By Sam Gallant
Published: February 12, 2021
Main Facts
The unveiling of TIME magazine’s annual Person of the Year issue is a hallmark event in American media, steeped in high-stakes anticipation, artistic intrigue, and tightly guarded corporate secrecy. For the landmark issue featuring then-President-elect Joe Biden and Vice President-elect Kamala Harris, the prestigious publication tapped acclaimed Chicago-based illustrator and caricaturist Jason Seiler to bring the historic political figures to life.
The assignment marked Seiler’s second time creating a cover for TIME’s coveted Person of the Year franchise. However, like many high-profile editorial commissions, the process was shrouded in mystery. To prevent leaks, TIME routinely hires multiple artists and photographers each year to depict a wide range of potential candidates, keeping creators in the dark about who will ultimately make the final cut until the magazine officially hits newsstands and digital subscriber inboxes.
In an exclusive interview with Illustration Age, Sam Gallant sat down with Seiler to peel back the curtain on this high-pressure assignment. The conversation explored the intricate mechanics of illustrating world leaders, the intense secrecy demanded by top-tier editorial outlets, and the surprising parallels between Seiler’s meticulous artistic process and his lifelong passion for drumming.
Chronology of an Assignment: From Secrecy to Public Unveiling
The journey toward a TIME magazine cover is rarely a straight line. It is a grueling, highly compressed timeline defined by strict confidentiality agreements and rapid-fire creative pivots.
Phase One: The Speculative Brief
Months before the public ever catches a glimpse of the Person of the Year, TIME’s editorial and art direction teams begin quietly laying the groundwork. Artists are approached under strict Non-Disclosure Agreements (NDAs). They are given vague parameters and asked to develop portraits of various front-runners. During this phase, Seiler—alongside a roster of other elite visual artists—was tasked with rendering likenesses of multiple potential candidates without knowing whether his work would anchor the definitive historical record of the year.
Phase Two: The Pivot and Execution
Once the editorial board finalizes the selection, the chosen artist is notified—often with an aggressively tight turnaround time. For Seiler, capturing the likeness of Joe Biden and Kamala Harris required striking a delicate balance between editorial commentary, realistic portraiture, and his signature illustrative exaggeration. Working out of his Chicago studio, Seiler balanced reference imagery, lighting studies, and structural block-outs to construct a vibrant, emotionally resonant double-portrait that met the rigorous demands of TIME’s art directors.
Phase Three: The Worldwide Launch and Reflection
The process culminates on launch day, when the magazine drops globally. For the artist, the moment of public release transitions into a wave of press engagements and deep reflections on the project. The interview between Sam Gallant and Jason Seiler captured this exact post-launch window, offering a rare window into the psychological weight of capturing the faces that dominated the global stage during a tumultuous historical epoch.
Supporting Data & The Mechanics of Editorial Illustration
To understand the magnitude of Seiler’s achievement, one must examine the rigorous standards of TIME’s art department and the demanding technical ecosystem of modern high-end illustration.

- Editorial Competition: TIME commissions dozens of artists annually for its end-of-year packages, making selection for the primary cover an elite distinction within the commercial art world.
- The Secrecy Protocol: The publication’s multi-artist vetting process ensures that even if preliminary sketches are leaked or commissioned art circulates internally, the final cover choice remains entirely insulated from public speculation until publication day.
- Medium and Technique: Seiler is renowned for his hybrid approach, blending traditional drawing foundations with advanced digital painting tools. This allows him to manipulate textures, lighting, and facial structures with microscopic precision—a vital skill when rendering high-stakes political figures whose faces are scrutinized daily by millions.
- Career Milestone: While Seiler has built an illustrious career creating covers for publications like Rolling Stone, The New York Times, The Village Voice, and MAD Magazine, securing a second TIME Person of the Year cover places him in a rare tier of contemporary American illustrators.
Official Responses and Perspectives
While corporate statements from TIME’s editors typically emphasize the journalistic gravity of the Person of the Year franchise, the personal perspective of the creator offers a far more intimate look at the assignment.
Speaking with Illustration Age, Seiler discussed the surreal nature of seeing his artwork magnified across global news channels, billboards, and digital screens. Rather than viewing politics through a partisan lens, Seiler approaches his subjects through the objective, structural eye of a caricaturist. He focuses on bone structure, expression, micro-expressions, and how lighting accentuates character.
Furthermore, Seiler touched upon an unexpected theme during his conversation with Gallant: the rhythm of creativity. Drawing parallels between his fine art workflow and his love for drumming, Seiler noted that both disciplines require an innate sense of timing, muscle memory, improvisation, and an unwavering commitment to practice. Just as a drummer maintains a steady beat under pressure, an editorial illustrator must maintain technical discipline while racing against unforgiving publishing deadlines.
Implications for the Art and Media Industries
The collaboration between Jason Seiler and TIME magazine underscores several vital trends in contemporary media and commercial illustration:
1. The Enduring Power of Illustration in an Age of Photography
In an era dominated by high-resolution digital photography and AI-generated imagery, high-end editorial illustration continues to hold a distinct, irreplaceable value. Unlike a standard photograph, a commissioned illustration offers a layer of interpretive commentary and psychological depth that a camera lens simply cannot capture. Seiler’s work on the Person of the Year cover proves that hand-crafted, stylized portraiture remains a powerful tool for visual journalism.
2. The Evolution of the Editorial Artist as a Brand
For modern creators like Seiler, high-profile assignments serve as powerful catalysts for career longevity. By pulling back the curtain on his process—through interviews, video features, and direct engagement with communities like Illustration Age—Seiler demystifies the commercial art industry, inspiring a new generation of illustrators and digital painters.
3. The Psychological Weight of Visualizing History
Portraits of political figures are never neutral; they shape public perception and become permanent artifacts of history. When an illustrator captures a President-elect and Vice President-elect at a critical juncture in a nation’s history, their work becomes part of the historical archive. Seiler’s ability to navigate this responsibility without losing his distinct artistic voice highlights the vital intersection where fine art meets contemporary news media.
To watch the full video interview between Sam Gallant and Jason Seiler, check out the embedded media feature above, and visit Jason Seiler’s official portfolio at jasonseiler.com.

