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Wingdings is a series of dingbat fonts that render letters as a variety of symbols. They were originally developed in 1990 by Microsoft by combining glyphs from Lucida Icons, Arrows, and Stars licensed from Charles Bigelow and Kris Holmes.[1] Certain versions of the font's copyright string include an attribution to Type Solutions, Inc., the maker of a tool used to hint the font.

None of the characters were mapped to Unicode at the time; however, Unicode approved the addition of many symbols in the Wingdings and Webdings fonts in Unicode 7.0.[2][3]

In 1992, only days after the release of Windows 3.1, it was discovered that the character sequence "NYC" (a frequently used abbreviation for New York City) in Wingdings was rendered as a skull and crossbones symbol, Star of David, and thumbs up gesture. This was often claimed to be an antisemitic message referencing New York's large Jewish community.[8] Microsoft strongly denied this was intentional, and insisted that the final arrangement of the glyphs in the font was largely random. (The character sequence "NYC" in the later-released Webdings font, in turn, was intentionally rendered as eye, heart, and city skyline, referring to the I Love New York logo.[9])

After September 11, 2001, an email was circulated claiming that entering "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 (✈︎🗏︎🗏︎ ☠︎✡︎).[8] This is a hoax; the flight numbers of the two airplanes that hit the towers were American Airlines Flight 11 and United Airlines Flight 175; the tail numbers were N334AA and N612UA.[10]