Month after month, a critic on the beat faces the same basic question: What to write about? At times I feel like Buridan’s ass, frozen by indecision, from which I am saved only by an arbitrary leap that I can’t explain even to myself. This month I want to talk about three gallery shows. How did I pick them? The explanation would be as roundabout as ever, except that this time I realized my quandary could be part of the subject.

It happened like this: Among the shows I spent a good bit of time with as I made my gallery rounds in September was one at Callicoon Fine Arts in the Lower East Side. Titled “Essays,” it was by Colter Jacobsen, an artist from San Francisco whose work I had not previously seen. The work was a kind of lyrical conceptualism—materially slight, emotional more than intellectual in tenor, very self-consciously in the lineage of Bay Area artists such as Bruce Conner and Wallace Berman. Later, I happened to exchange e-mails with Callicoon’s owner, Photios Giovanis, on another matter, and Photi, who had clearly taken note of my interest in Jacobsen’s show, added, “Of course I would love it if you wrote about it!” Usually I would let a comment like that pass without response, but somehow I decided to address it directly: Yes, I told him, I have in fact been thinking of writing on the show, but there are a few others equally on my mind and it will be a little while before I decide. That night, he replied, “Choose the underdog!”—adding that he assumed that could be Jacobsen.

Choose the underdog!—the phrase haunted me over the next few days. It touched a nerve. As everyone who follows the contemporary art scene knows, the market has been consolidating. A small number of mega-galleries have begun to dominate—threatening the very existence of the smaller and midlevel galleries, and therefore the livelihoods of the artists who exhibit in them. Now, just to be clear, as a viewer, I can hardly be all against the big galleries. Even if they have a tendency to highlight spectacle over substance, they also continue to put on the sort of in-depth historical shows museums ought to be doing, and they constantly draw attention to extraordinary contemporary practitioners. Still, it’s become more urgent to remind people of the vital work being done by artists struggling in the shadows of the new system. And besides, hasn’t it always been the case that artists inclined to explore the overlooked are themselves likely to be overlooked, at least in the short term?

In other words, Photi was right to consider Jacobsen—a mid-career out-of-towner having his first solo show in Manhattan show in a decade, with a gallery that’s highly respected but not exactly a market dynamo—an underdog. But what about the other artists I was thinking of writing about? Neither, as it happens, is well known in New York: one, Elizabeth Osborne, a Philadelphian painter in her 80s who last showed her canvases in New York more than 30 years ago, and who recently exhibited at a reputable Chelsea gallery that’s bigger than Callicoon, but nonetheless dwarfed by some of its neighbors; the other, Chelsea Culprit, an American living in Mexico City, who had her second New York solo show in a tiny gallery I’d never even heard of until a friend suggested I check it out. The venue turned out to be a small room in a Tribeca office building whose front door intercom I found so incomprehensible that I might never even have found my way in if someone hadn’t happened to be leaving the building while I was standing there flummoxed. Out of those three, I kept wondering, who would be the underdog?

Jacobsen’s art is a natural underdog. It almost seems to court the possibility of being overlooked—for instance, in this show, by deliberately leaving one piece off the checklist and hanging it over the door where many visitors wouldn’t have noticed it. Here, slightness and a sense of desuetude are prized characteristics. As the artist himself says, “I’d like to consider the power of smallness and the informal, the peripheral, the unfinished. Subtle like the ‘b’ in subtle.” Discarded objects found by the wayside are among his favored materials: things as mundane as empty, crushed cigarette packets (Fags for Joe & Bill, 2018), old photos and postcards, even simple bits of paper that happen to have the number 8 printed on them (Some, but not all, of my 8’s [from Uncle Steve], 2018). Rather than trying to work some visual alchemy on them, he seems content to examine their mundanity for its own sake. The works’ subtitles often indicate a personal meaning that might be irrecoverable to others—who is Uncle Steve, and what’s he have to do with the number 8? Yet Jacobsen’s found objects seem distinctly immune to sentimentality or nostalgia, either because of their very nature—not even the most committed smoker could feel a pang over his last pack of Marlboros, as long as he has the next one to hand—or because the artist’s blunt, unfussy treatment of his materials forestalls it.

