Flirtatious, efficient and loyal, the cinematic Miss Moneypenny has been a bespectacled girl-next-door (Caroline Bliss), an effervescent, pixie-cut attache (Samantha Bond), and a feisty agent-in-training (Naomie Harris); but above all, she’s been Lois Maxwell, the charming Canadian actress who established and then wholly embodied M’s secretary across fourteen films and three James Bonds.

As 007 has changed through the years, so has Miss Moneypenny, with subtle and obvious attempts to modernize or toughen her up.  Our current Moneypenny, Harris, has moved out of the office shadows and into a more supporting role, which should help propel the plot in the upcoming No Time to Die.

You Only Live Twice: A Lovely Password

One of Maxwell’s best Moneypenny moments came early in You Only Live Twice, her and Sean Connery’s 5th film together.  After faking his death in a Hong Kong hotel room, Bond resurfaces — literally — in a British submarine for further instructions.  M gives 007 his assignment onboard, wherein Moneypenny is tasked with giving Bond the password to contact his counterpart on the mainland.

Moneypenny confidently and dryly enunciates the secret phrase: “I love you”, and asks Bond to repeat it back to her as per agency protocol.  She knows she has Bond trapped, and after 5 movies Moneypenny (and the audience) will finally hear the words she’s always wanted Bond to utter. But, as he’s done with so many dangerous women, Bond uses his boyish charm and (in Connery’s case) Scottish baritone to get away with a reassuring “Don’t worry, I’ve got it."

License To Kill: Keeping The Homefires Burning

Caroline Bliss supported Timothy Dalton as Bond in The Living Daylights and License to Kill, but was particularly flat in the role.  Both she and Dalton struggled with cluttered scripts and uninspired direction, and neither would return after these 2 films.

In one brief moment in License to Kill, Moneypenny did further the plot when M catches her investigating Bond’s whereabouts while pursuing a murderous drug kingpin.  M’s accusation “who authorized this [communique]” is met with a timid Moneypenny admitting she is worried about James. A small moment in the movie, but one of the few times Moneypenny is employed mid-film without Bond close by.

Tomorrow Never Dies: Cunning Linguist

The schoolboy humor of the Bond films feels particularly dated — Connery and George Lazenby carried it well enough, but Pierce Brosnan struggled and Craig mostly forgoes the juvenile quips.

But Moneypenny was given her chance to be crudely amusing in one scene in Tomorrow Never Dies, which was likely meant to show that she could keep up with the boys in juvenile, sexist humor.  After Bond leaves his tryst to get an update from M (Judith Dent), Samantha Bond’s Moneypenny observes that 007 has always been a “cunning linguist” — said with a wink to the camera and an awkward shrug from Bond.

Goldfinger: Moneypenny Throws Bond’s Hat

Fans of the older Connery movies are used to him striding into Moneypenny’s office with a swagger and tossing his hat to the coatrack - a hat he (and Moore) rarely wore — and flirting with her before receiving the life-or-death assignment from M.

But in the classic Goldfinger, not only does Maxwell’s Moneypenny do an excellent job landing his hat, she asks Bond if his mission to capture Auric Goldfinger might include the retrieval of a gold band - “you know, on the third finger of your left hand.”  This small scene helps establish the excitement of his quest for gold and affirms her ability to drive the playful banter with our hero when given a chance.

GoldenEye: Moneypenny Has A Date

Bond films carried the assumption that Moneypenny, and by proxy all non-threatening women, languished about while Bond traveled the world on his dangerous adventures, sitting anxiously by the teletype / phone / laptop for any sign of his return.

In Goldeneye a new Bond (Brosnan) meant a new Moneypenny (Samantha Bond), and the producers were quick to show her as more than a wilting flower.  When Bond comments on Moneypenny’s evening gown during a late visit to MI6 headquarters, Moneypenny says their work interrupted her date, and he may be surprised to hear she isn’t waiting for a reason ”to run down here all dressed up to impress James Bond.” The days of Moneypenny sitting at home pining away for Bond were over.

Diamonds Are Forever: Working In The Field

Bond’s support team — M, Q, Moneypenny — were most often seen in stuffy, baroque London offices, managing the day-to-day bureaucracy while 00 agents executed their brutal missions.  So it must have been a relief for the actors to get away from the studio once in a while, if only to prop Bond up for a few moments.

Maxwell’s second-best moment off the set came in Diamonds Are Forever, where she gives a recast Connery his passport to take the hovercraft from Dover to Amsterdam.  Moneypenny reminds Bond that a diamond would be a wonderful gift, given his mission parameters; but she would happily settle for a Dutch tulip.

Die Another Day: Moneypenny/Bond Kiss

Just like we’ve always wanted to see the Coyote catch the Roadrunner or Spiderman wed Mary Jane, Bond fans have hoped quietly for a romantic moment between Bond and Moneypenny with each new film.

And they did in Die Another Day, where Brosnan’s Bond quietly greets Moneypenny in her office late at night, before a passionate embrace and an ardent kiss that’s been teased for 19 films. However it would turn out to be a ruse — Bond’s Moneypenny was experimenting with the virtual reality equipment Q uses to train spies, and 007 was never there.

Skyfall: A Close Shave

Naomie Harris was the first Moneypenny to be remolded as a Field Agent, and in Skyfall she’s given ample opportunity to get her hands dirty (as we’ll see further below).  Harris is a fine actress, having appeared in blockbusters like Pirates of the Carribean, action thrillers like Miami Vice and Rampage, and smaller films like Collateral Beauty.

In Skyfall, Moneypenny meets Craig’s Bond recovering in his hotel room in Shanghai, and instead of faintly supporting his mission and leaving, as Maxwell and others have done, she waltzes in and proceeds to give Bond an intimate shave with a straight razor. The scene plays out in a sensuous, flirtatious, even dangerous manner, suggesting that Bond and Moneypenny could be spending the night together (off-camera).

On Her Majesty’s Secret Service: Bond’s Wedding

Yes, Bond was once married in On Her Majesty’s Secret Service, and it brought an end to the thrilling, meandering adventure of Australian model Lazenby’s film. Perhaps the most underrated Bond of the first 30 years, OHMSS ended with joy and tragedy, as Bond presumably left the playboy life behind for wedded bliss.

This change in character was wonderfully illustrated by Bond’s farewell to the ever-present Moneypenny, in one of her few scenes outside of MI6.  As Moneypenny ponders the bridal bouquet she’s just caught, she bids a happy, tearful goodbye to her would-be paramour as he whisks his new bride away. Lazenby’s goofy wave back recast their relationship as brother/sister, and their adoration would never be the same.

Skyfall: Agent Down

The pre-credit scenes in Bond films can be the most memorable of the entire movie, and this was certainly the case in Daniel Craig’s third outing, Skyfall.  The film opens with a breakneck chase across Istanbul’s Grand Bazaar and a speeding train, with 007 assisted by a relentless Moneypenny, who’s relaying the details of her pursuit back to M in London.  As Bond battles a well-armed thug atop the train, Moneypenny - who’s now apparently a marksman (marks-woman?) - prepares to target the henchman as they race over a lonely trestle.

The next few scenes are cinematic gold — Moneypenny fires her rifle, Bond falls from the train, the Bad Guy escapes with the stolen data, and Moneypenny quietly says “agent down” to M and the M16 staff listening on the speakerphone.  Cut to M looking out on a rainy, dismal London, wondering how Bond’s mission went so wrong, and queue the first few strains of Adele’s magical theme song.