I'll be that guy... the system font for menus, etc in OS 8 and 9 is "Geneva" [EDIT: It's "Charcoal", of course. Thanks for the heads up!]. It was "Chicago" up to and including System 7.x.
iPod used Chicago for the same reason Chicago was used on the original Mac—it was designed to make UI elements clearly readable on low resolution monochrome screens.
I do agree on all other points :)