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Why the Wingdings font exists Share this story It seems as bizarre as it is ubiquitous. What is Wingdings thinking? Why would someone want to write a comma using a mailbox? Why would anyone think we want to compose in peace signs and crosses and heart shapes? The below is just a brief example of Wingdings weirdness: Wingdings and friends. (Vox) But Wingdings is much more than just a quirky font. It was and remains a phenomenon. In the early 90s, it was one of the first times people realized fonts could break through to the mainstream. One of the creators of Wingdings, Charles Bigelow, of the legendary design studio Bigelow & Holmes, told me Wingdings marked one of the first times a font became part of the popular culture. ....