Willem de Kooning mostly drew women, and his relationship to both — subject and medium, that is — was fiercely ambivalent. This was luck for drawing, if not for women.

A fine selection of works on paper at Allan Stone Gallery spans a half-century from de Kooning’s student days to the mid-1970s (he died in 1997), and, although it includes mostly smaller and slight works, the show affords a vital sense of what drawing meant to him.

His ambivalence had a great deal to do with facility. The Dutch-born Abstract Expressionist was preternaturally talented, and, having attended the Rotterdam Academy of Fine Arts and Techniques, well grounded in tradition. Drawings in a neoclassical hand that recall Ingres, such as the drawing of a female head inscribed “To my very dear sister” and dating from the 1930s, or a superb, at once meticulous and expressive “Portrait of Elaine” (1940–41) exude old-masterly finesse, seemingly breathed onto the page with incredible variety of touch and dexterity.

But de Kooning was after more than finesse. Contemporaneous with these tours de force are scratchy, scribbly efforts such as “Seated Woman” (c. 1941), which are energized by a knowing awkwardness. This drawing, in itself, encapsulates ambiguity. You can see a disintegration of intent in its manifest history: The head and breasts, though schematic, are rendered in gentle, soft, circular motions. In the shadow around the breasts, for instance, you can sense tender deliberation. But then, imposed as if in a sudden attack of impatience — if not something worse — is a frenzy of fast and furious lines where the graphite is crude and emphatic. It is as if Mr. Hyde burst upon Dr. Jekyll to complete the doctor’s drawing.

Sexual ambivalence is signaled at the outset of this show with a remarkable youthful work, “The Kiss” (1925), a symbolist image that roots his vision in Edvard Munch and, to a lesser degree, Jan Toorop. The drawing shows lovers locked in embrace, the mouths forming a deliberate graphite blur. The girl’s highly stylized fingers rest longingly on the boy’s shoulder. In a slow, built-up composition, layers of graphite produce a crepuscular glow. There is a sense of the receding seashore following the undulations of the lovers’ faces.

An untitled 1939 portrait of a seated woman — more unified in language than the slightly later drawing described above — relates very closely to similar drawings by de Kooning’s friends Arshile Gorky and John Graham (also seen recently at Stone) and to his own paintings of the 1940s. The convolution of the woman’s left arm and hand, and the sense that she is turning this limb in real space and that the artist is twisting it on the page reinforce the roots of modern Expressionism in old masterly mannerism. There is pent-up energy in that hand, a strange mix of pain and elegance, of angst and gesture.

There was great fluidity between drawing and painting in de Kooning’s activity, and for all that the works here are sketches, ancillary or anticipatory in relation to well-known canvases, there is a sense, too, of equality among media. “Study for Pink Angels” (1945) is a superb work, easily the sexiest in the show. In its surreptitious presentation of limbs in movement and simultaneous view of different angles and gestures, it exemplifies de Kooning’s whole philosophy of the suddenly chanced-upon image, “a glimpse of something, encountered like a flash.” Here the flesh is denoted by yellow pastel, the only color on the page; in the painting, the figures are pink, in lurid contrast to the yellow ground.

“Abstraction (Study for Mailbox)” (1945) underscores the way in which, in breakthrough black-and-white paintings of the next few years, such as “Painting” (1948) in the Museum of Modern Art, a jigsaw-like linear network would be abstracted from specific, observed shapes. Unlike Jackson Pollock or Mark Rothko, de Kooning very rarely capitulated to pure abstraction: However hermetic his sources, he was grounded in some level of observed reality.

While structure can be discerned even in his most gestural and color-led paintings, his later drawings exude a kind of mark-making that can only be described as painterly. “Untitled (No Fear but a lot of Trembling)” (1963), which inscribes this humorous reference to Kierkegaard under a highly perfunctory, sketchy reclining figure, deploys exquisitely mushy charcoal lines in a way that is soft and fast. There is a calligraphic quality to the line, like handwriting, and yet, despite the way the lines are jagged and broken up, there is an organic unity, and flow, in this evocation of feminine presence.

The largest and latest work in the show is a double-sided, untitled charcoal drawing with drubbings of oil paint on translucent vellum: The frame, freestanding, is a dramatic presence in an otherwise highly refined installation. It is, however, a slight work, although in its speed and semiconscious structure it is an interesting throwback to de Kooning’s compositional mode of the 1940s. It relates, also, to his sculpture of this time, which combines frenetic improvisation with underlying structure. What is remarkable through his body of drawings is the way he is able simultaneously to outline forms and suggest their locations in space.

In the eloquent and persuasive catalog introduction, Donald Kuspit explores this duality, observing how line can denote volume while at the same time emphasizing the flatness of the picture plane. Mr. Kuspit relates this to twin but battling art-historical influences: the unconscious doodling of Surrealism and the highly ordered spatial complexity of Cubism. It results, Mr. Kuspit argues, in “a sort of free-floating yet form-inventing line, simultaneously analytic and synthetic in character.”

This show follows a slew of exhibitions marking the 10th anniversary of de Kooning’s death, including sumptuous displays, at L&M Arts (until this weekend) and Gagosian Gallery last month, of the problematic yet delectable paintings from his years of senile dementia. It also celebrates the close association of de Kooning with Allan Stone, who died last December, as it is the 11th show of his work at the gallery since the two-person show de Kooning shared with Barnett Newman in 1962.

Until December 22 (113 E. 90th St., between Park and Lexington avenues, 212-987-4997).