Bruce Roberts, Inc - A Map of Chicago’s Gangland (1931)

Apparently, “Designed to inculcate the most important principles of piety and virtue in young persons, and graphically portray the evils and sin of large cities.”

Not the sort of aesthetic you’d expect from a gang territory map. How weird and/or cool is it that the  north arrow is a handgun?

Hans Werner - University of Wisconsin Visitor’s Map (1937)

A very amusing cartographic product lurking in my alma mater’s archives. The marginalia is packed with everything from indigenous-inspired patterns to architectural renderings to straight-up inside jokes: even my best Googling can’t determine if “Prof. Benny Snow” is an actual person.

My favorite inexplicable bit is the giant pigs by the swine barn: no other building on campus gets this same sort of pictoral treatment.

Stanley Smith - Great Britain (1956)

Note that the more accurate title would be ‘British Isles’, since this map focuses on Ireland, too. This region seems to be a magnet for maps in that attractive midcentury  letterpress style: see this one for another favorite example.

Antonio Petruccelli - Oahu is Hawaii (1940)

There’s a lot of things I love about this map.

1. Oahu IS Hawaii, because it has forts and beaches. Those other islands are ‘cattle country’ and ‘a leper colony’, and can therefore be comfortably disregarded.

2. Look at the feathery way those mountains are drawn! They’re quite pretty.

3. The matter-of-fact, casual treatment of Hawaii as being a resource for only two things: crops and military bases (notice the helpful labeling of ‘sugar cane’, ‘pineapple’, ‘golf club’, and ‘big guns’)

4. The “hindsight is 20/20” moment you get by reading the map talk up Pearl Harbor. The base is, evidently, well protected by attack… from sea.

“The United States of Dixie” - Confederate Air Corps, 1961

Tongue-in-cheek midcentury mapmaking.