Moneypenny is M's secretary. She is generally portrayed as being flirted on by James Bond, while having a not-so-secret crush on him that never gets resolved.
- Adapted Out: Like Q, Moneypenny did not appear in Daniel Craig's two first movies, Casino Royale and Quantum of Solace. And like Q again, she was reintroduced in Skyfall.
- Composite Character: The book incarnations of Moneypenny and Mary Goodnight were combined to create the film version of the former. Goodnight was the secretary of the 00 section, and most of the film Moneypenny's flirtation with Bond comes from his interaction with Goodnight in the books. There is another secretary, Loelia Ponsonby, who rebuffs everyone's advances due to their short life expectancies.
- Deadpan Snarker: Whenever Bond flirts with her, she answers his advances with sarcasm.
- Expy: Ian Fleming created her based on Second Officer Monday, Rear Admiral John Henry Godfrey's secretary.
- Flanderization: Moneypenny's intense RETURNED flirtations with Connery and Lazenby might surprise viewers of later installments, considering how one-sided things seemed to get with the platonic Moore and "pining crush" Dalton and Brosnan eras.
- Last-Name Basis: Fleming never revealed the first name of the novels' Moneypenny nor any of her background. Samantha Weinberg's Moneypenny Diaries series, which is a continuation of Fleming's novels, went with "Jane", and gave her a backstory. Skyfall eventually gave her a first name moviewise — Eve.
- Sassy Secretary: The original and the best.
- Sexy Secretary: Seeing how often Bond flirts with her.
- Sleeps with Everyone but You: Bond happily seduces any semi-attractive woman... except for Moneypenny. Though this might not be true for Naomie Harris' version.
- Bond's and Moneypenny's interactions are decisive proof that this isn't equatable with Can't Act Perverted Toward a Love Interest.
- Unresolved Sexual Tension: Much to their dismay, all of the Moneypennys have this with Bond, with the possible exception of Naomie Harris', given the very potent Did They or Didn't They? scene between them in Skyfall. And if it is still unresolved, it might be to his dismay rather than hers — in Skyfall, he tries to undress her at one point before she slaps his hand away, and he's somewhat jealous in Spectre (after another Did They or Didn't They? scene) when he calls her and he realizes that she has a gentleman visitor (a notable reversal of the typical Bond/Moneypenny dynamic).
Played by: Lois Maxwell
Appearances: Dr. No | From Russia with Love | Goldfinger | Thunderball | You Only Live Twice | On Her Majesty's Secret Service | Diamonds Are Forever | Live and Let Die | The Man with the Golden Gun | The Spy Who Loved Me | Moonraker | For Your Eyes Only | Octopussy | A View to a Kill
- Character Aged with the Actor: Lois Maxwell played Moneypenny all the way from Dr. No to A View to a Kill, in 14 movies over 23 years, and it showed. In Octopussy, she notes that she's getting older when she begins training in an assistant, Miss Penelope Smallbone, whom Roger Moore's Bond naturally tries to flirt with as soon as he enters the office.
- Did They or Didn't They?: According to Word of Saint Paul, at least, she and Bond did; Maxwell said she and Sean Connery discussed a backstory where their characters dated years in the past when "Bond was a tea-boy [at MI-6] and Miss Moneypenny was in the typing pool", complete with a romantic country weekend. They gave each other up to put work first, but it's very evident in the chemistry and intimacy she has with Connery.
- Double Entendre: In You Only Live Twice, she tells Bond the password he must use to contact Tanaka in Japan. Said password is "I love you", of course. In the scene before that, she asks him "How was the girl?"
- Hidden Depths: Maxwell's version of Moneypenny remains the only incarnation shown to be a Royal Navy officer (in You Only Live Twice; the fact she's an officer is indicated by Bond calling her "ma'am").
- Last-Name Basis: Her first name is never used. She's just known as "Miss Moneypenny" (or simply "Moneypenny", if you're Bond — in an inversion, she's one of the very few people to call him 'James').
- Mrs. Robinson: With George Lazenby's Bond; Maxwell was 12 years older than him.
- Not Even Bothering with the Accent: Maxwell was Canadian. Her performance as Moneypenny is transatlantic at best. It's also so good, it doesn't detract from anything at all.
- Running Gag: Bond tossing his hat onto the coat stand in her office. Moneypenny does it herself in Goldfinger without even glancing in the stand's direction (a feat so remarkable that Bond does as Eye Take), and it's rather poignantly referenced when Bond throws his hat to her at his wedding in On Her Majesty's Secret Service.
Played by: Caroline Bliss
Appearances: The Living Daylights | Licence to Kill
The Timothy Dalton era Moneypenny.
- Age Lift: From 58 years old Lois Maxwell to 24 years old Caroline Bliss.
