Kare’s first assignment was developing fonts for the Mac OS. At the time, digital typefaces were monospaced, meaning that both a narrow I and a broad M were wedged into the same bitmapped real estate — a vestigial legacy of the way that a typewriter platen advances, one space at a time. Jobs was determined to come up with something better for his sleek new machine, having been impressed by the grace of finely wrought letterforms in calligraphy classes he audited at Reed College, taught by the Trappist monk Robert Palladino, a disciple of master calligrapher Lloyd Reynolds. (The lasting impact of Reynolds’ instruction can also be seen in the playful cursive of the seminal West Coast Beat poets Gary Snyder and Philip Whalen, making Reynolds and Palladino the human hyperlinks between desktop publishing and Jack Kerouac’s Dharma Bums.)
For the Mac, Kare designed the first proportionally spaced digital font family that allowed text to breathe as naturally on the Mac’s white screen as it does in the pages of a book. The distinctive Jobs touch was upgrading the original monikers of these elegant typefaces from the names of train stations near Philadelphia — like Rosemont and Ardmore — to those of world-class cities like Geneva, Chicago, and New York.