14. The Graduate (1967)
Recent college grad Benjamin Braddock (Dustin Hoffman) has gotten himself into a bit of a pickle. After revving up the engines on an illicit affair with Mrs. Robinson (Anne Bancroft), the very married wife of his dad's business partner, he is encouraged to go on a date with Elaine (Katharine Ross), Mrs. Robinson's beautiful, more-age-appropriate daughter.
Though Benjamin finds himself falling for the younger Robinson, he's promised her mom that he'll be on his worst behavior. Which in this case includes alternating between ignoring and insulting Elaine, and then capping off the evening with front row seats at a strip club. Good times!