Urbandictionary.com defines the term to mean alcohol illegally made, sold, or transported. Several sources describe that the term originated with cowboys concealing a bottle of liquor in their tall boots. There was a show titled “Whiskey” on the History channel that had an example of a different method of “bootlegging” alcohol in the Prohibition era. Bottles were made with a rounded back, which allowed then to be strapped onto women’s legs and concealed under their long and billowing dresses.