So how far has Miss Moneypenny come over the course of fifty years and four actresses (discounting Barbara Bouchet in the 1967 spoof 'Casino Royale' and Pamela Salem in the non-canon 'Never Say Never Again')?
The longest-serving Moneypenny was the late Lois Maxwell, who starred alongside Sean Connery, George Lazenby and Roger Moore. Considering she never dies, is fully dressed at all times, and always comes back in the next one, Maxwell's Moneypenny winds up treated far better than the other Bond girls of the era. The character didn't exactly evolve much over fourteen films (Maxwell was the second longest-serving actor in the Bond series, behind Desmond Llewellyn's Q), but her playful banter with 007 became as essential a component of the series as the cars, gadgets and girls. Still, by the time she finally stepped down along with Moore in 'A View to a Kill,' few could question that (not unlike Moore) she was too old for the role.
The second and sadly least remembered Moneypenny was Caroline Bliss, who took the role alongside the similarly short-lived 007 Timothy Dalton. Bliss's Moneypenny would seem to be a casualty of the uncertain times into which the Dalton 007 was forged, with all concerned anxious to play things a bit straighter and a lot more politically correct. In 'The Living Daylights,' Dalton's Bond is friendly and respectful toward her, and when Bliss flirts with him, it is almost entirely one-sided (a little buttock slap notwithstanding). Meanwhile, in 'Licence to Kill,' her appearance is so brief it barely registers. While there's nothing inherently wrong with her performance, it's small wonder Bliss's Moneypenny is largely forgotten.
More impact was made in the role by Samantha Bond, who served as Moneypenny alongside Pierce Brosnan. Surname associations aside, Bond proved an ideal fit for this new model of Moneypenny, as - this being the 'new lad' era - the Brosnan films re-embraced the casual sexism of old, with a side order of post-modern irony. 'Goldeneye' saw Moneypenny suggest that Bond's behaviour toward her might qualify as sexual harassment, and in 'Tomorrow Never Dies,' Samantha Bond got to deliver almost certainly the best double entendre ever to pass Moneypenny's lips: "you always were a cunning linguist, James." They found room for a sly nod to the Bill Clinton/Monica Lewinsky scandal when Bond gives her a cigar in 'The World is Not Enough,' and in 'Die Another Day' she even got to kiss him for the first time - albeit in a virtual reality simulation.
Of course, by this point Bond had another notable woman in his life in the form of Judi Dench's M; the only actor to carry over from Brosnan to Craig. Perhaps this explains why Moneypenny was omitted from 'Casino Royale' and 'Quantum of Solace,' only to be re-introduced once Dench's M is killed off. With it now being firmly established that women can wield authority in 007's universe, might Naomi Harris's Moneypenny in some way take over where Dench's M left over; a strong woman to keep him grounded?
