I would assume that by "bootlegging era" you're referring to the period of the US Constitutional prohibition?

It must be noted that "bootlegging" was still an active "profession" in Kansas in the late 1950s and perhaps a little later, due to local/state prohibitions, and remains at least an "informal pastime" now due to differences in taxation by state and local jurisdictions.

As is the case with "Folk Traditions" in general, bootlegging (sort of) still lives.

John