January 17 celebrates the American history of bootlegging. For those of you aren't familiar with bootlegging, it refers to illegal trafficking of goods, usually liquor. The term "bootlegging" dates back to the late 19th century, when traders would tuck flasks of liquor into the tops of their boots.
So why is National Bootleggers Day on January 17? Because on that day in 1920 Prohibition went into effect and the United States legally became dry. Of course, the reality was far different. With a large market demand for alcohol Prohibition spawned the rise of bootleggers such as Al Capone. I may have engaged in some small scale bootlegging myself, as a few years ago I may or may not have brought a few bottles of Cuban rum home (it's legal now).
I prefer to celebrate National Bootleggers Day with a Scofflaw, as a bootlegger is a type of scofflaw. And I love the cocktail. Although both words were popular American slang terms for lawbreakers, bootlegger was part of the common vernacular well before Prohibition.
Whether you're into history (like me) or not (like many other people), have a drink and celebrate! Just don't tell the authorities from where your booze came.