The original Macintosh interface was drawn one pixel at a time in black and white, and its icons had a personality that later, higher-resolution systems never quite recovered — the smiling Mac, the bomb, the watch, and a long tail of stranger images from utilities, extensions and error dialogs that people still recognize decades later without being able to name where they came from.
This hat
I have been seeing this old Reaper icon from an earlier Mac OS floating around the web, and I became obsessed with it. I really love it. If you know what it might be from, please let me know!