It took a while, but I finally finished all 20 movies, along with the non-Eon vehicle, in the original James Bond series. Every movie is pretty much a formulaic product of popular culture that becomes a blur after a while, so instead of a review of each individual movie, I will simply write about each era, and what I think is the best and worst movie from it.
Sean Connery
He is the quintessential Bond, and by far my favourite rendition. Fleming may have been horrified by his casting, as Connery was far from the distinguished Englishman that he had imagined, but his charisma, physicality and sex appeal made the role his own. Others may try to take a different route, but I feel that they basically build on the template he established. In fact, a 52 year old Connery, 12 years removed from his last outing as Bond, was still vastly superior to Moore in 1983, when both starred in their own Bond vehicle. Furthermore, even though he had been criticized for his misogynistic views and treatment of women, four of the more memorable Bond girls came from his tenure as Bond. All in all, despite some cringe-worthy moments, especially from today's viewpoint, and some pacing issues, as they all tend to drag in the middle, his movies still rank as the best Bond movies, even today.
Of his seven turns as the superspy, the best movie is Thunderball. Bond is known for his fast cars, fun gadgets, and great stunt pieces today, and this one is the first to feature all three. Add to the fact that it has a fun plot, a great henchman, and a memorable Bond girl who actually has a personality, it is clear that this is the Bond formula all subsequent movie tries to follow, but none has reached. Even the unofficial adaptation of the same book, Never Say Never Again, is not half bad as a 80s update of the movie, and will certainly be ranked as one of the better Bond movies if it qualifies. From Russia with Love and Goldfinger are great too, but they do not check all the boxes.
The worst is the follow-up, You Only Live Twice. Ronald Dahl wrote the screenplay, but he showed that success in one form does not automatically translate to another. There are a lot of plotholes that pretty much render the movie nonsensical, and worst of all, it is downright racist, since the yellowface Bond donned is unnecessary. Blofeld, Bond's archenemy, finally shows his face, but Donald Pleasence plays him like a scared rat, which just undermines his supposed fearsomeness that the previous two movies established. Honestly, I am surprised that this one did not downright destroy the franchise, because I rank it the worst of the 20 movies.
George Lazenby
People gives Lazenby a hard time for his lone tenure as Bond, but Lazenby's performance is actually rather interesting. At first, it is clear that he simply wants to emulate Connery, but he fails miserably, because he just does not have the natural charisma and confidence of Connery. However, as the movie progresses, that supposed lack of confidence actually helps, as he shows an inherit vulnerability, and that humanizes Bond. Bond is still a superspy, but in this outing he shows that he is human, and that actually makes him relatable. In fact, nowadays, On Her Majesty's Secret Service can be seen as underrated, because it has arguably the best Bond girl, and as the closest adaptation to the original novel, it can also be seen as the best written movie in the series. Furthermore, Lazenby becomes a what-if scenario, because I actually want to see more of him, and I do wonder where he will take the series if he actually did more than one.
Roger Moore
Personally, I hate Moore's take on the Bond character, because his Bond becomes nothing more than a modern Casanova who will resort to trickery in order to get laid. In fact, the majority of his seven movies would be at the back end of the rankings, as they are pure popular entertainment that simply try to piggyback off of popular trends, from Blaxploitation in Live and Let Die, martial arts in The Man with the Golden Gun, and then Star Wars in Moonraker, the plot is so formulaic that they are pretty much interchangeable with one another, and they feature some of the worst and vapid Bond girls ever. That said, I cannot deny that he has put his own stamp on the character, since he is one of the most well-known portrayer of Bond along with Connery, and people also do like his more comical approach, as all his movies made a cumulative one billion dollars at the box office. Under Moore, Bond truly becomes iconic, and he also helps to slowly shepherd the character to a grittier direction in the 80s, so despite all his flaws, he is still an important asset to the franchise.
It is actually hard to pick the best Moore vehicle, because they are all pretty much the same, but if I have to choose, it will probably be For Your Eyes Only. Most people pick The Spy Who Loves Me, and that one is actually Moore's own personal favourite, but while it certainly has the most interesting concept, since it features Bond's Soviet counterpart who is a woman, his equal, and holds a personal grudge towards him, and Jaws is a very memorable henchman, it is ruined by Moore's lack of acting ability that fails to convey complex emotions, and the notion that Bond has to be superior. Frankly, it should have been better than it actually was, and I see it as a missed opportunity. For Your Eyes Only is a rather gritty take on the character, as the Bond is closer to the original novel, and it is, at that point, the best paced and choreographed movie in the series yet. In fact, he fits in rather well with all the action heroes of the era, and despite its weak Bond girl, as usual, a useless character in the figure skater that just takes up screentime for no reason at all, the fact that Moore finally begins to show his advanced age and is rather slow in some of the action sequences, it becomes the formula for the Bond movies from that point on.
