Readability is primary. From my point of view, if an ambigram is not readable, then it is not really an ambigram, it is an abstract ambiguous design.
After that, there are a few criteria that are all of approximately equal value:
Consistency of style
Integrity (recognizable presence and respectful treatment) of each letter
Attractiveness of the word as an entirety
General comment: it’s really great to see such a wide variety of structural solutions. This places much more emphasis on the thinking — the different minds that approached the problem, as opposed to a variety of stylistic variations on similar structures.
Vocabulary word: x-height — the height of the main body of lower case letters, exclusive of any ascending strokes (as found in d, h, k, t, etc.) or descending strokes (as found in g, j, p, q, etc.)
Mark Palmer, a.k.a. Wow Tattoos, USA: Without a doubt this is the most successful of the group, based on its clear and easy readability. Letter clarity is excellent. While the R would probably be seen as a B on its own, ambigram letters do not ever have to be seen on their own, and if we notice that the R is more like a B at all, it will be long after we have read the word as a whole. The context of a recognizable word benefits a dubious letter. No doubt, the dramatic flourishes distract us from the strangeness of the R as well. The flourishes might be thought of as meaningless decoration, they do in fact play that important functional role.
I do think that there is a bit of stylistic conflict between those flourishes and the racecar-like intensity of the italic angle. While the flourishes would hint at elegance, the design as a whole has a harshness and slightly ungraceful feeling about it.
Beyond the clear success of Wow Tattoos’ entry, it will be hard to rank order the rest, and I think it best that I not try. I will simply describe the pros and cons as I see them.
Scalpod, USA: Readability is quickly overwhelmed by concept here. Although I love the idea of the arrowheads dotting the i’s, that’s an incredibly subtle detail by comparison to the large, dramatic, circular arrows at each end. It’s hard to find and recognize the S, and without a strong starting point, an ambigram is at a great disadvantage. While the U/L solution is clever, it too is a bit exotic and unfamiliar, and with the big arrows pointing right to those letters, when we can’t be sure of their meaning either, I think the reader will be likely to give up. On the plus side, I’m very fond of the form of the G/A.
Homero, Chile: I love the straightforward simplicity of this solution. It looks casual and spontaneous, but behind that relaxed attitude are letter structures that are so intelligently crafted that they do not require any dramatic treatment in order to succeed. However, a couple of strategic lapses in judgment hurt the success of this design. They take place in the connections of the letters NGULAR. Easiest to fix are the connections of the U to the G and L. I see no need for them to touch, and I think that the unnecessary connection of the GU weakens the necessary connection at the top of the G. The NG connector is quite necessary as it plays a more important role finishing the A and beginning g the R, but it’s much too strong. In both locations, it can be a much lighter stroke, and as such will enhance the word as a whole.
Rickxard, Austria: I don’t know, of course, but I suspect that the designer created a mirror-image ambigram to complement the graphic rendering of the black hole. I find that mirror image ambigrams are far more difficult to do well than rotational inversions. And unfortunately, some words cooperate with our attempts to make ambigrams, and some don’t. I think that the N, G, A, and T are so severely compromised that we can’t call this a successful ambigram.
One significant drawback to this piece is the background. It unifies the design, of course, but the dark value diminishes the accessibility of the letters. Its pattern seems unrelated conceptually and graphically, so I don’t see the need for it.
The clever letter-by-letter solutions are successful and enjoyable. More even letter-spacing will enhance this ambigram; I would especially appreciate more space between the A and R in the horizontal reading (N and G of the vertical reading).
I think it was a strategic error to complete the square of this quarter-turn. Readers of the Roman alphabet start looking for recognizable letters and words in the upper left, and we are unsuccessful in the attempt. The ambigram will be far more successful as a two-part right angle.
Burkard Polster, Australia: Of the solutions that involve a conscious effort to include the concept of a singularity (popularly known as a ‘black hole’), this one is the most thoroughly and successfully integrated. This one is the only chain ambigram in the group, which means that the letter-to-letter translations are unique among the entries. With the exception of the S/A, they are remarkably successful, and in another word and setting the S/A would probably work just fine. But the chain places an extra burden on the initial letter, calling for it to stand out and say, ‘Hey this is where the words starts!’ If the word were GULARITYSIN it would work better, as the G demonstrates what the initial letter needs to do.
