They were originally developed in 1990 by Microsoft by combining glyphs from Lucida Icons, Arrows, and Stars licensed from Charles Bigelow and Kris Holmes.
In 1992, only days after the release of Windows 3.1, it was discovered that "NYC" (New York City) in Wingdings was rendered as a skull and crossbones symbol, Star of David, and thumbs up gesture.
"NYC" in the later-released Webdings font was intentionally rendered as eye, heart, and city skyline, referring to the I Love New York logo.
[8] After September 11, 2001, an email was circulated claiming that "Q33 NY", which it claims is the flight number of the first plane to hit the Twin Towers, in Wingdings would bring up a character sequence of a plane flying into two rectangular paper sheet icons which may be interpreted as skyscrapers, followed by the skull and crossbones symbol and the Star of David.
[9] In the indie video game Undertale made by Toby Fox, a hidden character known as W. D. Gaster uses the Wingdings typeface to speak.