By Illustration Age Staff
February 12, 2021
Main Facts
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 high-stakes drama, the coveted assignment is much more than a magazine cover—it is a cultural artifact that freezes a chaotic year in time. Behind the scenes, the editorial staff at the prestigious periodical engages in a rigorous, highly confidential process, commissioning various artists and photographers from around the globe to depict a wide range of potential candidates.
Because of the secrecy surrounding the final editorial decisions, participating artists are often kept in the dark. Hired creators produce multiple portraits of various contenders without ever knowing which one will ultimately grace the newsstands and digital subscriber feeds.
For the historic 2020 Person of the Year issue—which ultimately honored then-President-elect Joe Biden and Vice President-elect Kamala Harris—TIME tapped renowned Chicago-based illustrator Jason Seiler. Marked as his second time creating a TIME Person of the Year cover, Seiler’s distinctive, highly expressive style brought the momentous political transition to life.
Recently, Sam Gallant of Illustration Age sat down with Seiler for an in-depth, exclusive discussion. The wide-ranging interview explores the intense pressure of painting world leaders under absolute secrecy, the surprising parallels between visual art and drumming, and what it truly takes to succeed at the pinnacle of commercial illustration.
Chronology: The Making of a TIME Cover
The journey from a blank digital canvas to a globally recognized magazine cover is fraught with tight deadlines, sudden revisions, and strict confidentiality agreements. While the public sees only the polished final product, the timeline of a TIME Person of the Year commission is an exercise in endurance and adaptability.
Phase 1: The Call to Action (Late Autumn)
Months before the public announcement, TIME’s art directors quietly reach out to a select roster of top-tier artists and photographers. For Jason Seiler, receiving this call is familiar territory, yet it never loses its thrill—or its terror. The initial brief is intentionally broad. To protect the integrity of the editorial process and prevent leaks, artists are asked to produce speculative portraits of multiple frontrunners.
Phase 2: Speculation and Creation in Isolation
Working under strict Non-Disclosure Agreements (NDAs), Seiler must channel his creative energy into multiple directions simultaneously. During this phase, the artist relies heavily on reference materials, historical context, and quick sketches. Every stroke is executed with the understanding that the artwork might be benched if the editorial board pivots toward a different candidate at the eleventh hour.
Phase 3: The Verdict and Final Polish
The exact choice of who will be named Person of the Year is heavily guarded—often known only to a tiny circle of top editors until the magazine is physically ready to roll off the presses. For Seiler, discovering that his artwork of Joe Biden and Kamala Harris had been selected came concurrently with the rest of the world seeing it on newsstands and digital banners. Once chosen, frantic final adjustments are made to color palettes, lighting, and composition to ensure the piece reproduces powerfully across thousands of media channels.
Supporting Data: The Anatomy of a High-Stakes Commission
To understand the magnitude of Seiler’s achievement, it is vital to examine the metrics and cultural weight surrounding TIME’s Person of the Year franchise.
- Historical Significance: Established in 1927 (originally as "Man of the Year"), the franchise highlights the person, group, or concept that "most influenced the news and our lives, for better or worse."
- Global Reach: A TIME cover is distributed to millions of readers across print and digital platforms, making it one of the most visible commercial illustration assignments in the world.
- Artist Selection Roster: TIME historically alternates between premier portrait photographers (such as Platon or Annie Leibovitz) and world-class caricature and digital painters. Seiler belongs to a very elite group of illustrators trusted to handle political figures of this magnitude.
- Technical Medium: Seiler predominantly works in digital painting media (such as Adobe Photoshop and Procreate using drawing tablets), allowing for the rapid iterations required by fast-moving news cycles while maintaining rich, painterly textures that mimic traditional oil or acrylic mediums.
Official Responses and Insights from the Interview
In his conversation with Sam Gallant, Jason Seiler opened up about the realities of working at the highest levels of editorial illustration. While the video interview captures the dynamic back-and-forth between the two creatives, several core themes emerged regarding Seiler’s artistic philosophy and career trajectory.
On the Pressure of Painting Presidents
Capturing the likeness of a sitting president or vice president is intimidating enough, but doing so under the magnifying glass of a TIME cover multiplies the pressure exponentially. Seiler noted that caricature is often misunderstood as merely exaggerating features for comedic effect. In the context of serious journalism, however, exaggeration becomes a tool for psychological excavation.
"You aren’t just trying to map a face; you’re trying to capture a moment in history, a mood, and an underlying narrative," Seiler explained during the discussion. Every wrinkle, shadow, and expression is loaded with political and emotional subtext. When painting public figures who evoke deeply polarized reactions from the public, the artist must walk a fine line between biting commentary and respectful journalistic depiction.
The Unexpected Connection: Art and Drumming
Beyond his prowess with a stylus, Seiler is an avid musician, specifically a drummer. During the interview, Gallant and Seiler explored the fascinating intersection between rhythm and visual composition.
Seiler drew direct parallels between keeping time on a drum kit and balancing a complex illustration. Both disciplines require a strict sense of timing, structural foundation, and dynamic flow. Just as a drummer uses accents and pauses to drive a song forward, an illustrator uses contrast, focal points, and negative space to guide the viewer’s eye across a canvas. This rhythmic approach to image-making helps explain why Seiler’s portraits possess such palpable energy and movement.
Implications for the Future of Editorial Illustration
The collaboration between TIME and Jason Seiler highlights broader trends in the modern media landscape. As photography becomes ubiquitous—easily accessible via smartphones and AI generation tools—the value of human-crafted illustration has shifted. Commissioning a master illustrator like Seiler is a deliberate editorial choice. It injects a distinct human perspective, a psychological depth, and a narrative flair that a standard photograph simply cannot replicate.
Furthermore, the secrecy and speed required for assignments like the Person of the Year showcase the resilience of traditional creative professionals in a digital age. Illustrators must continuously adapt to shifting technological tools while maintaining a fiercely independent artistic voice.
For aspiring artists watching Seiler’s career, the interview serves as both a masterclass and a reality check. Reaching the upper echelons of the industry requires more than just technical drawing skill; it demands reliability under pressure, the humility to accept heavy art-direction edits, and the ability to find creative inspiration in high-stress, fast-paced environments.
As media formats continue to evolve, iconic collaborations like the one between TIME and Jason Seiler ensure that the rich tradition of editorial portraiture will remain a cornerstone of how society documents and remembers its defining historical moments.
To watch the full video interview between Sam Gallant and Jason Seiler, view the embedded media player above or visit Illustration Age.
