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Carefully considered analysis of the Bonds can be found from Buffy's villianous Triumvirate:

JONATHAN: Where're we going?
WARREN: To Final Jeopardy. Where Buffy's the one in jeopardy.
ANDREW: We are really super-villains now, like ... like Dr. No. (Jonathan grins)
WARREN: Yeah, back when Bond was Connery, and movies were decent.
JONATHAN: (scornful) Who remembers Connery? I mean, Roger Moore was smooth.
WARREN: You're insane. You're short, and you're insane.
ANDREW: I like Timothy Dalton!

Warren smacks Andrew upside the head.

ANDREW: Hey!
WARREN: Don't make me pull over, okay?

WARREN: (to Andrew) Connery is Bond. He had style.
JONATHAN: Yeah, but Roger Moore was funny.
WARREN: Moonraker? The gondola turns into a hovercraft? It's retarded. Besides, the guy had, like, no edge.
ANDREW: Dalton had edge. In Licence to Kill he was a rogue agent. That's edgy. (Warren and Jonathan give him looks of disbelief)
And he was amazing in The Living Daylights.
JONATHAN: Yeah, which was written for Roger Moore, not Timothy Dalton!
WARREN: (annoyed) Okay, this is stupid! We're wasting time. End of discussion.

The other two nod and turn to their consoles, begin typing. Beat.

WARREN: (very angry) I mean, there's a shot of like *pigeons*, doing double-takes when the gondola blasted by! Moonraker ... is inexcusable.

The others just look at him.

WARREN: Connery is the only actor of the bunch.
ANDREW: Timothy Dalton should get an Oscar and (yells) beat Sean Connery over the head with it!
WARREN: (grimly) Okay, that's it.

Warren spins around, grabs Andrew, gets him in a headlock.
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I think after the initial impressive entertainment of Connery's first several films, the franchise stumbled along the way.
Despite that, it's very hard for me to feel disappointed for long, because there's always elements to enjoy even in the lamest Bond movies.
Whether it's the villian or some one liners, or the costuming, there's always something that feels yummy - like bad-for-ya comfort food.
I actually think the production values on some, I'm thinking a few of the later Moore ones, were not up to what one might expect for such supposedly blockbuster flicks. Some scenes looked downright slapped together.

Moore definately took it in a comedic, lightweight direction, and though on its own merit I enjoyed that,
compared to the others I find those movies the weakest because of such handling.

I would rate Connery's first 4, let's say, the best, with Dalton a close second. Connery gave the perfect blend of deadly serious and breezy zingers.
Dalton took Connery's serious angle to 100%, even the cheesy lines I think he tried to pass off as something a Dark Bond might really think at the time.
My only problem with the Dalton Bond films were the female love interests. The first one was adequate but I recall much buzz when the flick came out that because of the height of the AIDS scare at the time, even the promiscuous James Bond was keeping it down to one sex partner. I thought that was a mistake. BOND MOVIE = BEAUTIFUL WOMEN ... plural.
The second film had the wonderful Talisa Soto as the Villian's (played by the awesome Robert Davi) lover who charms Bond,
but Cary Lowell as the Good Girl CIA operative was talentless and really dragged the whole thing down.
By the way Davi's character's sidekick was so delightfully wicked and showed such great potential talent.
Who was it? Why, oscar winner Benecio Del Toro.

Brosnon's I'm ambivalent about - I think they had some of what was great about Connery's but damn it - some of his stories reeeeeeeeeeally lagged in the middle.

I like every stitch of Craig's new "real" Bond. My only quibble is I don't know why on earth they wouldn't color his hair dark for the role. Bugs the living sh!t outta me.

Joxerfan once posted a wonderful picture of the ... scary looking ... musician I think it was, that Flemming wrote of, that resembled what Bond was supposed to look like.
Joxerfan, buddy - you still have that pic?

BTW - have to disagree about Xenia Onatopp as a cool femme fatale.
I thought Brosnon's time at the wheel clashed with the ridiculousness of her "skill" - being able to suffocate men with squeezing thighs.
That kind of thing belonged with Bambi and Thumper from the Moore days.
And her sexual excitement while doing it was cringeworthy.
I happen to really like Famke Janssen as an actress, and she did the best she could with the material (and she was gorgeous), but it was flat out stupid.
They were trying to be daring in the sexual angle, but it didn't work IMO.

Oh and smutterly - I find Sophie Marceau's scene with Brosnan at the top of the stairs to be one of the finest dramatic moments for a Bond film and, just in terms of drama in movies overall- very fine.
The tragedy of Bond shooting her - it was a: Wow - they really went there - moment. Quintessentially dark.
I thought her character and her situation was very well done, and fit in with what Bond would really encounter in the cases he takes on.
And she was so beautiful and appropriately "troubled good girl" sexy for the Bond genre.