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We present a fully automatic method to generate detailed and accurate artistic shadows from pairs of line drawing sketches and lighting directions. We also contribute a new dataset of one thousand examples of pairs of line drawings and shadows that are tagged with lighting directions. Remarkably, the generated shadows quickly communicate the underlying 3D structure of the sketched scene. Consequently, the shadows generated by our approach can be used directly or as an excellent starting point for artists. We demonstrate that the deep learning network we propose takes a hand-drawn sketch, builds a 3D model in latent space, and renders the resulting shadows. The generated shadows respect the hand-drawn lines and underlying 3D space and contain sophisticated and accurate details, such as self-shadowing effects. Moreover, the generated shadows contain artistic effects, such as rim lighting or halos appearing from back lighting, that would be achievable with traditional 3D rendering methods.