- Demoted to Extra: She does appear in Licence to Kill, but, sadly, it's for a much shorter time than usual, and she doesn't even interact with Bond.
- Irony: Lois Maxwell stated she only agreed to play Moneypenny if she didn't have to put her hair in a bun and wear glasses. Then came Caroline Bliss.
- Last-Name Basis: Like Lois Maxwell's Moneypenny, her first name is never mentioned.
- Nerds Are Sexy: In The Living Daylights, she tries to have Bond come to her home by telling him she loves Barry Manilow's music and has a whole collection of it.
- Screw the Rules, I'm Doing What's Right!: In Licence to Kill, she basically goes against her hierarchy and the whole secret service in that she helps a fugitive Rogue Agent, by calling Q to help Bond in Isthmus.
- Sexy Spectacles: The first Moneypenny to wear glasses, and it surely adds to her sexiness.
- Small Role, Big Impact: Her screentime is very short in Licence to Kill. However, her role in the plot is crucial in that it's her who sends Q to Isthmus to help Bond out of fear for his life.
Played by: Samantha Bond
Appearances: GoldenEye | Tomorrow Never Dies | The World is Not Enough | Die Another Day
The Pierce Brosnan era Moneypenny.
- Aside Glance: Verging on Breaking the Fourth Wall when she's deflecting Q's questions about abusing the VR system in Die Another Day.
- Boyish Short Hair: She sports this hairstyle in the Brosnan movies that followed GoldenEye.
- Early Installment Weirdness: In GoldenEye, Moneypenny is introduced as going to work after a date, with a traditionally feminine appereance, but at the same time eschewing the usual Unresolved Sexual Tension with Bond, and stating that she can sue Bond for sexual harassment. In the rest of her appereances, she has Boyish Short Hair, and switches towards more familiar teasing.
- Kiss Me, I'm Virtual: She is the first Moneypenny ever to have kissed Bond on screen in the seriesnote ... but it was only virtual, as she used Q's Augmented Reality goggles to satisfy her wildest thoughts in Die Another Day.
- Last-Name Basis: Like the previous Moneypennys, her first name is never mentioned.
- She Cleans Up Nicely: In GoldenEye, Bond compliments her black evening dress, calling it "lovely" and pondering if she's "dressed to kill."
- Smoking Is Not Cool: In The World Is Not Enough, Bond gives her a cigar as a souvenir from his trip to Bilbao; the first thing she does is toss it in the garbage can.
Played by: Naomie Harris
- Action Girl: This Moneypenny starts as an MI-6 field agent who worked along side Bond before she decided to take a desk job as Gareth Mallory's secretary. Before leaving the field work, she proved that she is a trained sniper, drives like a stuntwoman, took out two mooks with her heels and a metal suitcase and went on to shoot a few more before eventually deciding that fieldwork isn't for her.
- This is undoubtedly because of (or largely influenced by) her accidentally shooting Bond in Istanbul.
- Adaptational Badass: Easily the most action-capable version of Moneypenny.
- Ascended Extra: This Moneypenny has a bigger role in the plots of both the movies she's been in than all of the previous ones. She's introduced as an Action Girl and actively participates in the Istanbul and Macau missions in Skyfall. In Spectre, she provides some help to Bond (bringing him clues from the burned ruins of Skyfall Lodge and helping him identify Oberhauser) and M (being one of his very few loyalists in the climax).
- Canon Character All Along: She's only known as Agent Eve for most of Skyfall, but reveals her last name at the end when she becomes M's secretary.
- Did They or Didn't They?: Skyfall leaves it ambiguous over whether she had sex with Bond.
- Drives Like Crazy: Granted, they were in a chase, but James needs to have a word with her about driving in crowded streets.
- Given Name Reveal: In Skyfall, she's first known as simply "Eve" for most of the film, until her full name is revealed at the end. She's the first Moneypenny to be given a first name in 50 years.
- Never Live It Down: After accidentally 'killing' Bond she's taken off fieldwork, likely forever.
- Nice Job Breaking It, Hero!: She ends up shooting Bond while he struggled with Patrice atop a train, allowing Patrice to get away with the drive containing the identities of underconver NATO agents. Bond doesn't hold any grudge afterwards, as he perfectly knows she did it by mistake.
- Race Lift: Her counterparts in previous movies were all Caucasian.
- Retired Badass: She decides that she's done with field work after the events of Skyfall that almost caused Bond's death, so she takes a transfer to become M's secretary.
- The Reveal: At the end of Skyfall, she states she is not fit for field work, and will remain only in a desk job at MI6. As Bond says that they have not been properly introduced, she says her full name is Eve Moneypenny.
- She Cleans Up Nicely: In Skyfall, Bond tells her "You look beautiful in that dress".
- Took a Level in Badass: Skyfall shows her outside of office / communication work for the first time in the history of the franchise, to say nothing of firing a gun in combat.