
When I meet Oliver Osborne at Francis Irv on a rainy afternoon in May for coffee, I am immediately struck by the degrees of self-trust he has in his practice. “The history of painting in England does not interest me,” the Edinburgh-born artist replies when I ask him where he draws influence. Osborne is a painter who is always looking elsewhere. He received his art education in London before relocating to Berlin a decade ago where he has lived ever since, creating mysterious, semi-private, and medium-specific paintings—his most recent of his own children are his most intimate.
Upon entering the downtown gallery’s mix-used building, which still retains that old Chinatown grunge, I immediately see Comic Sans, 2025, with the title (also the exhibition name) spelled out in standard black letters against monochrome yellow on linen. The typeface is unevenly rendered, with smudges revealing the undertone of the fabric. The work operates as a doubled meaning with deadpan humor: a nod to his earlier paintings, minimal and cerebral, and riffing on language and culture. It is this kind of conceptualism that has driven Osborne’s painting throughout the 2010s, often resisting easy categorization. For the past four years, however, he has been thinking about a new context, namely classical portraiture and what it means for a contemporary artist to affiliate oneself with a historical image culture.

Osborne is not just interested in the devotional labor of painting, scraping on herringbone linen, but the essential question: Can 21st-century painting transcend time? To this end, most paintings in “Comic Sans” feature two of his three sons, depicted in classical style as if culled from Renaissance paintings. Family images and historical associations couple and decouple in references that expand and contract across time and space.
In Untitled (May), 2024-2025, Osborne’s 10-year-old son, Wolf, gazes outward, like a sitter from 15th-century Italy; he is inquisitive and yet somewhat awkward. His skin color, a mix of heavy yellow and red, lacks naturalism, and his face appears to be a mask refracted through light, bordering artifice. Another portrait Untitled, 2025, similarly depicts the same child’s face in gradients of green and yellow. With a color palette evoking Old Masters and a staunch refusal of high fidelity, each painting’s laboriously considered surface is a site where the artist contests how certain art-historical tropes are considered part of our eternal cultural inheritance.
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Repetition accrues difference until it reaches an emotional height in Multi-Figure Composition, 2024-25, where fragments of the artist’s children posing contemplatively blend into each other. The foreground and the background become a foggy, flat totality. Time is hauntingly disjointed, as the painting knows no past and future, collapsing all figures into the eternal present.
Across the Atlantic, concurrent to “Comic Sans” is another solo show by Osborne at London-based gallery Union Pacific, titled “Ooh!” For this exhibition, Osborne’s paintings reference other iterations and, in this sense, enter call-and-response with his series in New York. The works shown in London also feature Osborne’s sons, as well references to Filippino Lippi, the Italian Renaissance painter who was more celebrated for his technically sophisticated mimicry than his originality. Lippi’s portrait of an unnamed Florentine noble young man from around 1485 becomes the source material for Osborne’s Portrait of a Youth (after Filippino Lippi) III, 2025, a hazily rendered half-face, perhaps that of Osborne’s son, peeks out from the right shoulder of Lippi’s unknown youth, again reminding us of the painting’s departure from reality.

Now back in his studio in Berlin, Osborne is working toward a solo exhibition at Italy’s young, edgy alternative space ICA Milano in the fall. The exhibition will hone in on his recent painting The Sleeping Guard 2025, a divided composition based on the artist’s 7-year-old, Alfie, posing as a sleeping guard from Piero della Francesca’s fresco The Resurrection of Christ, c. 1460s. As he continues to think through the conceptual play between division, symmetry, and order, Osborne continues to filter through time, hinting at what remains evocative and what fails in our long history.
“Oliver Osborne: Comic Sans” is on view until June 14, 2025 at Francis Irv at 106 Walker St.Suite 201, New York, NY 10013.