Richard Edes Harrison was a trained architect, artist and mapmaker whose maps in the years leading up to and through WWII gave Americans a new perspective on the world. World War II Led to a Revolution in Cartography. These Amazing Maps Are Its Legacy [more inside]
Jonathan Roberts is a fantasy mapmaker, who produced the maps for the official Game of Thrones atlas. He talks about mapmaking to Wired here. He also has a website with lots of nifty maps, as well as tips on making your own.
By the creator of the California Rail Map, and inspired by ideas from various agencies and advocacy groups: A Map of the US High Speed Rail System