No One Should Ever Have Played Moneypenny After Lois Maxwell
I've been saying this for years: after Lois Maxwell left the series, they should have just retired the Miss Moneypenny character altogether. She really did embody that role and I don't feel it's one that could ever be recast. The reasons that different versions of Bond, M, and Q have all worked is because those characters actually play major roles in the plot and so you always need them. Moneypenny, on the other hand, never really directly affects the plots: instead we just like her because she's an endearing character. She's someone who's attracted to Bond, but they also have a special friendship that's unique. Lois Maxwell created something that couldn't be recreated.
Opposite Sean Connery, she was great. Perfect chemistry, perfect flirting and innuendo, and they just feel like classic scenes. Opposite Roger Moore, the chemistry wasn't as strong, but it still was always nice to see her as Lois Maxwell was just so likeable and a hallmark of the franchise.
As for the other actresses, Pamela Salem and Caroline Bliss both just played Moneypenny as a mousey librarian. Samantha Bond was a little better and gave her more sass, but left fairly little impact. As others have said, the scene in DIE ANOTHER DAY where she has a virtual reality fantasy of Bond seducing her just felt like a violation that went against what the character had always been about. All of these actresses could have been completely cut from their respective films and you wouldn't have even noticed it. Naomie Harris has been the most unique new take on the character, but I don't really buy her origin story.
Because Moneypenny is a character we like not as a plot point but as a personality, only one version of the personality was able to really leave an impact.