Apparently Moneypenny is based on a few different women that Ian Fleming knew. In his first draft of Casino Royale, she had a completely different name and was called Miss Pettaval, inspired by the director of MI6's personal assistant Kathleen Pettigrew. Another possible inspiration was Joan Astley, a pretty badass old girlfriend of Fleming's who ran Winston Churchill's Secret Intelligence Centre during the war and was renowned for being warm and welcoming when senior officers came to her office to view top secret papers.
The first actress to play Moneypenny was Lois Maxwell, who flirted her way through a massive fourteen Bond films with Sean Connery and Roger Moore. Although you may think Moneypenny is little more than a lovestruck assistant, the character is actually a Lieutenant in the Women's Royal Naval Service, so clearly she can kick some ass when she needs to.
Caroline Bliss took over the role of Moneypenny in the two Timothy Dalton Bond films, The Living Daylights and Licence To Kill. Bliss was a much younger actress, but hardly appeared in either film at all, with her role essentially reduced to a cameo. Boo.
When Pierce Brosnan became 007, the aptly named Samantha Bond took on the Moneypenny mantle in the next four films. I always had a soft spot for Moneypenny, particularly when I was in college and utterly sick of being single, as I identified with her as being the girl who never got the boy she liked. Of course, that's all changed now, but I was still disappointed when there was no sign of my girl in Craig's Casino Royale.
There were two other actresses that portrayed Moneypenny, but they're deemed unofficial, as the films weren't real Bond movies per se. Barbara Bouchet appeared in the 60s spoof Casino Royale as a frankly outrageously sexy sixties kitten style Miss Moneypenny and Pamela Salem played her in Never Say Never Again.
|Look at Barbara here, for feck's sake. She's wearing what appears to be a see-through bejewelled nightdress when she's meant to be ON BUSINESS. MOST unprofessional. Get your head in the game, woman!|
Apparently, the shiny new Miss Moneypenny will start out as an MI6 field agent, before becoming M's go-to girl, so it sounds like she'll be doing more then sitting at a desk looking pretty. A more than welcome update of the character, I'm sure you'll agree.