2/ To make watching 250+ films manageable, we are starting with the most recent decade, watching one film from that decade, and then moving back in time. So far we've watched: 2010s Moonlight, 2000s Slumdog Millionaire, and think we watch Silence of the Lambs for the 1990s.
3/ The first two movies were AWESOME! After we reach the 1900s, we think we'll spring forward again and watch another film from each decade, again working backwards.
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6/? So far: Moonlight (2010s), Slumdog Millionaire (2000s), Silence of the Lambs (1990s), Tootsie (1980s). It may take us some time to pick just one film from the vibrant 1970s...
7/? For the 1970s, I’m voting for One Flew Over The Cuckoo's Nest, Chinatown, The Spirit Of The Beehive or The Sting. Spirit of the Beehive is one of my most favorite things ever, so see that if you haven’t already.
8/ We ended up watching The Sting for the 1970s and it seemed welcome brain candy compared to the heavy films before. OTOH, now we know what we are going to be working on in the upcoming depression...
9/ These are my votes for the first 1960s film:
Guess Who's Coming To Dinner
Play Time (one of my faves)
Lawrence Of Arabia
The Manchurian Candidate
La Dolce Vita
10/ I should’ve noted before that we are skipping some obvious choices in each decade because we have all seen them fairly recently. YMMV
11/ We ended up watching Bonnie & Clyde for the 1960s, after not finding a great way to watch La Dolce Vita and certain parties admitting they were not ready for a 3-hour movie.
12/ We are playing with the perhaps obvious idea that some of these films "take on" bigger issues than others. For example, The Sting didn't strike us as going much beyond the enjoyable narrative, other than a glance toward class relations in the Great Depression.
13/ Meanwhile, Moonlight and Tootsie both explore gender and sexuality head on — perhaps with differing levels of success... Our little group has rated Slumdog Millionaire the top film we've see so far.
14/ To catch up, we finished out our first run through the decades with:

1950s: Vertigo
1940s: Double Indemnity
1930s: You Can't Take It With You

We also decided we didn’t have appetite to take on the silent era now, so we are only watching films from 2010s–1930s.
15/ Starting again from the top, we've watched:

2010s: Birdman (whoa, that was different!)
2000s: The Depahted (see what I did there?)

Next up for the 1990s, I'm suggesting we pick from:

American Beauty
The Sixth Sense
Shakespeare In Love
Fargo
The English Patient
16/ Slumdog Millionaire is still holding out as our top-rated movie so far.

I will say that I see a lot of You Can't Take It With You in #WesAnderson's films...I guess I'm probably not the first person to notice that connection.
We ended up watching Fargo for the 1990s. It wasn't as good as I remember it. It was also not really a comedy — not sure why I was remembering it as hilarious — it seemed very dark this time around.

For the 1980s, I'm suggesting:
Do The Right Thing
The Last Emperor
Blue Velvet
19/ We ended up with Do The Right Thing for the 1980s this time through, and I'm glad. It's such a unique, great movie. Hard to believe it didn't get any Oscar love.

For the 1970s I’m suggesting 1 from this short list:
Annie Hall
One Flew Over The Cuckoo's Nest
Chinatown
Cabaret
20/ A note on Annie Hall & Woody Allen. I haven't been able to stand Allen or his work for some time, even before his recent (deserved I think) dive in esteem. OTOH, I think it would be hard to consider oneself "well-watched" in US film w/out having seen at least one of his.
21/ If I'm going to have to watch an Allen film, I'd rather see Zelig or something early like Take The Money And Run, but they're not on the list, and we follow the list. At least Annie Hall is not Manhattan or The Purple Rose Of Cairo or Hannah And Her Sisters or anything later.
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