Landing in the Macintosh group as a bitmap graphic designer was a lucky break for me, and one interesting part of the job was designing screen fonts. It was especially enjoyable because the Macintosh could display proportional typefaces, leaving behind the tyranny of monospace alphabets with their narrow m's and wide i's.
The first Macintosh font was designed as a bold system font with no jagged diagonals and was originally called "Elefont." There were going to be many fonts, so we sought a set of attractive, related names. Andy Hertzfeld and I had met in high school in suburban Philadelphia, so we started naming the other fonts after stops on the Paoli Local commuter train: Overbrook, Merion, Ardmore, and Rosemont. (Ransom was the only exception—a font of mismatched letters intended to evoke messages from kidnappers made from cut-out letters).
One day, Steve Jobs stopped by the software group, as he often did at the end of the day. He frowned as he looked at the font names on a menu. "What are those names?" he asked. We explained the Paoli Local connection.
"Well," he said, "cities are OK, but not little cities nobody's ever heard of. They ought to be WORLD-CLASS cities!"
That’s how Chicago (Elefont), New York, Geneva, London, San Francisco (Ransom), Toronto, and Venice (Bill Atkinson’s script font) got their names.