The worst is definitely Moonraker. This one is just so ridiculous, especially the really suggestive Bond girl name, along with the laser fight and zero gravity love scene, that Bond becomes a parody. Furthermore, Bond actually willingly commits mass murder here, when he does not even try to save the inhabitants of the space station. In fact, it is the reason why the series has to do a 180 and go back to its grittier roots in the next movie, For Your Eyes Only, because even the producers know that they went too off the rockers. Critics then and now killed A View to a Kill, and while it has one of the worst and useless Bond girl in Tanya Roberts, along with a boring ending fight sequence as the protagonist and antagonist engage in a shoving match, it has a good pace that keeps the movie entertaining, and Walkens and Grace Jones are really fun to watch.
Timothy Dalton
Dalton's tenure is a rather complex case, to be honest, and that makes him hard to judge. Back then, his gritty and dark version is so different from the templates his predecessors has established, that audiences largely rejected him, and the movies suffered from diminished returns. After his tenure, another Bond movie did not come to market for 5 years, so rightly or wrongly, he got the majority of the blame as the one who almost killed the franchise. Nowadays, however, most people like that he took Bond back to the novel roots, and consider his portrayal to be ahead of his time. His two Bond movies, in fact, are seen as overlooked gems. Personally, I think he is somewhere in between the two assessments. After Moore's last critically reviled stint, it is clear Bond needs a change. Since the series is very much a product of its times, and back then, the Schwarzeneggers and Stallones were the ones who dominated the action market, so Bond took on some of their characteristics. He became harder and edgier, but in the process, he lost a lot of that signature Bond charm. At times, he even looks more like a villain than hero. While he was still passable in the first movie, The Living Daylights, he just looked completely out of place when he morphed even more into his contemporary heroes in License to Kill, his second stint where he took a no-nonsense one man army approach. Suddenly, he was no longer likeable, and the usual Bond formula no longer worked. Thus, even though I am actually not that high on Dalton's portrayal, because he simply cannot pull off the 80s hero audience want, he is frankly more of a victim of the times than anything. He came into the role at a time when audience's tastes changed, but the producers continued to rely on a old formula that did not work for the change. In essence, he was simply a case of a square peg in a round hole.
That said, despite my misgivings of Dalton's performance, especially in the second one, I cannot say either movie is bad. The action sequences finally matches the standards of other big budget flicks of the era, and along with a modern high speed pace that keeps up with the action, they largely cover up for Dalton. I also like that the Bond Girls are actually capable and not just mere damsel in distress, so that is a much welcome change. Thus, they rank up there as some of the better Bond movies. While most people like License to Kill, because it is so different from every other Bond movie in the original series, I prefer The Living Daylights as Dalton's best outing, which is also what Dalton himself chooses. Most importantly, he maintain some of Bond's charm, and as a result, when he slows down to romance the female lead, it actually does not feel too out of place, since that is the usual formula. In License to Kill, those moments actually break the pace of the extremely high-octane movie, and I blame the producers more for the failure. Frankly, they should have gone all in on the action, and it would have been a much better movie. It has the better villain and Bond Girl to boot too.
Pierce Brosnan
Personally, I find him rather boring as Bond, because he is basically a mix of Connery and Moore, and he really does not bring anything new to the table. The writers tried to bring more depth to Bond, but those are all through dialogue and not action, and that is just not believable. Plus, his movies, like Moore's, are so formulaic, that they feel one and the same. Still, his modern update is just what the franchise needed in the 90s, and he deserves a lot of credit for the box office success. People want mindless action movies with a likeable lead, and they got it in spades with this Bond.
Thus, I really do not have a favourite with Brosnan. They are all bottom half to bottom quarter movies, and very forgettable. If I really have to pick, it will reluctantly be Goldeneye. Honestly, the movie has some issues, with the biggest being that Bond goes on a vacation, in the middle of the mission. Not only does it not make sense, it causes the pace to fall completely off. Also, even though the villain and henchwomen are two of the best in the series, and they even steal the show, they have rather short on-screen time, so that is a disappointment too. Still, it is the movie that revived an almost dead franchise, and the others are worst, so it takes its place as lead by default.
The worst has to be Die Another Day. As the 20th official Bond movie, there are a lot of Easter eggs of previous Bond adventures for Bond fans, but other than that, there is very little to like. From the surfing entrance into North Korea, the plot device where gene therapy can change an Asian character to a Caucasian one, which coincidentally is also racist, very obvious CGI, to a sudden slowdown of camera speed that does not do anything, the movie is so ridiculous and over-the-top, that it feels like a parody. Brosnan does not help either, because in the first half of the movie, he actually looks like he has blueballs, and that is not an image anyone needs. It is no wonder that the franchise has to be re-booted, because no one can come back from it.
Overall, the original Bond series is just popular entertainment. Certain movies can be fun, and they reflect the taste of audience at the time of release, but other than that, there is very little re-watch value because it is a straight formula. In every movie, it is basically a detective story, and it always starts with Bond far behind the plot, as he investigates. By the halfway to the 60% point, he will figure out everything, either by himself, or the villain will straight up tell him, and he spends the last portion to thwart the evil plan. Sometimes he is betrayed, and sometimes he finds unexpected allies, but in the end, Bond succeeds, and he walks away, usually with the girl. I did it once, and that is enough for me. That is why I did not re-watch the Craig era. Again, once is enough.