"Ironic Serif: A Brief History of Typographic Snark and the Failed Crusade for an Irony Mark" by Maria Popova (Brain Pickings)
As it happens, Popova wrote another piece on punctuation concerning an author who commands a great deal of my attention:
Theodor Adorno on the Art of Punctuation by Maria Popova (Brain Pickings)
Adorno took punctuation very seriously, as evidenced by an essay I have not seen: “Punctuation Marks.”
A translation of it by Shierry Weber Nicholsen was first published in the Summer 1990 issue of the poetry journal The Antioch Review and later included in Jennifer DeVere Brody’s altogether excellent Punctuation: Art, Politics, and Play (public library), the essay explores the “definitive physiognomic status” of each punctuation mark, its uses and abuses in the hands of writers, and how punctuation helps shed light on the relationship between language and music which, as we know, worked in tandem to help humanity evolve.
Popova proceeds to detail Adorno's views. Note that Adorno vehemently objected to punctuating ironic remarks. (Note also that she links to her article on the ironic serif.)
Note that Adorno's essay is discussed in Brody’s Punctuation: Art, Politics, and Play, but it is not reprinted there. Adorno's essay was collected in book form here:
Adorno, Theodor W. “Punctuation Marks,” in Notes to Literature; Volume One, edited by Rolf Tiedemann, translated by Shierry Weber Nicholsen (New York: Columbia University Press, 1991), pp. 91-97.