Portrait Repair (Walgreens) (2008), for instance, is a diptych consisting of two photographs; one is an old sepia-toned portrait of a woman sitting with an infant on her lap, a young boy standing next to her with his hand on her shoulder. The picture is badly scuffed and a bit crumpled, particularly on the left side, where the boy’s face is almost completely obliterated. Next to this photo hangs a contemporary reprint, made—as the subtitle suggests—by the digital restoration service offered by the drugstore chain. In this case, though, the boy with the effaced countenance has been eliminated completely, as if he’d never existed—like a domestic version of Trotsky being expunged from the photographic record of a rally with Lenin. Maybe it’s the ultimate sibling rivalry fantasy inadvertently materialized—“how differently my life would have turned it if it hadn’t been for my big brother!”—but in any case, the piece understatedly conveys the cruelty of memory: We can preserve our recollections only by editing and transforming them.

Part of what makes Portrait Repair (Walgreens) so poignant is the nearly automatic process by which it was made—the fact that Jacobsen took its making out of its own hands, as if to display all the more objectively how “restoration” must always be a fiction in which something is sacrificed in order to salvage the rest. Maybe that’s part of why I’m less taken with a pair of graphite drawings with a similar theme: Trevi Fountain 1 (hippocampus) (2018) consists of two depictions of detail from the famous Roman landmark, a triton restraining a hippocampus, a mythological beast with the upper body of a winged horse on the lower body of a fish—though Jacobsen’s detail is cropped in such a way that they simply appear to be a man and a horse. The one on the left was drawn from a photograph, the one on the right, later, from memory—the main difference being that in memory’s version, the scene has been reversed, so that the two drawings mirror each other. There’s also a verbal pun at work here: As everyone who heard Christine Blasey Ford’s testimony to the Senate now knows, “hippocampus” also refers to a part of the brain that’s involved with emotion and memory. That memory can put us in a kind of mirror world is something to ponder, but the effect is nullified by the need for an explanation of how the piece was made—unlike the more immediately self-explanatory Portrait Repair (Walgreens).

But maybe I shouldn’t overplay the importance of memory as a theme in Jacobsen’s exhibition. The before-and-after format shared by Portrait Repair (Walgreens) and Trevi Fountain 1 (hippocampus) is featured in just a few of the works on view. In the larger context of the show, the point seems to be how noticing the differences among similar things activates attention—perceiving variation for its own sake as much as for any reconstruction of the process of change. Some of Jacobsen’s drawings are accumulations of tiny abstract marks that look like they could have been made in a trance, but they do convey images in different ways—for instance kiss (2018) is a close-up of a patch of grassy ground with some fallen leaves. One feels that the artist has looked at this little place so long and hard that it became a cosmos—but one on the verge of disappearance. He quotes the poet Tim Dlugos: “It / dissipates faster than / our eyes can record.” Jacobsen seems to want to record the dissipation itself.

Elizabeth Osborne’s exhibition at Danese/Corey was titled “People and Places,” and it featured recent paintingss she between 2014 and this year, along with a few from the 1960s. Her work, past and present, considers the vast terrain painting can open up between observation and abstraction. It’s a realm that’s been explored in part by many predecessors, from Henri Matisse through West Coast painters of the 1950s such as David Park; I also sensed affinities with Londoners like R.B. Kitaj and Howard Hodgkin: artists who felt the need to look for inspiration directly at the world—at people and places—but never intended to reproduce the look of them. Color, in this kind of painting, follows a logic of its own that intersects with real things at its own whim. In Osborne’s work, cool colors can burn with a searing intensity.

Really, the show might better have been titled “People in Places,” because most of the paintings grant equal status to the figure and the setting: Place has its own autonomous interest for the painter, and one usually feels she could have made a different painting, just as good, by leaving the figure out altogether. Occasionally the figure is half-concealed, almost not there. Studio (2014) is dominated by an array of vertical lines that I take to represent the edges of paintings in their storage racks; to the left is what seems to be the corner of a grayish landscape painting facing outward, and one just catches a glimpse of, presumably, the artist herself way in the background between her works.

The equality between people and places that Osborne’s paintings proclaim doesn’t mean that she paints them in the same way; at times it’s as if she’s using two different pictorial dialects. Places are apt to come to life as broad, freely and fluidly brushed-in color zones, quite flat. Bodies and faces are granted not only more detail—though not much by the standards of old-fashioned realism—but above all, more volume. Sometimes that means the transitions between parts of the composition feel a bit rough.

