High Street and Cumming Street. High Street has two high schools on it so naturally...
Cumming Street is in a poor neighbourhood; last year at a Halloween party I saw a girl dressed up as a prostitute, with a fake street sign for Simpson and Cumming strapped to her back; the area has a bad reputation. It's just a few blocks away from me! I've asked the city to rename one of the cross streets to Seaman but to no avail.
Down the street from me is a street called Wiley. Unfortunately, Coyote Street already exists in the city, so we can't get that name combination.
John Street Road has been stolen a few times as well because it's a very unusual name. A friend of mine when I was a kid had a John Street Road sign in his rec room.
Not sign related, but the postal code for the village of Murillo, just west of Thunder Bay, is P0T 2G0 - Pot 2 go.