Chicago's Merchandise Mart: The Eight Creepy Heads Downtown

The Merchandise Mart was built by Marshall Field in 1930 and was later purchased by the Kennedy family. Joe Kennedy commissioned the "Merchandise Mart Hall of Fame" and eight creepy busts of great American retailers were created and placed outside this ginormous Art Deco building. It's SO ginormous that it once had its own zip code!
The heads are still there but are becoming twisted and decrepit, so thankfully they're facing the building rather than the Chicago River so they don't scare visitors on boat tours.