I was looking around for something else, but I found an old article about Diogenes the Cynic, so here is a small part of it that you might enjoy, some of his great replies and, most importantly, linguistic puns, of which he was famous of.
Pun no.1
Legend has it that Alexander the Great visited Diogenes when he was lying in the market, basking in the sun outside of his ceramical pot he used as a dwelling. When Alexander asked of Diogenes if he could do anything for him, Diogenes replied with the simple reply “ΑΠΟΣΚΟΤΗΣΟΝ ΜΕ” which in that context meant “You are blocking the sun”, but even today when someone is annoying and we want to get rid of him the phrase “stop bothering me” is “μη με σκοτίζεις” which means “stop darkening me (my day)” … imagine saying that to the most powerful man in your country. Alexander himself was said to have been impressed by the response.
Pun no.2
Upon learning that a particular doctor, who was a known womanizer, was called to heal the eye ( eye = οφθαλμός, pupil = κόρη ) of a young unmarried girl ( unmarried daughter = κόρη ), Diogenes commented “ΟΡΑ ΜΗ ΤΟΝ ΟΦΘΑΛΜΟΝ ΘΕΡΑΠΕΥΩΝ, ΤΗΝ ΚΟΡΗΝ ΦΘΕΙΡΗΣ” which translates to “beware whether you damage the κόρη, while trying to heal the eye”, playing on the double meaning of the word “κόρη”, as well as the double meaning of “φθείρω” which can mean physical and ethical damage.
Pun no.3
Once Diogenes saw a very bad drawing of two centaurs and he wondered “ΠΟΤΕΡΟΣ ΤΟΥΤΩΝ ΧΕΙΡΩΝ ΕΣΤΙ” which means “which one of them is drawn the worst?”, but “ΧΕΙΡΩΝ” does not only mean “worse”, but was also the name of the mythical centaur and mentor of Hercules, Χείρων (Chiron). So, his words could have also means “which one of them is Chiron?”
Good reply no.1
When asked which animal is the most dangerous, Diogenes replied “ΕΚ ΤΩΝ ΗΜΕΡΩΝ ΟΙ ΚΟΛΑΚΕΣ ΕΚ ΤΩΝ ΑΓΡΙΩΝ ΟΙ ΣΥΚΟΦΑΝΤΑ” which means “out of the tame ones, the flatterers. Of the wild ones, the sycophant.”
Good reply no.2
Once, at a musical performance, the guitar player was a person that was huge and muscular, but was horrible at playing the guitar. After the song was done, the viewers booed and jeered, but only Diogenes was heartily clapping. When he was asked why he was applauding such a horrible performance Diogenes replied “ΔΙΟΤΙ ΤΗΛΙΚΟΥΤΟΣ ΩΝ ΚΙΘΑΡΩΔΕΙ ΚΑΙ ΟΥ ΛΗΣΤΕΥΕΙ!” which means “because that man chose to play the guitar, instead of becoming a highwayman/brigand”
Good reply no.3
When a bald man cursed/swore at Diogenes in the market, Diogenes replied: "ΕΓΩ ΟΥ ΛΟΙΔΟΡΩ ΑΛΛΑ ΤΑΣ ΤΡΙΧΑΣ ΕΠΑΙΝΩ, ΟΤΙ ΚΡΑΝΙΟΥ ΚΑΚΟΥ ΑΠΗΛΛΑΓΗΣΑΝ” which translates “I will not swear at you, but instead I will praise your hair that decided to do away with such an ill-tempered skull”
