Before starting Larry Gets Lost in Chicago, based purely on my memories of Chicago from the 80s, my first thought was to use the Chicago Picasso for the cover. But it didn’t work for a couple of reasons. First, in order to avoid putting the sculpture’s face behind the logotype it had to be shrunk too much. Second, after visiting Chicago and researching the book, it seemed like the Picasso just wasn’t that big an icon of Chicago anymore. (Things change a lot in 25 years!)
Then I played with the idea of using the marquee of the Chicago Theater, and actually making the marquee part of the title.
They used the marquee (sort of) for the logotype of the movie CHICAGO.
The real icon of Chicago now, their Space Needle, is the Bean. But the Bean caused it’s own problems. It’s huge and horizontal, so it just wasn’t working.
After messing around with the marquee idea some more, I started to like it. The dark red marquee was just an accident I noticed when moving objects around in Illustrator but it works for some reason, even though it’s illogical. It helps make the white logotype pop. (The color palette’s still a bit too firey.)