Four-way Ambigrams
A four-way ambigram is a design that can be viewed in four ways (such as four 90° rotations) to see four different words or pictures. Four-way ambigrams are challenging for both designers and viewers. Making a readable four-way ambigram is more difficult than making a two-way ambigram because each shape must fit four constraints. As a result, four-way ambigrams are harder to read than regular two-way ambigrams. I created two passable four-way ambigrams (below). I link to a few good four-way ambigrams created by other designers (below).
Earth/Water/Air/Fire Four-way Ambigram

Earth/Water/Air/Fire four-way ambigram. Right side up, the figure says "earth" and the negative space says "air". Upside down, the figure says "water" and the negative space says "fire". I created this four-way ambigram in 1980. I had never seen a four-way ambigram — was this the first? I sent it to Martin Gardner, Scot Morris, Douglas Hofstadter, and Scott Kim. Gardner said it was splendid. Hofstadter said it was lovely, and that Scott [Kim] would like it.

Earth/Water/Air/Fire, tiled. This is a tiled version of my first Earth/Water/Air/Fire ambigram. It is more complicated because of the added tiling constraint. The design uses these symmetries: foreground/background (negative space), rotation (turn it upside down), tiling, and color change. It is not very pretty, but it is somewhat readable, and it is interesting.
North/South/East/West Four-way Ambigram

North/South/East/West four-way ambigram. Rotate the picture by quarter turns to see each of the words (as shown in the key below). In the starting orientation, north is up, south is down, east is right, and west is left. This design is rather pretty, and somewhat readable.

This design uses a very odd kind of symmetry, which I call Ferris-wheel symmetry. It contains only four letter shapes: 1=n/S/E/W, 2=o/a/e, 3=r/u/s, and 4=T. Each of the first three letter shapes appears at four different positions: north, south, east, and west, but the shapes are not rotated as you might expect. These shapes remain right-side up, like the seats on a Ferris wheel. The fourth shape, the "T", also appears at four different positions, but it is rotated. The "H" is made from two "T"s.
Four-way Ambigrams by Other Designers
Kevin Pease (Cerulean Stimuli) created a great four-way ambigram of the four elements, Earth/Water/Air/Fire. It is the best four-way ambigram I have ever seen. The glyphs are both readable and pretty. He made two versions. (I think version 1 is more readable than version 2.)

© Kevin Pease

© Kevin Pease
Kevin Pease also created a pretty four-way ambigram of the four seasons, Spring/Summer/Autumn/Winter. (I need to struggle a bit to read all the letters, but they are all there.)

© Kevin Pease
Please email me if you know of any other truly great four-way ambigrams.
Note that most four-word ambigrams are regular two-way ambigrams, not four-way ambigrams. For example, John Langdon created a lovely ambigram of the four elements, Earth/Air/Fire/Water, but it is a regular two-way ambigram.

© John Langdon