In James Bond movies, the cinematic Miss Moneypenny was Flirtatious, efficient, and loyal. She has been a bespectacled girl-next-door (Caroline Bliss), an effervescent, pixie-cut attaché (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 Bond actors.

As 007 changed through the years, so has Miss Moneypenny, with subtle and obvious attempts to modernize or toughen her up. The most recent Moneypenny moved out of the office shadows and into a supporting role. This allowed Naomi Harris to portray the character in a much more active way, allowing her to get involved in the action and even almost kill Bond on one occasion. By No Time to Die, Miss Moneypenny proved she was a loyal and fierce friend and ally to 007, and she proved that she really cared about the man she was sworn to assist in saving the world more than once.

You Only Live Twice: A Lovely Password

James Bond with Miss Moneypenny in You Only Live Twice.

One of Maxwell’s best Moneypenny moments came early in You Only Live Twice, her fifth film in the franchise. After faking his death in a Hong Kong hotel room, Bond resurfaces 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.

RELATED: 10 Best James Bond Movies For Beginners

Moneypenny confidently and dryly enunciates the secret phrase: “I love you,” and asks James Bond to repeat it back to her as per agency protocol. She knows she has Bond trapped. After five movies, Moneypenny thought she would finally hear the words she’s always wanted Bond to say. However, as he’s done with so many dangerous women, Bond uses his boyish charm to get away with a reassuring “Don’t worry, I’ve got it."

License To Kill: Keeping The Homefires Burning

James Bond with Miss Moneypenny in License to Kill.

Caroline Bliss supported Timothy Dalton's James Bond in The Living Daylights and License to Kill, but remains mostly unmemorable in her appearances. Neither she nor Dalton would return after their two James Bond films in the series. However, Moneypenny had at least one interesting moment in the two movies.

In License to Kill, Moneypenny furthers the plot when M catches her investigating Bond’s whereabouts while pursuing a murderous drug kingpin. Moneypenny admits she is worried about James after M asked “who authorized this?” This remains a small moment in the movie, but one of the few times Moneypenny appears mid-film without James Bond close by.

Tomorrow Never Dies: Cunning Linguist

James Bond with Miss Moneypenny in Tomorrow Never Dies.

The schoolboy humor of the James Bond films feels particularly dated at times. While Sean Connery and George Lazenby carried it well enough, 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. This showed she could keep up with the boys in juvenile, sexist humor. After Bond leaves his tryst to get an update from M (Judi Dench), Samantha Bond’s Moneypenny observes that 007 has always been a “cunning linguist.” She says this with a wink to the camera and an awkward shrug from James Bond.

Goldfinger: Moneypenny Throws Bond's Hat

James Bond with Miss Moneypenny in Goldfinger.

In the older Sean Connery movies, James Bond would stride into Moneypenny's office with a swagger and toss his hat to the coatrack - a hat he rarely wore. He would then proceed to flirt with Moneypenny 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. It was proof that Maxwell's 14 appearances as a supporting character in James Bond movies were well deserved.

GoldenEye: Moneypenny Has A Date

Moneypenny wishes Bond luck before his meeting with Xenia Onatopp in GoldenEye

James 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. The idea is that they sit anxiously by the phone awaiting any sign of his return.

In Goldeneye, Pierce Brosnan's first appearance as James Bond also meant a new Moneypenny (Samantha Bond), and the producers quickly showed she was 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. She said 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

Miss Moneypenny in Diamonds are Forever.

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. It was nice to see the characters get away from the office once in a while - if only to prop Bond up for a few moments.

RELATED: The 10 Most Realistic James Bond Movies

In Diamonds Are Forever, Maxwell's Moneypenny gives Connery's Bond 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. However, she would happily settle for a Dutch tulip.

No Time to Die: Mourning A Lost Agent

The end of James Bond No Time to Die.

In what might be the most shocking moment of any James Bond movie, the lead character died to save the world at the end of No Time to Die. This made Daniel Craig the first actor to die as James Bond. After the sad moment when James said goodbye to Madeleine, the movie moved to a moment at M16.

This was unlike almost any other Moneypenny scene in the franchise. With M, Q, Moneypenny, and Bill Tanner in the office, they shared a drink to James Bond's memory. While this was M's moment to deliver his Jack London quote, Moneypenny giving her cheers was a perfect moment as they all remembered what made James such a great agent.

Die Another Day: Moneypenny/Bond Kiss

James Bond kisses Miss Moneypenny in Die Another Day.

For years, the James Bond franchise teased audiences with the idea that Bond and Moneypenny might one day hook up. In every movie, it seemed the chances grew slimmer, but there was always a hint that the two could be more than just allies. Finally, the franchise offered that romantic moment between Bond and Moneypenny.

In Die Another Day, Brosnan’s James Bond quietly greets Moneypenny in her office late at night. The two then share 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. This was all for her own enjoyment.

Skyfall: A Close Shave

James Bond with Miss Moneypenny in Skyfall.

Naomie Harris was the first Moneypenny to work as a Field Agent. In Skyfall, she receives ample opportunity to get her hands dirty. In this James Bond movie, Moneypenny meets Craig’s Bond, who is recovering in his hotel room in Shanghai.

RELATED: Every James Bond Actor, Ranked By Faithfulness To The Source Material

Instead of faintly supporting his mission and leaving, as Moneypenny did in past movies, she walks in and proceeds to give Bond an intimate shave with a straight razor. The scene plays out in a sensuous, flirtatious, and even dangerous manner. The scene also suggested that Bond and Moneypenny might have spent the night together.

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

Miss Moneypenny in a hat in On Her Majesty’s Secret Service.

Bond got married in On Her Majesty's Secret Service, and it brought an end to the thrilling adventure of George Lazenby’s film. Perhaps the most underrated Bond of the first 30 years, OHMSS ended with joy and tragedy, as Bond 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 was never the same.

Skyfall: Agent Down

Naomie Harris as Moneypenny in James Bond Skyfall.

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 fights a well-armed thug atop the train, Moneypenny prepares to shoot the henchman as they race over a lonely trestle.

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.

MORE: Every Daniel Craig Bond Movie, Ranked (According To Rotten Tomatoes)