American Depravity (2009)

Kenny is a young man struggling to make ends meet in New York City. He is roommates with a fifty-year-old stockbroker named Mr. Sampson. Contrary to his age, Mr. Sampson is a pervert who consistently fails to understand the bounds of socially acceptable behavior. When Kenny's girlfriend inexplicably dumps him, Kenny mistakenly seeks the advice of Mr. Sampson to try to win her back. And, of course, depravity ensues.