There’s an immediacy to drawings that is not always present in paintings on board or canvas, which are often more carefully planned than their paper counterparts. Drawings allow an artist to sketch freely without worrying too much about how the final product will turn out. At worst, an unsuccessful drawing can be crumpled into a ball and tossed in the fireplace. At best, a good drawing captures an artist being unabashedly unfiltered and spontaneous.

Which is not to say that all drawings are necessarily scruffy, unpolished works. Indeed, many artists are as celebrated for their facility with a pencil or stick of charcoal as others are for their ability to apply paint with a brush or palette knife. To make the category even more difficult to pin down, many drawings feature paint stick, watercolor, and even elements of collage.

Drawings by artists skilled in draftsmanship are naturally highly sought. Winslow Homer (1836-1910) was a master of the sailboat at sea, which he could render just as convincingly in oil on canvas as charcoal and pencil on paper. M.C. Escher (1898-1972) used his pencils to produce optically coherent, if physically impossible, stairways to nowhere and other illusions—in one of his most famous drawings, a pair of hands appears to break the plane of the sheet of paper they have been drawn upon to draw each other. Saul Steinberg (1914-1999) also produced an image in which the hand upon the page appears to complete the artist's work (in Steinberg’s case, of a line-drawing self-portrait). But Steinberg was less concerned about his draftsmanship than the successful whimsy of his doodles, which often incorporated letters of the alphabet, numbers, and even punctuation to make their surreal points.

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