I have a vague recollection of my first exposure to ambigrams. It was a small article in Discover magazine. There was some write-up about some fellow who had invented a particular font so that the letters could be read upside-down (possible as the same, or maybe a different letter formed). Supposedly he was inspired by seeing letters writen on the sides of rotating automobile tires, I think?
Anyway, the article showed how the word "NEWSMAN", if written in the font read the same way when rotated 180 degrees. This was pretty cool to me, and I kept a lookout for other words that had the same trait ("NOON", "dollop", etc...)
I never really experimented with my own fonts, though. Ambigrams were not something I doodled with very much.
In fact, it wasn't until late 2004 that I really renewed my interest in them (as a Christmas gift for my mother I purchased the book Inversions by Scott Kim -- a true master at ambiguous writing).
In late February of the following year I started trying my hand at my own ambigrams. Mainly this served as a way to kill time on cross-country airplane flights. Mostly I started doodling with names of my friends. Below are some examples (all of them are 180° rotational unless otherwise noted).
I will add more as I create them (and probably refine some of the above).
- Eric Harshbarger