Consider Audrey Seated (2014): The portrait subject, looking out at the painter with a certain distrust, it would seem, is tiny in proportion to the space in which she sits; the four-paned window behind and above her is the piece’s main subject. She is the counterpoint, and she’s squeezed into the corner of long couch that, strangely, appears to be bisected by the mullion of the glowing yellow windows above. Or maybe the reason it seems strange is that something else is going on altogether. It could be that she’s sitting on a blue chair set at an angle, and the gray passage represents the wall beneath the windows (though the rest of the wall is not gray) and the white vertical is a curtain rather than a mullion? The ambiguity shows that Osborne is less interested in description than in abstract composition. But there’s a psychological upshot to that abstraction: The blue arc of the couch’s arm simply cuts off Audrey’s body at the waist, as though there is no space for her dimensionality in a world transmuting into nothing but luminosity and color. That’s the painting’s essential underlying strangeness. At first it seemed a miscalculation, but somehow the disconnect or dissociation between the painting’s parts held my attention—and finally I had to accept the discord as the painting’s essential feature, its way of finding the animating energy within what might otherwise be the blandly beautiful surface of things.

Jacobsen’s art takes a chance of being too elusive or insubstantial, Osborne’s of stopping short at a superior loveliness; those are not chances Chelsea Culprit is willing to take. For the subdued everydayness the other two cultivate—Jacobsen with found objects and the banal act of copying, Osborne through the depiction of a tranquil middle-class domesticity—Culprit substitutes a sort of trashy glamour I find equally seductive. Culprit is the artist whose work I found at the Tribeca gallery Queer Thoughts, with four big works installed chockablock in a tiny space (and another could be seen in the sliver of a back office space) in an exhibition titled “DMing Purgatory.” Facing the door were two big paintings—each about five by eight feet—hung one atop the other, touching. Actually, they were more drawn and colored in than, in any strict sense of the word, painted, but they were rendered with complexity and gusto. In any case, one might have thought the two works were one great diptych, or then one might on the contrary see them as three different works, since the painting hanging on the bottom in itself was really was a diptych on two canvases. Where did one painting end and another begin?

I don’t think I’m just quibbling about this question of how many paintings there were, because the question of “how many” was part of the question being posed within the canvases too. They seemed to enmesh, in a quasi-Cubist manner, many iterations of a female figure doing some impossibly pretzel-like dance moves while wearing outrageously high platform shoes. But was I meant to see them as many dancers, or multiple views of the same dancer? The paintings invite the viewer to untangle the fragmented and intertwined bodies and account for all the pieces, even if the works’ titles, High Spirited Chimeras With Hypnotic Digital Masks I and II (2018), warn that any such conclusion might be illusory.

On two facing walls were another pair of matching or complementary works, Butterfly Moth in Transcendental State and Black Widow Anarchist Hourglass (both 2018), which might best be described as shaped-canvas relief constructions, made from colored fabric, hardware, and belts. Their imagery continues that of the two paintings: legs, feet, platform shoes—but in contrast to the unending energetic swirling of body parts in the paintings, the ones in these symmetrical and geometrically ordered pieces, seemingly locked into place by chains or belts, suggest a pose that is held fast and transformed into a symbol.

But what’s the symbol of? Either power or powerlessness—or maybe just the performance of them. Again, as the canvases’ sweeping dynamism leaves me in a state of doubt, so does the declarative simplicity of these wall reliefs. What Culprit risks, unlike Jacobsen or Osborne, is an art that’s too blatant, too in-your-face—but then that blatant art turns out to be as elusive or reticent as the others. Online I found a 2014 interview with Culprit—who was then going by the less unlikely name of Chelsea Culp—in which she was asked about what she wanted her work to give its viewers. Her response—“I like when sensitivity to nuance makes it difficult to say what something is”—could as easily have been the answer given by Jacobsen or Osborne.

That hidden connection, the fascination with the transitory aspects of perception that evade articulation, probably explains what attracted me to the work of three artists otherwise so different. But it doesn’t answer the question I started with: Who’s the underdog? Well, I don’t think it would have been much of a spoiler if I had told you straight off: all of them. The other day, when I mentioned that his plea, “Choose the underdog,” had inspired my next article, Photi looked embarrassed and told me, “Actually, it wasn’t me saying that. When I e-mailed you I was with Colter in San Francisco—he’s the one who said you should choose the underdog. I just added that I thought it should be him.” Jacobsen wasn’t pleading for himself, but for any artist working against the odds by looking for things that are, as he says, as subtle as the ‘b’ in subtle. And if you find it, what then? I think again about what Dlugos wrote: “It /dissipates faster than / our eyes can record.”