One of my goals (besides finding the earliest and latest stamps I can, and I may have peaked too early on the former) is to find a stamp from as many different decades as possible. So here is an otherwise not particularly distinguished one I saw on my walk today to represent the 1950s.

Another one from the Department of Public Works, 195…7? 2? I initially thought 7, but it looks too rounded. On the other hand, there’s definitely no bottom bar to make it a 2. It’s on the east side of Shepard between Kalamazoo and Stanley Ct. (a curiously tiny, glorified alley between Shepard and Leslie).

Update 2/27/21: Based on seeing several others like this, I am now sure it’s 1952.