5 times for and?
Would the sentence, "I put dashes between Fish and And and And and Chips in my Fish And Chips sign" be clearer if I put commas between Fish and and, and and and And, and And and and, and and and Chips?
As for is, it is kind of cheating, but, "Is is is?" is "Is is is?"
However the real record holder is buffalo. Buffalo can mean the city, the animal, or "to bewilder and confuse". Between those three meanings you can always find a correct gramatical parse for the word Buffalo, repeated any number of times. For instance, Buffalo buffalo buffalo buffalo buffalo Buffalo buffalo! means "Buffalo buffalo bewilder and confuse buffalo that bewilder and confuse Buffalo buffalo."