Part 5: Show Them Those Iconic Images

Regardless, whether they have seen the movie or not, there are probably very few people who don't recognize that iconic image of Audrey Hepburn holding that long cigarette.
Due to that recognition, a movie, such as Breakfast at Tiffany's, is a perfect entrance into classic movies. From there, you can take on some of Hepburn's other work, like Sabrina or Love in the Afternoon. You could even go the road (much) less traveled and check out a flick with George Peppard, such as How the West Was Won.
There are many movies like this that boast iconic images that would be worth checking out, such as James Dean in Rebel Without a Cause, Humphrey Bogart telling Ingrid Bergman to get on the plane at the end of Casablanca or Cary Grant being chased by a plane in North By Northwest.