This could be a very brief post, because there is no essential Stephen Leacock.
Unless, of course, we take his “Unsolved Riddles” trope as somehow capturing it, which is in effect what we are doing for his Sesquicentennial, at least until someone comes up with a better idea. We embrace both the singularity and the plurality of the man.
In how many ways was he plural? Let us count them.
His parents must have been believers in pluralism, because they had eleven children, of which Stephen was the third.
He was raised in plural environments, first as a village lad in England, then as a farm boy in Georgina Township, Ontario, then as a schoolboy in Toronto at Upper Canada College. From there he went on to study at the University of Toronto, to teach briefly in Uxbridge and much longer at UCC, then on to the University of Chicago and a Ph.D. in Political Economy, which was not a plural discipline in his day but probably is now.
He then taught for the rest of his working life at McGill University in Montreal, but overcame the singularity of that by teaching and writing academically in both Economics and Political Science, and by creating for himself three other careers as a writer of humour, a public speaker, and a public intellectual concerned with all kinds of things with no regard for academic boundaries. His innate pluralism shines through in his writing and speaking perhaps more than in any other aspect of his life.
He wrote 53 books and some 1,500 “pieces” (many of the latter appearing also in books) and gave some 750 speeches that we know about.
He had one wife, one son, and in later years after his wife died, one special female friend. He had many male friends, although it appears only one especially close one.
He felt some sense of belonging in three countries — Canada, England, and the United States — although not completely in any one of them. He felt a strong loyalty to one empire, which he excoriated on every possible occasion for being less than it could and should be.
I think it is fair to say that he had four homes, three in Montreal (his house, McGill, and the University Club), one near Orillia. The nature of his relationship to Orillia has caused such a plethora of interpretations as to be almost a pluralism in its own right.
His reading was pluralistic to extremes.
He was a liberal social democrat in political ideology, attached to the Conservative party. In Canada this is not as pluralistic as it sounds.
He drank copiously, but whether of blended or single-malt scotch is unknown. Probably he drank whatever was available, which is a pluralistic approach.
He is widely known nowadays for the creation of one place — Mariposa — which has however been characterized (by Ed Jewinski) as a locus of “fragmentation, incompleteness and inconclusiveness”, which is a pluralistic way to be. He himself said that Mariposa is “about seventy or eighty” “real towns”, which is very plural indeed. It has been subject to plural interpretations, of which only one is correct: mine.
The degree of pluralism manifested in Stephen Leacock himself remains, therefore, yet another Unsolved Riddle.