I read online somewhere that Burt Lancaster, playing J.J. Hunsecker the monstrous Broadway newspaper columnist in 1957’s The Sweet Smell of Success, wore the “most evil glasses in movies.”
They were a standard late-‘50s design with hornrims on the top half and underwire below. They are currently the most popular “hipster” glasses in Brooklyn, or were a few years back. They oddly magnified Hunsecker’s malevolence in the movie: Lancaster without glasses wouldn’t be the devil he is with them on his nose.
I kinda agree with this estimate, although I also lean toward Doctor Caligari’s specs. Just because…you know, it’s CALIGARI.
Do sunglasses count as “eyeglasses?” If so, there are none more evil-looking than those adorning the cold, hard visage of…The Man with No Eyes.
Does TV count as “cinema”? If so, dare to stare into the face of one of Gotham’s most dastardly literary terrors…Bookworm!
(IIRC, the lenses were so thick, Mr. McDowell could not see out of them and he is generally shown being helped by other cast members when he has to move around in the episode.)
Mr. McDowell obviously had an affinity for striking e-ville poses with spectacles, as can be seen from this candid shot…
If you want to open it up to literature as well as cinema, how about the dark glasses worn by the man who was Saturday in G. K. Chesterton’s The Man Who Was Thursday:
Robert Prosky as The Judge in The Natural (1984). He’s clearly supposed to be The Devil, and in most scenes you can’t see his eyes because of his glasses. But unlike other cases of glasses obscuring the eyes, his glasses aren’t dark or mirrored – they are always simply angled to reflect whatever light is in the room.