21. The Graduate (1967)
Director: Mike Nichols
Stars: Anne Bancroft, Dustin Hoffman, Katharine Ross, William Daniels, Murray Hamilton, Elizabeth Wilson
Vacation destination: Mrs. Robinson's house
Ben (Hoffman) has just graduated college and he finds himself in what might be his last summer vacation, the bittersweet hiatus after college and before entering the real world, or, if you'd like to further procrastinate, grad school.
Ben is on the fence about what he'll do with himself after summer ends, but he's not on the fence about what he'll do with Mrs. Robinson. He gives in to the older seductress, but the plot considerably thickens when he realizes he's fallen in love with her daughter.
Hoffman's expertly acted predicament yielded a slew of Oscar nominations, including a win for best director, and is widely recognized as one of the greatest films ever made. Here's to you, Mrs. Robinson!