Here is the best example of gerrymandering you will ever see. If you're not familiar with the term, it's one of the ridiculous techniques politicians use to gain an advantage in the two-party system. The green region is a single congressional district in Illinois, commonly called "The Earmuffs." Using the scale on the map, the thinnest sections are about 200 feet across. Why divide a region into rectangles when you can have earmuffs instead?

Image from this Wikipedia article. More info in this Washington Post article.