February 12, 2021
By Illustration Age Staff
Main Facts: The Secrecy, the Stakes, and the Subject
Every December, the release of TIME magazine’s "Person of the Year" issue triggers a wave of global anticipation, political speculation, and media scrutiny. Beyond the editorial debates over who best shaped the events of the preceding twelve months, the magazine’s process remains cloaked in a veil of intense secrecy, drama, and strict confidentiality.
As part of this rigorous production pipeline, TIME’s editorial staff commissions a select, elite group of visual artists, illustrators, and photographers each year. These creatives are tasked with depicting a wide array of potential "Person of the Year" candidates before the final decision is officially locked in. In an industry where leaks can undermine multimillion-dollar publishing cycles, the artists themselves are kept entirely in the dark. The final choice remains a tightly guarded secret, and commissioned creators rarely learn which portrait has been selected until the magazine hits newsstands and digital subscriber mailboxes worldwide.
For the historic 2020 Person of the Year feature—honoring then-President-elect Joe Biden and Vice President-elect Kamala Harris—the magazine tapped renowned Chicago-based illustrator Jason Seiler. Marking the second time Seiler was chosen to paint a TIME Person of the Year cover, the assignment represented a pinnacle achievement in contemporary caricature and editorial illustration. In an exclusive interview with Illustration Age’s Sam Gallant, Seiler pulls back the curtain on the high-pressure world of high-stakes political illustration, discussing the meticulous process of capturing the likenesses of world leaders, his unexpected passions outside of art—such as drumming—and the inner workings of working with one of the most prestigious editorial publications in the world.
Chronology: The Anatomy of a Top-Secret Editorial Commission
The journey from initial concept to a finished TIME cover is a grueling test of speed, adaptability, and artistic discipline. While the public sees only the polished final product, the timeline behind such a high-profile commission unfolds over weeks of covert preparation.
Phase 1: The Brief and the Blindfold
Weeks before the official announcement, TIME’s art directors reach out to a trusted roster of artists under strict non-disclosure agreements (NDAs). During this initial phase, artists are given a list of prospective candidates under consideration. For a presidential election year, this often includes the primary contenders, key political figures, or cultural movements that dominated the news cycle. The artists are asked to produce initial sketches or fully rendered paintings of these various figures without knowing which one will ultimately grace the cover.
Phase 2: Rapid-Fire Execution
Once the editorial board finalizes its selection—in this case, Joe Biden and Kamala Harris—the chosen artist must mobilize immediately. Because political news shifts by the hour, editorial deadlines are mercilessly tight. Illustrators often have mere days, or sometimes hours, to refine their preliminary concepts into a publication-ready masterpiece. For Seiler, this meant channeling decades of experience in digital painting and traditional caricature to capture not just the physical likenesses of Biden and Harris, but their distinct expressions, postures, and the gravity of the historical moment they represented.
Phase 3: The Global Reveal
The ultimate test of an artist’s patience occurs between the final stroke of digital paint and the public release. Artists like Seiler must maintain absolute silence, guarding files on encrypted drives while printing and distribution networks swing into action globally. The reveal happens simultaneously across digital platforms and physical newsstands, allowing the artist—often for the very first time—to see their work contextualized by headlines, yellow borders, and millions of readers worldwide.
Supporting Data: The Art and Commerce of TIME Covers
To understand the weight of Jason Seiler’s achievement, one must examine the legacy and cultural footprint of TIME magazine’s visual storytelling. Since its founding in 1923 by Briton Hadden and Henry Luce, TIME has utilized cover art not merely as decoration, but as a defining visual archive of modern history.
- Historical Precedent: While photography has dominated modern magazine covers, TIME has maintained a rich tradition of commissioning painted portraits for its most significant issues, most notably the Person of the Year franchise.
