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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.

I do agree on all other points :)

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Pretty sure it was Charcoal and not Geneva.

You're right, I mixed up the two font names in my head. I edited my post above.

Huh, TIL. I had always thought it was always just up-res'ing variations on Chicago, up thru and including the first iPod.

They look pretty similar but now that I look it them side by side I see it a bit.

As much as it is the style, it's also that kinda.. not-True-type still-a-bit-pixelated edges look that is the nostalgia factor, I guess.

Original iPod did use Chicago though! Then when they got color screens they switched to Lucida Grande.

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.

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