It's the 20:20 Movie Frame Game of 2019!

…is the correct answer!

60:

80:

100:

And yes, that’s Fred in blackface in the 80, performing his tribute to Bill ‘Bojangles’ Robinson.

Over to you, @charmtrap .

Let’s stick with the ‘old movies with racist sequences’ theme.

20:

Holiday Inn?

That’s The Chappelle Show.

Neither of those things.

40:40

That almost looks like Spencer Tracy in a priest collar but I can’t remember in which movie he played a priest…

He played priests several times, IIRC, most famously in Boys Town. It’s not any of ST’s priest pictures, though, sorry.

Nothin, eh.

60

Man, you guys are bad at this. Here’s one with the stars of the piece front and center.

80

Is that… Bogart?

There’s no way this can be right, but I’ll toss out High Sierra.

That looks like the car from The Big Sleep, but nothing else about it seems right.

High Sierra it is! Excellent early noir, starring Bogie as a sentimental gangster and Ida Lupino as the dame. Good one, not to miss.

No more shots…your go @Gordon_Cameron.

Well knock me down with a feather. Of course I’ve heard it was his breakout role, but never seen it.

New 20:

It’s that guy from that movie.

Oops, wait, I think I know it…that’s Matchstick Men, I think.

Geez, good eye. It is Matchstick Men! I’ll post the other frames when I get back to my PC.

The 40, 60, 80, and 100: