If only these were actually easy to stick into emails, I'd be way more likely to use emoticons on a regular basis. :(
There's something truly terrifying about a mom who has just learned the arcane secrets of making funny animated faces on the Internet. They should make a horror movie about this. [Update: You can find Genna on her Tumblr! You should follow her. Genna - your mom is awesome.]
From the magazine Puck, published in 1881. Someone was way ahead of their time - though the boring description full of long unpronouncable words shows just how far removed they were from the modern (i.e. better) way of doing things. Lulz.
The = sign makes a serviceable Hitler mustache - which is all you need to know to begin offending your friends over instant message. Here's a list of historically accurate options to get started with.
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