The Swimmer (1968)

Woefully underrated movie starring the endlessly charismatic Burt Lancaster as Ned, a man who decides to swim home one summer day through all his neighbor's pools in the upper middle class suburbs of Connecticut. If you're slightly confused but intrigued, you'll love it. It's a perfect entry into the midcentury white suburban malaise sub-genre that I personally love, based on a very good short story by John Cheever that first appeared in the New Yorker in 1964.