- The Evolution of Caricature: Artists like Jason Seiler bridge the gap between traditional fine art and satirical illustration. Caricature—long dismissed by some academic circles as lowbrow entertainment—has been elevated through digital mediums into a sophisticated tool for political commentary. By exaggerating key facial features while maintaining psychological depth, master illustrators can often capture a subject’s inner character more effectively than a standard photograph.
- The Digital Shift: Modern illustrators rely heavily on advanced digital suites (such as Adobe Photoshop and Corel Painter) paired with high-end pressure-sensitive displays (like Wacom Cintiqs or iPad Pros). This technological leap allows artists to make rapid, non-destructive revisions demanded by art directors operating in fast-paced 24-hour news environments.
- Seiler’s Pedigree: Based in Chicago, Jason Seiler has built an international reputation working for major clients beyond TIME, including Rolling Stone, GQ, The New Yorker, MAD Magazine, and various Hollywood studios. His previous TIME Person of the Year cover (featuring Pope Francis in 2013) cemented his status as a premier editorial portraitist.
Official Responses and Insights from the Interview
In his conversation with Sam Gallant for Illustration Age, Jason Seiler provided rare insight into the psychology of painting world leaders and balancing a multifaceted creative life. Below are the key themes and reflections drawn from their discussion.
On the Pressure of Painting Leaders
Painting political figures who are constantly in the public eye presents a unique challenge. Every nuance of a politician’s face is scrutinized by millions of voters, supporters, and critics alike. Seiler emphasized that successful political illustration requires looking past the superficial media image to find the human being underneath.
"When you’re painting someone like Joe Biden or Kamala Harris for a platform as massive as TIME, you aren’t just drawing a face; you’re drawing a symbol of an era," Seiler noted during the interview. "You have to balance accuracy with interpretation. If it’s too much of a straight photo-reference copy, it loses the artistic voice. If it pushes too far into distortion, it loses the dignity required for the office."
The Dual Life of an Artist and Musician
Beyond his accomplishments at the drawing board, Seiler opened up about his lifelong passion for music—specifically, drumming. Balancing the sedentary, highly focused nature of digital illustration with the physical, rhythmic energy of playing drums provides Seiler with a crucial creative outlet. He discussed how the two disciplines inform one another: both require an acute sense of timing, rhythm, structure, and intense concentration.
Navigating Confidentiality and Creative Freedom
Seiler also touched upon the realities of working under tight editorial constraints. While the mystery and secrecy add an element of thriller-like excitement to the job, they also require absolute professional discipline. Artists must trust TIME’s art directors, who serve as the crucial bridge between raw artistic expression and the overarching journalistic narrative of the magazine.
Implications: The Future of Editorial Illustration in Journalism
The inclusion of intricate digital paintings on high-profile magazine covers carries profound implications for the state of modern journalism and visual arts.
- The Value of Human Artistry in an AI Era: As generative artificial intelligence tools begin to flood the digital landscape with synthetic imagery, human-crafted editorial illustrations are experiencing a renaissance of appreciation. Works by masters like Jason Seiler demonstrate a level of intentionality, empathy, and critical thought that automated systems cannot replicate. A human illustrator understands the socio-political subtext of an administration change; an algorithm merely mashes pixels together based on prompts.
- The Evolution of Political Iconography: As political polarization deepens globally, the visual representation of leaders matters more than ever. Covers like Seiler’s 2020 TIME portrait help shape historical memory. Decades from now, historians will look back at these painted portraits to understand not just what politicians looked like, but how an entire culture felt during a pivotal transition of power.
- Empowering the Illustrator Community: Platforms like Illustration Age play an essential role in documenting the behind-the-scenes labor of commercial artists. By spotlighting creators like Seiler, the design community ensures that the public recognizes illustration not as an afterthought, but as a vital pillar of modern journalism.
As Jason Seiler continues to push the boundaries of digital painting, his work on the TIME Person of the Year franchise stands as a testament to the enduring power of illustration to capture, critique, and immortalize the human story.
To watch the full video interview between Sam Gallant and Jason Seiler, visit the embedded media player above or check out the archives on Illustration Age.