Donald Knuth – The Patron Saint of Yak Shaves (2017)
Granted, there is a substantial degree to which font design has a strong subjective element (even though there are some non-subjective metrics that must be met too). However, the font that emerged in "Yak shave #4", Computer Modern, manages (for me) to pull off a somewhat exceptional double feat. On the one hand, it is to my eyes one of the ugliest fonts designed during the 20th century; on the other, my experience of it as a reader (hence again, my eyes) is that it is one of the easiest to read fonts ever created. I assume that DK found CM to be both beautiful and readable, which is fine, but I think it's even more remarkable that he could have created a font that someone with a modicum of interest in font design and typesetting could find both ugly and very readable.