The Connery movies are dated in many ways and getting more ancient every second, but Connery found that perfect balance of action and humor, and the movies reflected that. As the movies started to get silly, so did the sets and outfits and storylines. Moore did a good job with the humor, but he remained in the role way too long.
They tried to pull back with Dalton, but he had no charisma or aloof sex-appeal (riding a rollercoaster with a stupid grin is mostly what I remember). Brosnan should have been better, but his villain's plots were often overly complex and other than Sean Bean and Xenia he didn't have any good foes. The Craig era started fantastic, but never really got off the ground after that -- 16 years, 5 movies, and nothing very memorable amongst them other than Craig himself. Connery did his first 5 movies in 5 years... with much more success.