My dad is like that as well. He can tell you the make, model and year of a car just based on a glimpse of the tail light.
I can’t nail down the year of a movie unless they say something specific to a year, usually pop culture related. Something along the lines of watching a TV show, going to a movie, hearing a song etc…
But in general terms, along the lines of pre/post 9/11, if a movie takes place in the late 80’s or early 90’s I tend to notice cell phones. Either brick phones be shown as a huge leap in technology for rich people (I think they had them in Wall Street) or the lack thereof. Often times I’ll watch a movie and think about the fact that the entire premise would be ruined if the main characters had cell phones. I can’t think of a good example off the top of my head, but think about how many movies there are where there’s a bad guy after someone and another person knows and needs to get to that person first to warn them. The movie would be moot if they could just call the protagonist and say “Hey, dude’s on his way over, to get the microfiche, why don’t you hop in your car and take a ride for a few hours. I’ll let you know when he’s gone”
Wait, got one. Ferris Bueller. The last scene. Nowadays, Ferris could have called his dad and asked him to pick up some medicine on the way home. That would have bought him plenty of time to get home and into bed.
Plenty of episodes of Friends wouldn’t have been half as funny if they all had cell phones. Of course, it ran from 1994 to 2004 so they really should have, I have to assume they left them out on purpose (did they have them towards the end).