@rascal - To be fair, Beerfest is just a goofy comedy centered around a beer drinking contest. It's good fun.
A quick google search turned up a short (and possibly apocryphal) history of beer boots. I'll summarize:
First used by the English in the 1800's, fashioned after riding boots and used at hunting lodges.
Then they caught on in Germany, where they were part of initiation rites in the military (drinking beer from a boot). This evolved into giving beer glasses shaped like boots as mementos and as awards.
They made their way to the US via soldiers returning from service in Europe, and became really popular after the release of the movie Beerfest in 2006.