Years ago I came across the website of avid ephemera collector Richard D. Sheaff. Amongst the many eccentric examples of 19th century artistic printing and lettering one category stood out for its visual and conceptual ingenuity. Filed under “Anamorphic Writing”, Sheaff gathered samples of graphic riddles intriguing for their puzzling complexity.

A message hiding in plain sight, revealed only when tilted at an extreme angle and looked at with one eye closed. This hyper-stretched lettering style is intended not to elucidate but to obfuscate. The deciphering of the message calls for interaction with the medium, for an active engagement rather than a passive consumption.

Exactly when this effect was first employed in the lettering arts is hard to pinpointed. Knowledge of perspective distortion was applied to letterforms as early as ancient Rome. A prominent example is the iconic inscription at the base of the Trajan column showing significant difference in size between lines of text in order to compensate for the viewer’s low position underneath the plaque. In his «Vnderweysung der Messung…» from MDXXV, Albrecht Dürer explicitly illustrates this practice amongst other geometric applications in the construction of letterforms.

The Renaissance, with its fusion of science and art, its fascination for perceptional phenomenon, optical devices and geometric laws was crucial in the conceptualization of central perspective; the analysis of visual distortion from a subjective point-of-view.

Leonardo da Vinci (of course) is often claimed to be the first artist to indulge in deliberate deformation in this sketch from 1515. Yet, it was the 1530s and the transition from the ideals of the High Renaissance to what was latter coined Mannerism that can be declared the heydays of artistic anamorphosis.

The most prominent example might be Hans Holbein the Younger’s masterpiece «The Ambassadors» from 1533. Depicting two nobleman with their physical and metaphorical possessions, the painting also sports a diagonally anamorphized human skull stretched over the lower quarter of the image.

Lesser known yet equally fascinating is the work of Erhard Schön, a disciple of Albrecht Dürer. His «Vexierbilder» are a series of woodcut riddles to be deciphered only by the curiously inclined. As an extension of his mastery of geometry and perspective, Schön might be the first one to drastically distort letterforms in his work.

Besides their technical dexterity, these two examples also show the subversive potential of anamorphic disguise. By superimposing two images, a deeper psychological meaning or social commentary can be implied. In Holbein, the skull acts as a reminder of the mortality of the arrogantly wealthy; in Schön, a critique of the socio-economic system of catholic feudalism or sexually explicit imagery are profoundly embedded.

In the course of letterform history, anamorphosis remains a visual curiosities used for various reasons and effects. Examples range from the camouflaged lyrics of a patriotic song issued during the Nazi occupation of Norway to the outrageous signature of Bavarian comedian Karl Valentin. As this manual from 1903 shows, perspectively distorted letterforms might have been a common, yet not very common request from sign painters and lettering artists.

The eponymous Anamorphe typeface introduces this odd practice and the ability for cryptic obfuscation into the realm of digital typography. Variable font technology enables fine tuning of horizontal width and vertical weight to fit the to-be-disguised message at hand.

As shown in many of the historical samples, the effect is at its best when two or more words or phrases overlap in a grid like manner, to be read at an angle from their respective direction.

Anamorphe cites a manifold of the encountered examples resulting in an amalgamation of conflicting desires. Angular details reside comfortably next to round features. What starts out as sans in the most condensed style successively grows serifs in order to maintain a picket-fence effect. The ball terminals found in some of the historical specimens are implemented as stylistic variants, adding an absurd, ornamental twist to the already puzzling mix.

Not yet.