece of cultural heritage.
2. The Psychology of Caricature in Politics
There is a fine line between satire and respect in political portraiture. Seiler’s work demonstrates that caricature can be used humanely and powerfully to dignify political figures. By leaning into the distinct topography of a face, artists help the public connect with leaders on a visceral level, stripping away some of the sterile polish of traditional press photography.
3. The Artist as Historian
As Seiler discussed in his interview, the act of drawing a president-elect or a historic vice president-elect is not just a commercial job; it is an entry into the historical record. Decades from now, history books will use these covers to visually define the early 2020s. For working illustrators, this elevates the medium from commercial applied art to an essential component of historical documentation.
Conclusion
Jason Seiler’s journey from his Chicago studio to the cover of TIME’s Person of the Year issue underscores the vital intersection where fine art meets global news. Through his candid discussion with Illustration Age’s Sam Gallant, Seiler illuminated the grit, secrecy, and profound creativity required to freeze history in a single frame. As long as artists continue to find fresh ways to interpret the human face amidst the chaos of world events, editorial illustration will remain an indispensable pillar of modern journalism.
