As a Milwaukeean, I can confirm that the high point of Milwaukee's cultural relevance... was used as somebody's garage (or whatever) in Transformers 3. Appropriate.
I still remember one thing about Bridesmaids - that Hollywood thought a federal interstate between Chicago and Milwaukee was a two lane country road.
That said, you can tell neither of them lived in Milwaukee prior to their college years - the infamous Freeway Ramp to Nowhere used in The Blues Brothers was up and barricaded off for years, as another freeway project it would have connected to was cancelled, before eventually being torn down.
(When I do introduce myself to others on calls, especially with foreign-borns, I literally do say "I'm from Milwaukee, 90 minutes north of Chicago.")