In Hilary Harkness’ application interview for the Yale Master of Fine Arts program, the artist recounts that the interviewer, who was an older man, told her that her work was boring. “Well, it isn’t for you,” she recalls saying. The interviewer reddened, but she got into the program. 

Since then, Ms. Harkness has been baffling viewers with paintings that are anything but boring. A gamine polymath who studied biochemistry at Berkeley — and is also a professional violinist — she burst onto the scene with hyper-surreal paintings of building cutaways that show tiny figures — pneumatic young women mostly — engaged in all sorts of sadistic and sexual mischief.

The staggering virtuosity of the painting itself — mannerist old master brushwork recalling Bosch but filtered through the sensibility of Leonora Carrington — made them impossible to resist.

The current show at the PPOW gallery springs from Ms. Harkness’s recreation of Winslow Homer’s historic Civil War painting, “Prisoners From the Front,” which she began copying in 2018. Homer’s painting depicts General Francis Barlow accepting the surrender of Confederate soldiers at Petersburg, Virginia. It is often referred to as the iconic painting of the Civil War, summarizing the conflict in a single image. 

In the copy, which is in the show, Ms. Harkness has effected a few sly transformations to Homer’s original. Barlow becomes distinctly more androgynous, if not outright feminine, with rosy lips, milky skin, and a slightly more curvy physique. A Union subordinate, standing next to the ragged Confederate prisoners, is depicted as Black rather than white. 

This shift in the subordinate officer’s race flies in the face of actual history, as Black Union regiments were strictly segregated from their white peers. The same with the gender of the general. Nevertheless, these shifts allowed Ms. Harkness to ask questions which then led to an alternate history centering on the idea of the original painting being commissioned, in Ms. Harkness’ imagining, by “a wealthy Black plantation owner” named Arabella Freeman.

And, Ms. Harkness added, “what if the fictional Black Union officer under Barlow’s command was not anonymous, but rather Charles Barlow, Arabella Freeman’s brother?” The myth of the Black Freeman family — and their complex relationship to the protagonists of Homer’s painting — was born. 

Ms. Harkness uses these pretexts to create a painterly soap opera that gleefully tweaks the racial and gender assumptions of the era. Arabella is shown striding proudly through her property, addressing plantation management while also navigating her budding romance with Justine, a white woman attached to the property, and also Barlow, who appears to be a woman passing as a man.

Her brother, Charles, the union officer, also has his challenges in situations rife with racial and sexual tension — he fathers a child with Barlow, which she then delivers in the middle of a battle in a deliciously absurd send up of historical war painting. Things progress, in other words, from improbable to surreal. The convolutions generated are so complicated, in fact, Ms. Harkness has provided a separate illustrated “zine” that helps viewers sort things out.

Ms. Harkness, in other words, revels in uncomfortable contradictions, improbable as they may be. Arabella is a Black plantation and slave owner, while her brother is a Black Union officer. Arabella pursues a relationship with a white woman and an androgynous Union general, with whom her brother has secretly fathered a child.

Ms. Harkness cuts away at the surface of history to divulge the churning fantasies just below the surface. We are looking at a possible future, but we are also looking at History’s Id. 

In the back-room Ms. Harkness focuses her whimsy on another era, the roaring Paris thirties and the tempestuous relationship between Gertrude Stein and Alice B. Toklas. Ms. Harkness’s gift for comedy is evident here. We see Stein, her squarish bare feet up on the table, flanked by her Picasso portrait, next to a glum Toklas staring off into space.

Josephine Baker also makes an appearance, resplendent on a massage table. A touch of macabre surrealism also appears in the form of a severed male head. It’s a send up of celebrity mythology and historical fantasy posing as history. 

Ms. Harkness reimagines history with witty and often disturbing panache, exposing the uncomfortable areas where our racial and sexual assumptions chafe against shifts in social reality. She also knows, as only a master painter can now, that fantasy is never that far from reality.