This [1] series of essays explores the differences between Google Maps and Apple Maps. Despite the essays' shortcomings (author is actually working for Apple Maps, poor choice of figures and diagrams, no discussion of underlying data at all), they still offer an interesting comparison of how the two main providers of proprietary map services represent our world.
[1] http://www.justinobeirne.com/essay/cartography-comparison
According to the Good design Awards,
the autograph map depicted in this entry is one of the best designed objects of 2016.
This map was created by Hajime Narukawa who worked on this for over 15 years. More info here.
This article in Slate [1] is already four years old and may be old news to some. But it nicely highlights some of the challenges of cartography (label placement, choice of features, ...), and tells the story of an impressive feat done by an independent cartographer: Producing a paper map of the United States on his own, over the course of two years. It's a story of skill and dedication, worth a read for those interested in cartography.
