Drew, I think you are underestimating film camera technology. Most of those classic pictures will have been taken with Leica's, Contax, TLR Mamiyas, Rollies, large format cameras and the like, cameras in their time way beyond the means of most photographers, and with awesome optics, many of which continue to command stratospheric prices.
So no, pre digital cameras were not poor, they were in many cases outstanding, and had a resolution and fidelity that can only matched by medium format digital backs from the likes of Hasselblad and Phase One and excruciatingly expensive optics.
You are right, you can take rubbish pictures with good kit, and good pictures with mediocre kit. But if the same picture is taken with both, you know which one will be better.
I see that Karen's next post has appeared as I was typing this. No-one has ever won this contest with a point and shoot, and I reckon that is the way it will stay.
Whilst I agree with you about grabbing the viewer, I refer you again to this year's winner. A great shot, and as worthy a winner as any, but how would you have taken that with your iPhone?