A few days ago I was flabbergasted when I discovered that my new rommate hasn't seen almost any movie released before the 60s (except Casablanca and Citizen Kane). The thing is that my rommate is not a meathead who thinks "all black and white films are boring" or anything like that, he has a pretty good taste and is open to new things. That's why decided on having a classic movie night every week. So I'm asking for you help in curating the program.
Remember, this is not about educating him on the most important/best/influential films of that era, but about choosing ones that are easily watchable by today's standards and tastes.