I have a few.
"SLOW CHILDREN PLAYING" My brother stole one of these (he went through a roadsign larceny period, he had "no dumping" over his toilet) and said that he was writing a letter to the governor about how mean it was to point out that the children were slow. Commas would help, people!
"Pick a Flick" video store. The problem? The "L" was way too close to the I, and it was in all caps. It looked like you were picking something else.....
"Caution, Blinding Sun" on the side of the road near our bridge. Umm....ooooookay.
Braille on drivethru ATM's.
"Need to Learn to Read? Let **** Adult Literacy Center Help!" How are they going to read the ad?