Well, I think the Sean Connery films hold up on the whole, but they are products of their time. There are some elements of them that would definitely be frowned upon today. Let's just say that not all his flings are consensual, or the film makers were not particularly sensitive towards cultural differences.
Most of Roger Moore's movies range from okay to unbearable in my opinion. He had the longest run and I think the general consensus is that he started out okay and got progressively worse. I think The Spy Who Loved Me is the epitome of Roger Moore's James Bond; it's campy and has it's share of flaws, but still an okay Bond film.
Dalton, for all the grit, never quite had the charm to play Bond (at least not at the time). I view his films as more boilerplate action movies than true James Bond films. The living daylights is a decent film, but I didn't really care for License to Kill.
Pierce Brosnan doesn't lack for charms, but he's not very believable as a tough guy, and I think his movies start going downhill after a solid debut in GoldenEye. In fact, his last movie, Die Another Day, is the worst Bond movie of them all, in my opinion.
Daniel Craig is batting 500 with his tenure, two very good and two bad ones. See Casino Royale and Skyfall, and skip the rest. Take this assessment with a pinch of salt (and indeed all the assessments in this thread) as I have several relatives who thought Spectre was his best film and I've read plenty of scathing reviews of Skyfall.
Finally, George Lazenby was put into what would otherwise have been a very good Bond film. My problem with the movie is that I never for a second believed he was Bond, but the movie that surrounds him would've been a good Sean Connery movie. It actually gives a lot of backstory (which I think is unnecessary for Bond) and features the perennial Bond villain, Blofeld, like most of the 60's Bond films.
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