In terms of dated, I think it would be important to fully acknowledge the existing standards of the day. It wouldn't matter how gritty they would have wanted to make the dialogue, they'd never get a movie into the cinemas if the words like firetruck or even switchhit were used. Let's not also forget massive special effects technology and technology in general. You could take a modern director, put him in a time machine back to the early 40s and he wouldn't be able to make a 'modern' film.
computer generated imagery has lead to a ridiculous plot or two over the years. Consider for example, a recently released film where they are plummeting to earth in a tank, where one of its parachutes break (and frankly even with both of them it likely wouldn't have landed safely) and they 'fly' the tank using the recoil from its main cannon to alter its trajectory and land in a lake, then drive out of it. I'll happily overlook a few minor issues with movies made well before I was born, rather than that nonsense (and to be fair I like action films and a bunch of recent films).
If nothing else, films like this can offer (if we do the movie going equivalent of reading between the lines) an insight into societal values of the time. I'm not suggesting they are a totally accurate depiction, and often plot/dialogue compromises had to be made, but surely I'm not the only one who is given some sort of education from it.
In other ways it is good that it is dated. Imagine if you will a film if it was made this year, but was 'set' in the 1940s. And imagine if they used some sort of trance or other dance music for various scenes. It'll be weird to say the least.
Having said all that, sure this isn't perhaps Bogart's best film, and some of the dialogue is corny.
The weirdest thing I see in gangster films (not related to this one as such) that doesn't 'gel' - it's the visiting sessions in prisons, where they talk on the phone. Having seen a friend who was in (remand?) waiting for trial (ended up being found not guilty fwiw) and visiting there, the darn things are so noisy, even with glass screens between the two, everyone had to yell into the phones, just to hear over the roar. In any movie though, even with crowded visitor rooms, you can hear dialogue clearly. Same goes for scenes shot inside a nightclub with music supposedly booming. I can only think of one show off the top of my head, where the music was loud, and the people speaking couldn't be heard even remotely clearly, and they supplied subtitles instead - which actually worked well, as it gave the sense of people shouting, but others only hearing if they were very close indeed, the rest being drowned out by the music.
I know it's a weird tangent, but the point is that even modern films can get a lot 'wrong' and they don't have to work within half as many restrictions as to the dialogue and content, relatively speaking.
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