Self Portrait 1993
1993
Surrealism
22" x 22"
55.9cm x 55.9cm
Status & ownership
Private collection
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Contribution
Self Portrait 1993 is the origin point of Bolter's practice — made before art school, before the transfer technique, before the series framework. Its formal contribution is modest in the context of what came after, but historically it is the first evidence of the instincts that would drive the whole body of work: the surreal cohabitation of interior and exterior space, the interest in how a single image can hold multiple moments and meanings, and the self as a subject approached obliquely rather than directly. The sideways eye, the window, the hand — all of it points outward, away from the room. That orientation away from the immediate and toward something beyond turns out to be the structural logic of every series that followed. A later reading, produced by pairing the catalogued record with an independent AI vision analysis (July 2026): the two disembodied forms are the painter's two instruments. The head with its single watching eye and the hand resting at the windowsill — eye and hand, seeing and making — portrayed as separate objects by a self-taught nineteen-year-old at the exact moment of teaching himself to use them together. The vision analysis, knowing nothing of the work's context, offered 'a figure contemplating its own dismembered instrument' as one reading of the head-hand relationship; the record's context resolves it. A self-portrait of the painter as his own tools, before the practice existed to unite them.
About the work
Oil on raw, self-stretched canvas, painted in a covered backyard in San Francisco's Sunset District on the artist's birthday in 1993. A surreal self-portrait: an oversized head wearing a baseball hat, a single sideways eye, a disembodied hand on a windowsill, and a green sky with tree branches beyond the grey interior. The first in a birthday self-portrait ritual that continued for three years. Painted on the artist's birthday in 1993 in a covered backyard space at the family home in San Francisco's Sunset District, Self Portrait 1993 is one of the earliest works in the OG oil paintings — made on raw, unprimed, self-stretched canvas by a self-taught painter who had never read a book on how to make art, only on how to look at it. The composition places an oversized head — wearing a baseball hat, with a single blue eye looking sideways — in a spare grey interior. A disembodied hand rests on a windowsill; beyond the window, a green sky and bare tree branches reach outward. The surreal vocabulary comes directly from the artists Bolter was absorbing at the time: Dalí's dreamlike scale distortions, Magritte's interior/exterior logic, Tanguy's atmosphere and colour, Klee's flattened figure-making, and the fractured viewpoint of Picasso's Cubism in the sideways-looking eye. The painting was also a deliberate turning away — from the slick graphics of skateboard culture Bolter had grown up with and loved, toward something older, more interior, more European. The reading that preceded the painting — Nietzsche, Goethe, Sartre, Henry Miller — was a post-school self-education, painting a way of joining that conversation on his own terms. Shown once in a neighbourhood café shortly after completion, the work has remained at the family home since. Looking at it now, Bolter identifies a yearning in the composition that he couldn't have named at the time: the window, the outside world, the gaze directed away. He had only ever lived in San Francisco. He would eventually travel widely. The painting, made before any of that, seems to already know it.
Art/Official sessions
Self Portrait 1993 — Art/Official session, June 1, 2026
This is a copy of the session record, June 1, 2026. Canonical URL: /sessions/self-portrait-1993-2026-06-01.
Transcript
- Artist
this is one of my oldest paintings, its a self portrait from 1993 done with oil on canvas. the painting is 22" x 22"
- Art/Official
Good to know — one of the originals.
- Art/Official
Is this part of something ongoing, or does it feel more like a standalone moment?
- Artist
its part of my origial OG paintings that I did in oil paint. after high school I started to read a lot of liturature and about art and decided I wanted to start painting, so I got cnavas and oil paint and started these paintings. did really know what I was doing, so most paintings were on raw canvas that I would strech and just paint with oils. didn't know what I was doing, but it worked itself out and was the spark of it all
- Art/Official
That's a real origin story — the whole practice starting from raw canvas and figuring it out as you went.
- Art/Official
Where were you when you made this one?
- Artist
back at my parents house in the sunset district in San Francisco



