Walter Benjamin made the New Angel into an intellectual icon. The Angel Applicant by Paul Klee from 1939 is a different creature with nothing messianic about him. His eyes are downcast and blackened, looking at nothing past his own misery caught in time under the melancholy of a crescent moon. One expects nothing from him. Not blown by the winds of history, he is ugly and dog-faced.

As described here:

[Klee] covered a sheet of newspaper with black gouache on which he then drew the outlines of the figure and of the crescent moon with a thick, soft graphite pencil. Then he filled in these forms with a thin white wash. It is the black ground peeking through the white pigment that gives this creature its ghostly shimmer.