Unless my early schooling memories deceive me, this question sneaks in just before the 20 year cut-off (but apologies if not). But an offhand comment just made me wonder why on earth a font like Wingdings became such a longstanding part of word processing software. Why was it even invented in the first place? Why did it stick around?
You can think of wingdings as the predecessor to emoji. It was introduced by Microsoft in Windows 3.1 as a way to be able to include symbols in their word processor. Most of them are commonly understood symbols gleaned from icons they licensed.
This gave you a scalable way to include a stop sign in a project without having to generate a picture yourself and copy it in. It stuck around because it is much easier for a word processor to properly display and print a resized font character than clip art or putting a JPEG in.
While wingdings weren't a standard part of the Unicode standard at their release, they became part of the standard in 2014(needs verification) and will be with us now until they decide we don't want it anymore.