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This is a very tough call. I love Chicago, as it is such a huge part of the early Macintosh UI (also the early iPods). New York was my default word processing font until OS X became my primary operating system. All of those old Susan Kare fonts were special in their own way. However, I'm going to go with Bill Atkinson's Venice here. I always used this as a heading font and have yet to find a font as beautiful for that purpose.
I love Chicago, mostly due to its use as a system font before OS 8 (as mentioned by Scott). Secondly, I'd have to say either New York, or Avant Garde (not a font that came with the OS, but an Apple font all the same - from memory it was distributed with StyleWriters, and most likely with other imaging devices as well)
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