Wingdings: (1) Why? (2) Wait...what?
Wingdings are the computerized representation of dingbats. These decorative marks, also called printer's ornaments, are used in typesetting to add spaces, borders, and section breaks.
In the early days of word processing, adding non-text symbols to a document was essentially impossible. Wingdings fonts made more characters representable by mapping all text-based characters to three sets of symbols. Crucially, these symbols could be scaled and weighted, like any other font.
Microsoft, when creating Wingdings, probably didn't expect people to use this weird new font to type random stuff like, say, the name of the most famous American city:
Not good. Very bad.
Despite complaints about this unfortunate mapping, Microsoft left it unchanged to maintain backwards compatibility with earlier Wingdings users.
When they got their next chance, adding more Web-related symbols in the Webdings font, they compensated by making a rebus puzzle:
Footnote 1: The post above was 140 words long. There are 140 days left in the year.
Footnote 2: The answer to the rebus puzzle is the state slogan, "I Love New York"