Miss Moneypenny is one of the most critical allies thatJames Bondworks with, as she serves as the secretary to M, and one of the most critical figures in all of MI6. The Bond franchise has a somewhatshaky relationship with women, and the flirtations between 007 and Moneypenny have been endlessly debated by hardcore fans of the series. Although some depictions of their relationship seemed to suggest that Moneypenny longed for Bond, many of the more modern installments established her as an independent ally and confidant. Similar to side characters like M, the gadget expert Q, and the American CIA agent Felix Leiter, Moneypenny has been portrayed by many different actresses over the course of the franchise’s history.
Moneypenny had her origins in the original novels by Ian Fleming, but the character has been significantly expandedover the course of the franchise’s history.Subsequent films established that she had her own history in field work for MI6, and many of the more recent Bond novels not written by Fleming put her in the spotlight. While there is still a lot of anticipation regarding who will play Bond next afterDaniel Craig, there is also a serious question about who the next Moneypenny will be. Here is every actress who portrayed Moneypenny in the James Bond movies, ranked.

6Barbara Bouchet
Appeared in: ‘Casino Royale’ (1967)
It’s almost hard to compare Barbra Bouchet’s performance as Moneypenny to the other actresses, as she appeared only once in the non-EON produced Bond filmCasino Royale. Due to a strange incident regarding the rights to the series, Warner Brothers was able to produce their own version of the first novel in Fleming’s series, but decided to make it into acompletely outlandish parodythat featured several different actors cast as Bond and M.
Bouchet’s appearance inCasino Royaleis really only there to parody the other films, as the film makes fun of the strange dynamic thatSean Connery’s Bond had with Moneypenny in the films that he appeared in.Casino Royaleisn’t really a film that has aged well, as the jokes made at the expense of the Bond franchise at the time feel completely out of touch now. While it’s one of the worst films ever made based on Fleming’s material, Bouchet can’t be blamed for doing the best with what was not very strong material to begin with.

Casino Royale
5Pamela Salem
Appeared in: ‘Never Say Never Again’ (1983)
Pamela Salem has only one opportunity to appear as MoneypennyinNever Say Never Again,the second of two Bond films that were not produced by EON and the Broccoli family. Due to a strange occurrence regarding the rights to the novelThunderball, Warner Brothers andThe Empire Strikes BackdirectorIrvin Kershnerwere allowed to make a remake, which brought Connery back into the fold as an older version of Bond. WhileCasino Royaleis a complete disgrace to the character,Never Say Never Againis a relatively compelling, reflective take on the legacy of what Connery did in the role.
Salem’s role inNever Say Never Againamounts to little more than a cameo, as she only really appears at the beginning of the story when she is setting up Bond on his next mission. With that being said, Salem does have a great repertoire with Connery, as she is there to remind him that he is no longer the young, agile spy that he used to be.

Never Say Never Again
4Caroline Bliss
Appeared in: ‘The Living Daylights’ (1987) and ‘License to Kill’ (1989)
Caroline Bliss was cast as Moneypenny during a transitional moment in the seriesin which the Bond franchisegrew slightly darker and grittier.The last fewRoger MoorefilmsOctopussyandA View To A Killhad become so campy and silly that they felt like parodies of the series, which inspired the Broccolis to take a darker direction whenTimothy Daltonwas cast as Bond inThe Living Daylights, and then reprised his role inLicense to Kill. These films are far closer in tone and style to the original source material, which unfortunately meant that Moneypenny’s role was seriously reduced.
Bliss sadly doesn’t have much to do in eitherThe Living DaylightsorLicense to Kill, as both films attempted to cut down on Bond’s flirtations with other women. Considering thatLicense to Killfocuses solely on a mission that Bond goes on that exists outside of his responsibilities at MI6, Moneypenny doesn’t really factor into the narrative at all. Perhaps Bliss would have gotten more opportunities to expand on the character had Dalton been able to make a third film in the series, but sadly she ended up getting replaced when the franchise went on an unprecedented six-year hiatus.

