I'm going through the list in a haphazard fashion, according to what movies are available and interest whoever at my house wants to watch with me. For the first match-up, we watched Crash and Rain Man (5th bracket from the bottom on the right, if you're following along).
Crash, 2004 (R)
Crash is pretty intense emotionally and does have quite a bit of swearing and some sex. I definitely wouldn't show it to kids who didn't have the ability to watch critically, because there is a lot of racism going on--it's a huge theme in the movie--and I'd be concerned about kids having trouble filtering that. So, my disclaimer is, I watched this with my kids (who are 12 1/2 and 16) and they both got a lot out of it, but that doesn't mean you'd want to watch it with yours.
Several disparate characters' lives get intertwined through the course of the story, which ends up being cool but at first is disconcerting because you're flitting from situation to situation without really seeing a connection except that everyone is more blatantly racist than anyone I've ever met in my life. The main thing I took away from this movie was, "Are people really that mean to each other in LA?" Not that there isn't racial tension in Portland, including systemic racism, and our police department definitely has its issues. But every single person in the movie, with the possible exception of the little girl, had some major issues.
And another thing: Do people really drive that badly in LA? Because that was a heck of a lot of car accidents in 36 hours.
I fell asleep for a few minutes in the middle of the movie. This didn't seem to have any impact on my understanding of what was going on, though I did miss the cause of one of the car crashes. It's okay, though, because I got to see the touching moment that ensued, as well as the exciting special effects moment which was probably the highlight of the movie for Evan.
Rain Man, 1988 (R)
Evan acted like I'd sentenced him to 3 hours of the home shopping channel when I insisted that he try at least half an hour of Rain Man. I just knew he'd like it! For the record, the R-rating is due to f-bombs and some sexual scenes (without nudity).
I saw Rain Man when it first came out and was interested to see how it had held up over time. We know so much more about autism these days that Raymond Babbitt has become a stereotype by now. When the doctor talks about him being high functioning, I had to grit my teeth--a high functioning autistic adult shouldn't be in an institution like that! However, Dustin Hoffman is just amazing in his portrayal, and I felt like, given the time when it was made, the writers did their homework.
It was extremely amusing to see the Tom Cruise type A personality businessman trying to function in the 80s without a cell phone. One of my favorite scenes is when he realizes he needs help understanding his brother, and so he pulls into a town and looks up a psychiatrist in the phone book, then goes to meet with him. These days, a quick google search would have told him all he needed to know. These aspects definitely date the movie, but in a good way.
Overall, I'd say Rain Man is the clear winner. The relationship between the two men has stood the test of time. As for Evan, he has no comment--but he stayed and watched the full movie.
So that's one match-up down, and just 31 left to go!