Greek and Latin permit some rather interesting word play. Here are two examples I like.

A Hellenistic Greek epigram (A.P. 10.43).

The first is a Greek inscription found on a sundial in the city of Herculaneum, which, like Pompeii, was buried by Vesuvius in AD 79. (It is much older than that, however, and was widely enough known and well enough respected to have found its way into the so-called Palatine Anthology.) I haven't tried to gimmick the accents, but I've manually written in 'h' for rough breathings.

hεξ hωραι μοχθοις hικανωταται⋅ hαι δε μετ' αυτας
γραμμασι δεικνυμεναι ΖΗΘΙ λεγουσι βροτοις.

Six hours are quite sufficient for work. But the ones after those,
reading ΖΗΘΙ with their letters say "enjoy life" to mankind.

To get the joke, you need to know

(1) that Greek letters double as numbers:
α = 1
β = 2
γ = 3
δ = 4
ε = 5
(digamma, no symbol available) = 6
ζ = Ζ = 7
η = Η = 8
θ = Θ = 9
ι = Ι = 10

(2) that there were 12 hours in the daytime, numbered 1-12, spanning dawn to dusk.

(3) that Ζ, Η, Θ, and Ι are the afternoon siesta hours 7-10 (i.e., 1:00-4:00, approximately).

(4) that ΖΗΘΙ is the Greek imperative meaning "live!," with a sense of "live well!"

So this poem engineers a neat little perceptual shift. It begins with the assertion that 6 hours are enough for work, and looks at first as though it merely goes on to designate the hours that follow by the letter equivalents of their numerical values. The words γραμμασι δεικνυμεναι "designated by their letters" prompt us to look at them just in that humdrum way. But once you get past the numbers, the word λεγουσι ("they speak/say") does all the work by making you now see that the numbers are "speaking" a word: the numbers not only designate the hours for enjoying life, they order you to!

Modern printing conventions (even the conventions that govern ancient Greek) give the game away pretty quickly thanks to formatting meant to facilitate the rapid and easy parsing of text. If you remember that all of these letters would have been in capitals and bereft of word spacing and punctuation in the original, you can see how the joke might sneak up on you and surprise you thoroughly.

On the Roman side.

MENTULACESSASVERPALUMBOSABSTULIT

This doggerel graffito is funny because it can be read two ways. Decoded this way:

Men tu lacessas? Ver palumbos abstulit.

it pointlessly says, "Are you harassing me? Spring has taken away the doves." The only redeeming feature of this is that it is functional Latin. It even reproduces a fairly common poetic meter.

But parsed this way:

Mentula cessas? Verpa lumbos abstulit.
Dick, are you giving up? Cock has stolen buttocks!

it naughtily partakes in the Greco-Roman tradition of imagining a contest for the affections of a penis: shall it be loyal to its female counterpart, or to the attractions of the buttocks? Abstulit may mean "steal" or "take away," but it can as well mean "win (as a prize)," which probably works better.

Bibliography.

Page, D.L. 1981. Further Greek Epigrams. (Page's poem 91 = A.P. 10.43.)
Courtney, E. 1995. Musa Lapidaria. A Selection of Latin Verse Inscriptions. (The Latin doggerel is Courtney's poem 98.)

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