The Living Daylights
The Living Daylights: British secret agent James Bond is tasked with aiding a Soviet general’s defection to the West, but a complex web of deception soon leads him into a global conspiracy involving arms deals and assassinations. Amidst political intrigue and high-stakes espionage, Bond relies on his skills to unravel the truth.
3Samantha Bond
Appeared in: ‘Goldeneye’ (1995), ‘Tomorrow Never Dies’ (1997), ‘The World is Not Enough’ (1999), and ‘Die Another Day’ (2002)
Samantha Bond made her debut as Moneypenny inGoldeneye, and served asPierce Brosnan’s co-star throughout all four installments that he appeared in.Goldeneyewas a significant film withinthe history of the Bond franchisebecause it introducedJudi Denchas a new version of M, who actually gave Bond some criticism for his generally antiquated, sexist behavior surrounding women. Brosnan’s co-stars, such asHalle BerryinDie Another DayandMichelle YeohinTomorrow Never Dies, were actually far more empowered than previous films. As a result, Bond was able to expand upon her capacity as the character.
This version of Moneypenny was less reliant on Bond’s opinion, and actually developed a more playful dynamic with him. Brosnan was broadly one of the more comedic actors to play Bond, and as a result, there was more time for his version of the character to have chemistry with Moneypenny as he was receiving orders regarding his next set of assignments.

2Naomie Harris
Appeared in: ‘Skyfall’ (2012), ‘Spectre’ (2015), and ‘No Time To Die’ (2021)
Naomie Harris’ role as Moneypenny was revealed in a clever twist inSkyfall, which initially introduced her as an MI6 agent known as “Eve” who works alongsideDaniel Craig’s Bond. After suffering trauma following anincident in which Bond is nearly killed, Eve ultimately decides to retire from field work and help Mallory (Ralph Fiennes) transition into the new head of MI6 after the agency is under scrutiny by the British government. Although there are flirtations that she and Bond have, the films actually were able to go in a more progressive direction and depict the two as being simply friends. This became quite powerful in the subsequent films, as Moneypenny is one of the few people who has had the same experiences that Bond has, and thus can relate to the struggles that he experiences.
Harris was able to make Moneypenny into a compelling character before her identity was revealed, which speaks to the faith that the film’s writers had in her performance. While she began to resemble the classical version of Moneypenny who only existed within an office setting, Harris’ version of the character played a prominent role in bothSpectreandNo Time To Die, as she teamed up with Q (Ben Whishaw) to help rehabilitate Bond. One of the greatest strengths ofNo Time To Dieis that in addition to giving a definitive conclusion to Craig’s version of Bond, the film also paid off the development that characters like Moneypenny had received. Whoever inherits the role next will certainly have a lot to live up to in comparison to Harris’ performance.
1Lois Maxwell
Appeared in: 11 James Bond movies
Lois Maxwell was the longest serving Moneypenny in the Bond franchise, as she appeared in eleven Bond films, starting withDr. Nowas back in 1962. It was evident based on the trajectory of the series that the Broccolis recognized what a unique talent Maxwell was, as she was gradually given more to do in the subsequent films.Regardless of how outlandishthe films got, Maxwell was always there to give a snarky remark about the entire situation.
Maxwell was able to evolve her version of MoneypennywhenRoger Mooretook over the role, as she held a more maternal role as his frequent mentor. Although the idea of real continuity existing between entries in the series didn’t really come into fruition until much later on, Maxwell was able to make references to Bond’s previous adventures in a way that reflected the passage of time. Her consistency in the role is certainly of note; regardless of whether it was a genuine classic likeGoldfingerorOn Her Majesty’s Secret Service, or a complete disaster likeDiamonds Are ForeverorA View To A Kill, Maxwell delivered on the material that she was given. The Bond franchise has been reinvented for many generations, each of whom have their favorite 007 actor. That being said, Maxwell will always be the one true Moneypenny in the eyes of most longtime supporters of the series.
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