John Currin made his name by challenging core beliefs of postwar avant-garde American art—among them, the belief that the art of the past had nothing to teach the present; that commerce was evil; and that the male artist should avert his prurient gaze from naked women. As the fascinating survey show at DHC/ART made clear, he left no taboo unviolated. It helped that Currin—by his own account, an angry, ambitious young man—had a taste for rebellion and understood the possible commercial appeal of playing the enfant terrible. Still, it took nerve for any aspiring artist, let alone a 1986 Yale MFA graduate, to pursue figurative painting in the heyday of political correctness. Not only had the medium been famously pronounced dead, but few art schools taught the requisite skills in any depth.

The DHC/ART exhibition charts his remarkable trajectory from klutzy dabbler to virtuoso. At first, his subjects are loser guys and melon-breasted women, rendered with the cartoonish modelling, repellant colours and heavily impastoed paint-by-numbers techniques characteristic of the so-called Bad Painting movement. Notable from this period is Ms. Omni (1993), one of a series of imperious aging society women with jutting bones, torqued necks and hawkish gazes—a harbinger of his signature mannerist distortion.

His early daubings gave no formal clue that Currin would soon be haunting the Metropolitan Museum of Art in an attempt to emulate the Old Masters. One can scarcely believe that four years after painting The Wizard (1994) (which shows a childlike clown reverently laying his black-gloved hands on a smiling woman’s huge breasts), he created Honeymoon Nude. The sensitively modelled, satin-skinned sylph is based on his wife, the artist Rachel Feinstein, and belongs in a charmed league with the pot-bellied Venuses of Lucas Cranach the Elder.

Paintings of Feinstein, such as Honeymoon Nude and the bewitching Rachel in Fur (2003), invariably endow their female subject with a Renaissance air of calm, mysterious intelligence. At the other end of the spectrum are Currin’s portraits of generic American pin-up girls as seen through the eyes of horny adolescents and goddess worshippers. These semi-satiric portrayals of sexual fantasy and class affectations are arresting—even amusing—but often empty of feeling. The images recurrently feature a girl-next-door who is both wholesome and sexually available; this trope is exemplified by Big Hands, a 2010 painting of a Breck Girl blonde with half-parted lips, vacuous stare and greatly exaggerated torso. A much-discussed series of paintings based on pornographic imagery misfires into an awkward, unerotic jumble of private parts; when asked to explain the project in interviews, Currin sounds vague and clueless. The artist knows how to grab a viewer’s attention (no mean feat), but it is not always clear what he wants to say.

Currin has been called a shallow opportunist who plays postmodern games for the delectation and titillation of the super-rich. Jed Perl, the art critic for the New Republic, has pointed out (rightly) that Currin is no match for Renaissance masters as a painter—yet surely it is enough that his increasing mastery of underpainting, brushwork, glazing and other hoary tricks of the trade have enabled him to pull off such intriguing tableaux as Thanksgiving (2003), a surreal Norman Rockwell scene rendered as if by Jan van Eyck. In the painting, rapture and dread vie for supremacy as a lively young woman lifts a silver spoon to the open mouth of a golden-haired beauty; below, a melancholy older woman bows her head, while a sinister raw turkey sits glistening in a pool of blood on a platter.

Although he sometimes loses his way, Currin’s quest to find beauty, even in that which is foolish, troubling and sordid, strikes me as authentic—and generous. At his best, he puts art history back into play, not to vaunt his skill but to reclaim a priceless Western tradition of pictorial intelligence and sensuous pleasure. His odd imagination and formidable discipline will likely continue to offend, mystify and delight.