Super-spy James Bond has had plenty of love interests over the years, but none can compare to his trusty secretary Miss Moneypenny — and the many actors who have played her. Since his first appearance in 1962’s Dr. No, played by a suave young Sean Connery, super-spy James Bond has survived countless dalliances and ill-fated affairs with a veritable bevy of so-called 'Bond girls', often going through multiple love interests throughout a single cinematic outing. Most haven’t been so lucky, as it is practically a tradition for all but one of his love interests to meet an untimely end before each James Bond movie finishes.
In the case of George Lazenby’s singular and unusually heart-wrenching Bond outing - On Her Majesty's Secret Service - even the woman 007 married didn’t survive to see the end credits of the movie. However, despite this rule, there is in fact one Bond girl who has managed to survive her proximity with the super-spy despite this formula, perhaps because the pair never actually consummated their flirtatious relationship. She's been a secretary, assistant, and even a fellow field agent, but one thing Miss Moneypenny has never been is disposable.
From the classic Lois Maxwell to the short-lived Caroline Bliss, it’s worth taking a look back at the only Bond girls who aren’t technically Bond girls to see how the James Bond franchise has transformed over the decades. Like the star himself, Moneypenny was only actually given a proper James Bond backstory in the Daniel Craig era. Until then, the character was an unobtainable source of sexual tension for Bond, perhaps the only woman in the franchise who he wouldn't woo effortlessly, but also something of an enigma herself. Despite their rapport, the pair's chemistry never went further than that in the entire twenty-five film James Bond series - as though the jury is still out on Skyfall, nothing happens onscreen at least. Like Bond himself, Moneypenny has at various points been campy, tough, realistic, reserved, and over-the-top, and the character's transformations over the years give an insight into the changing face of the spy franchise as it entered the twenty-first century.
Lois Maxwell
The original, the longest-standing, and forever the greatest, Lois Maxwell’s Miss Moneypenny remains the reigning queen of Bond’s many onscreen assistants. With a tenure that stretches from the influential original Bond Sean Connery’s debut through to the later, campier efforts of an aging Roger Moore, Maxwell maintained consistent chemistry with two Bonds and effortlessly switched her deadpan, reserved demeanor to match two very different actors and their contrasting interpretations of the super-spy. A crucial figure in the early years of the franchise, Maxwell’s Moneypenny was established from the jump as Bond’s lone white whale, the one woman who he couldn’t have and, as such, the woman he felt most free (and compelled) to outrageously court.
Maxwell went through plenty of campaigning to secure the role as she needed the financial support of a steady job due to her husband's poor health, and the actor was almost replaced when she demanded a pay rise from Bond producers once the series was a success. It's a good thing the raise was secured, as few actors could have made Bond's early, fun films as enjoyable as Maxwell's charming Moneypenny. It's a difficult balance for Maxwell to nail, never seeming too available but never too cold or aloof, and the actor’s performance across 14 films somehow stayed consistently entertaining despite the wildly different tones (and quality) of these installments. Some of the character’s most infamous pick-up lines were first offered to, and smilingly rebuffed by, the unflappable Moneypenny Maxwell played, and the actor’s reserved, subtle smirk remains the enduring image that most James Bond fans picture when they hear the character’s name.
Caroline Bliss
There’s nothing wrong with Caroline Bliss’ portrayal of Moneypenny in her pair of appearances as the character, in the relatively grounded and edgy Timothy Dalton Bond movies Licence to Kill and The Living Daylights. However there’s also nothing wrong with Dalton’s harder-edged, more realistic Bond (a big influence on Daniel Craig’s later interpretation of the character), but much like Bliss’ Moneypenny, few would cite the Hot Fuzz star as their favorite version of the slick super-spy. Through no fault of their solid turns, both Dalton and Bliss' limited contributions to the James Bond franchise just lack the longevity enjoyed by their competitors. Bliss and Dalton only managed to eke out two Bond movies and, although both movies are commendable, entertaining efforts, there’s no denying that as a result, Bliss left the least lasting impression on the character.
Samantha Bond
Samantha Bond is the perfect moniker for an actor in this franchise (and particularly one who fans love to pair off with James). That said, it’s more than nepotism that made Goldeneye's James Bond fall for his namesake Samantha. Whether it’s her sparkly rapport with Pierce Brosnan’s campy Bond, her in-car office set-up, or Goldeneye’s rare, casual glimpse into her life outside the office, Bond’s Moneypenny fleshed out the character in a way Bliss never had the opportunity to. The actor proved more than up to the role, but unfortunately, her legacy did suffer thanks to Die Another Day’s embarrassing virtual reality tryst, which sees the secretary fantasize about finally consummating her crush on Bond.
A big part of the character’s enduring appeal is that, without any significant insight into the real-life origins of Bond and Moneypenny, it’s impossible to tell how much of their flirtation is deeply felt and how much is workplace banter. Die Another Day was a failure for many reasons, but chief among them was this sort of misguided fanservice which made the unspoken sexual tension way too obvious and left their relationship feeling listless as a result. Luckily, it wasn’t long before the James Bond series was reinvented and the franchise didn’t have time to damage Samantha Bond’s otherwise solid iteration of the character before she was replaced.
Naomie Harris
The current incumbent of the role, Naomie Harris' Miss Moneypenny is technically far from over just yet - and, whether or not Tom Hardy replaces Daniel Craig in the role of Bond, there’s no knowing whether she’ll remain in the role going forward. Nonetheless, it’s at least clear that, with a new first name of Eve and a more substantial role in 2012’s Skyfall, Harris’ Moneypenny is among the best of the various interpretations. Initially working as a field agent until an impossible decision leaves her accidentally risking Bond’s life, Harris’ Moneypenny is a tough, independent, and strong-willed reinterpretation of the character. Luckily, Harris adds in this edge without losing any of the character’s cheesy charm and can pull off an eye-roll with the best of them (despite Craig’s taciturn version of James Bond spending more time brooding than quipping).
