Watch em all in order of release. Yes they are a product of their time but watching the new ones first is only going to confuse things. Ignore all these Craig fanboys.
They are live action "Man's Man in the Cold War" cartoons with a sprinkle of Britain wishing it was still relevant in world events, and should not be taken too seriously. Watch em like that and you'll appreciate them a little more.
Also watch them with the understanding that the world is a whole lot smaller than it used to be. Things like the Internet were so far beyond what most people could even begin to conceive of for most of the franchise, jet travel was still in its infancy when this thing really kicked off and people didn't really expect to see Hong Kong or even the Bahamas, so seeing them in a movie was almost as good. Bond really capitalized on that. MI6 and the CIA must have super fancy gadgets that nobody has ever seen, because how else are they going to spy on people. Etc. And when you get into the villains, each of them had to have their own lair. Seeing what Ken Adam would come up with for the next one was always a treat, until they went away from it.
Lastly the quality really varies after each Bond is introduced. Each new Bond gets a good or great movie, and then it's up and down until the franchise recasts. It even happens to Craig. You should probably stop at Goldeneye. It's the last really great Bond movie.
