Charline von Heyl: Blacksmile, 2013, oil, acrylic and charcoal on canvas, 82 by 78 inches; at Friedrich Petzel. 

"Schadenfreude," the German word meaning "pleasure taken from another's misfortune," came inescapably to mind upon encountering Blacksmile (2013), the first of 14 paintings in Charline von Heyl's recent exhibition. Indeed, the term points to the intricate syntax of the German-born artist's best work.

Known for being stylistically idiosyncratic, von Heyl subverts our expectations both of the nature of painting and the nature of her painting, constantly undermining conventional aesthetic judgment. Whether a particular painting pleases or annoys, she forces us to scrutinize the validity of our criteria.

is straightforward but ambiguous on every level. Our initial impression is of coal-smudged geometry on an ocher ground. The upper black corners frame a curved yellow form that is bitten into below by a smutchy hybrid shape, consisting of the Cupid's bow of an upper lip and an eccentric rectangle: the black smile of the title. The curved yellow form could also be seen as a blonde coif surrounding a blindfolded face. The colors and formal uncertainty create a sense of goofy menace, evoking a jack-o'-lantern, with a nod to the Batman logo. Perhaps Blacksmile embodies the schadenfreude von Heyl experiences at our difficulty in navigating the mass of contradictions of her paintings.

The ambiguities of figure and ground, abstraction and representation, soft and hard, goofy and menacing contained in Blacksmile are familiar confusions and easily assimilated through the pleasure of her pellucid paint handling. These same sets of uncertainties animate paintings like Night Doctor (2013). At the bottom of a loosely painted pink canvas, a series of black parabolic forms can be seen as a rubber-gloved hand pawing uneasy flesh.

But then there is Bois—Tu De La Bier? (2012). Like Blacksmile, it is yellow and black, but here a flat, glowing primrose lager provides the ground for scratchy black lines, which limn the borders and protrude into the center like a yapping dog tied to a tree. Bois—Tu consists of only acrylic paint, whereas usually von Heyl softens the hard acrylic underpainting with oil colors. 

The title could imply, "Do you have a taste for a dry, bitter painting?," as if one's aesthetic were a mere physiological preference. For von Heyl, the fingernails-on-blackboard mood conjured by this painting is simply the result of one of her arbitrary stylistic choices and is no more peculiar than any other. But this work also highlights a struggle between artist and viewer over the limitations of a painter's investigations.

After repeated viewing, certain paintings in the show simply seemed aesthetically insufficient. We're not engaged on enough levels by the pat iconic resolutions of paintings like Bois—Tu or Skull (2012), in which a densely brushed dark field is resolved into a skull shape by the hard-edge overpainting of an opaque white and yellow ground. The dialogue of such paintings with the more complex works felt superficial; they seem to have been created to provide a foil, rather than as part of a complete proposition.

Von Heyl's best works navigate painting's twin conditions of arbitrariness and specificity, and establish a pictorial space that rejects dogmatic flatness. They do not use representation to describe the world, or even to depict the artist's relationship to it. Instead, representation establishes the mood of her own problematic relationship to painting, its history and the people who view it.