Always on the search for those ever-elusive "so bad it's great" films. 

What began in 1998's The Waterboy by Adam Sander becomes fully realized in 2000's Little Nicky. Witness the birth of modern-era Sandler. The road to Hell is paved with Little Nicky DVDs.
"There are several sexual characteristics to Bigfoot that I wanted to make sure came out, since it’s very integral to the story." - Actual quote from the director.
Based on how much he smokes in this film, I'm pretty sure the production paid Dan Haggerty with cartons of cigarettes.
Half of this film's budget was spent on belts, denim, and various chains of varying length.