I don’t even like it that much (I wanted to fast forward anything that didn’t contain Meryl Streep), but I think The Deer Hunter fits the bill. Understanding the Vietnam War (and its effect on the common people) is a big part of the American psyche.
Actually, I think what would be important to know would be the age of the individual.
I’m 40 so this is my example.
The seventies, start with what kids would have seen then. Star Wars. Superman (I’m thinking the 1970’s with Christopher Reeves).
Movies from the teen age time period… the 80’s stuff… Big Chill, Kramer vs Kramer for social commentary. Breakfast Club, Back to the Future, Ferris Bueller, for the teen stuff, also the Vietnam and serious stuff … Deerhunter or Platoon.
Movies from the 90’s Forrest Gump, American Beauty, Pulp Fiction. Titanic, I guess, its referenced everywhere, but I could live without seeing it agian.
Important Movies from the past decade. I guess I have too much historian in me to decide what those are exactly. Matrix. Erin Brokovitch.
Then go back and fill in classics from before his age. Not everyone his age will have seen John Wayne movies, or Gone with the Wind, but it will help fill in historical gaps, and a certain amount of cultural literacy.
This is an example for a 40 year old. Different ages will have earlier /later fill in gaps, iconic teen movies and so forth.
Deliverance
Network
The Grapes of Wrath
Annie Hall/Manhattan/Hannah and her Sisters/Sleeper/Manhattan Murder Mystery (gotta have some Woody Allen in there)
Maybe an Irwin Allen disaster flick: Poseidon Adventure, Earthquake, Towering Inferno
Some John Waters, perhaps: Polyester, Hairspray