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We rarely talk about comedy in painting — but if ever there was an artist having fun with the medium, it’s Portland’s brilliant, hilarious Stephen O’Donnell.

O’Donnell’s witty self-portraits turn gender on its head, sabotaging period detail in the process. The self-taught artist’s favorite ploy is to depict himself in elaborate 18th-century drag, with five o’clock shadow and chest hair in plain view.

O’Donnell’s acrylic-on-panel brushwork, almost photorealistic in technique, is exquisitely nuanced and controlled. But the visions he summons of himself are anything but straightforward.

His new show at Winston Wächter Fine Art, “Told and Untold Stories,” includes plenty of “18th-century” O’Donnells. The artist appears in rare male finery in “C’est mon chapeau” (“This Is My Hat” — and what a hat it is!). Everywhere else he’s in Marie Antoinette mode.

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“Une Petite Pause” (“A Little Pause”) depicts the painter supposedly taking a break from his work. He’s tilted back on his chair, shooting a cocky sidelong look at the viewer. His elaborate gown and lofty hairdo aren’t like anything most artists would wear in the studio. A thin paintbrush juts up at a phallic angle from his lap, thoroughly confusing the gender signals.

“Les Amies, Les Amants” (“Friends and Lovers”) is elaborate in a different way. It shows O’Donnell and his wife in voluminous gowns, peering from a series of five doorways in a long corridor.

Above one doorway is the bottom half of a painting-within-a-painting depicting a kneeling, lovemaking couple glimpsed from the thighs down. A skull at their left and a doll’s head at their right add a memento mori touch. The overall effect on the viewer is of falling vertiginously into a Byzantine private world.

Elsewhere O’Donnell ventures into other centuries. “Le Voile” (“The Veil”) is a shadowy affair, with O’Donnell clad in a dress so stiff it looks upholstered. The period appears to be the late 19th century, and his pensive gaze brings to mind the doomed Lily Bart from Edith Wharton’s novel “The House of Mirth.”

In a trio of works titled “The Judgment of Paris,” O’Donnell seems to be channeling his inner Joan Crawford (in paintings subtitled “Hera” and “Athena”) and his inner Joan Fontaine (a radiant figure flanked by soaring white doves in a painting subtitled “Aphrodite”).

The 1940s hairdos bring out a tougher side of O’Donnell, especially in “The Judgment of Paris: Hera.” The goddess, who was rejected by Paris in favor of Aphrodite, is paired with a peacock that seems to be loudly protesting her choice of dress (it’s decorated with peacock feathers). Between the bird’s all but audible squawk and Hera’s lidded, remonstrative eyes, there’s some serious comic tension here.

The show’s finest piece may be “Infanta,” an homage to Velázquez. O’Donnell, of course, is the princess of the classic painting, all grown up now, with a pet monkey to keep him company and with the inevitable sprinkle of chest hair peeking out over his low-cut gown. Every detail here — O’Donnell’s crookedly pursed lips, the elaborate folds of fabrics he’s wearing, the smug contentment in the monkey’s gaze — rewards a second careful look.

The playfulness of O’Donnell’s “Told and Untold Stories” has its spooky side too. It isn’t just his maverick choices of subject matter, but the finesse he brings to his task that makes the best of these works feel like masterpieces.

Michael Upchurch:

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