Here again, I think that the artistic treatment — the diminishing concentric rings, and especially the double ring that contains the entirety — detract from the success of the ambigram. We have a strong concept and a strong letter-to-letter translation, but a word that is hard to read.
Derren, England: Stylistically and aesthetically, I think this is a very enjoyable ambigram. Oddly enough, though, despite a high degree of letter-by-letter readability, I think the readability of the word may be a little lower than ideal. It’s so hard to find any real problem areas, that I think it may be the glow around the letters that diminishes the easy reading of the word. The letter-spacing is not by any means too tight, but having the glow fill up those spaces to the degree that it does seems to cause some congestion. One possible, but surprising, problem: the G is so much more conventional in its form and style that we read it more quickly than the other, more exotic, letters — even when it’s upside down being an R.
Roopaksuri, India: This version of SINGULARITY is probably the most successful in terms of developing a successful, very appealing, and credible style — it could easily be the basis for a new font design. But the letters that make up ambigrams don’t need that kind of consistency, as they will only appear in one given relationship with other letters. The consistency of this style is, ironically, the weakness of this ambigram. The consistently flat-sided letter style, eliminates some of the differences among letters that help them be read. The consistent weight of the bold vertical strokes adds to that effect, and the very consistent letter-spacing (normally an important benefit) creates too regular a pattern. One significant decision that also helps diminish readability is the burying of the dot of the I within the x-height of the letters. The comparatively wide proportion and the italic angle create a highly streamlined experience, causing the eye to shoot through the word without enough letter recognition. The dot on the i would be a worthwhile speed bump to aid readability. Again, the letter-to-letter translation is quite good here. The RI connection works surprisingly well, as the heavy weight minimizes the noticeability of that unnecessary and potentially disruptive stroke. The structures of the S/Y and G/A are particularly appealing.
Syfi, USA: The calligraphic forms that make up this version of SINGULARITY are absolutely beautiful on their own, and might make a successful ambigram, but the downfall here is the letter-spacing. Odd, and potentially problematic as the ascending G is, I think it might be made to work — at least I think it’s much less of a problem than the uneven letter-spacing.The inherent space within the U and A forms, and the necessary space between the R and I and the I and T (and even to a small degree the T and Y) are fine, but the GULAR are so tight that they create a scramble of strokes more than a series of recognizable letters. I like very much the way the dot on the first I creates a tail for the Y, and in my opinion, the S was not required to do the same job. That means that a successful chain ambigram would have been possible with the S as the link. In addition, here too, the dot on the first I would be more effective if it were higher than the x-height, and it would enhance the Y-tail as well. I don’t understand the relevance of the wings, and while they are beautifully rendered and integrated with the S, they create a very busy focal point that, by attracting attention, may further diminish readability. Nagfa, Singapore: All attempts at ambigrams are challenging, but perhaps the greatest self-imposed challenge in this competition is this surprisingly successful attempt to create the word using a single glyph. I must admit that, obvious as it may be, I missed that this is an example of a “spinonym”. I had to ask. Unlike a “regular” ambigram where the word can be read from more than one point of view, here a single character can be read from multiple viewpoints as it spins along the length of the word. One of my most highly regarded logo designs could be called a spinonym. It’s for a printer named DUCA. You can probably visualize the design already. So it seems to be an extraordinary achievement to create a single shape that will spell out a word as long as SINGULARITY. Holding this ambigram to the same standards as the others seems somehow inappropriate, as the challenge is so different, but if I did, I would have to say that the readability is rather difficult, given that the word might appear to begin with 5IA, and the Y is certainly the greatest victim of the approach. The GULA read very easily. It’s hard to say which letter is the most ingenious, when it’s the single shape that deserves that title, but I keep coming back to the R as the most remarkable success.
Conclusion: I chose this word as a challenge because I knew that it was “do-able” but difficult. The fact that several different kinds of ambigrams emerged seems to bear out that idea. One of the critical decisions involved in any ambigram is, ‘what happens in the middle.” In general, it’s best if there can be one letter in the middle that will invert or reflect easily. Two of the more successful designs involve an invertible L.
One of the tricky parts of this word as an ambigram is that it’s full of temptingly easy letter-to-letter translations but, with the exception of Wow Tattoos’ solution, some amount of combining letter parts to create other whole letters was necessary. How this sleight of hand was achieved often influenced the success of the ambigram.