Long Strange Trip, or the Writer, the Naked Girl, and the Guy with a Hole in His Head (1999)

As magazine writer Phil Austin arrives for work in the morning he is struggling to deal with the end of his relationship with his Editor Andrea, the end of his weekly column, and the cancellation of his book contract. Humbled, he reluctantly takes on an interview assignment, and heads for a stip club to interview stripper Becca. She is looking for an escape from her present life, and Phil, feeling he has little to lose at the moment, agrees to drive her north into the sticks, to her Father's Survivalist Compound, knowing little of what he is getting himself into, nor how far or where he is going. Once Becca's brother Lars joins up, the road trip becomes a slow humorous descent into absurdity. Amusingly borrowing plot from "Apocalypse Now," (the film is officially and "homage"), the Canadian border reflects "Apocalypse"'s crossing into Cambodia," and the dad provides a twisted version of nod to Brando's Kurtz. All the while, the story manages to balance it's humor with a subtle progression toward a true understanding of Becca's character, succeeding in under-mining any preconceived judgments we may have had about her being a "Stripper." In the end, we - and the character Phil - fall in love with her and respect her.