Fan-Cast: James Bond, part 3: Miss Moneypenny

“Flattery will get you nowhere… but don’t stop trying.”  — Miss Moneypenny, Dr. No

As promised, I continue fan-casting James Bond’s closest associates this week with the ever-loyal Miss Moneypenny.

Miss Moneypenny

Moneypenny is the private secretary and assistant to “M”, head of MI-6, and holds the rank of Lieutenant in the Royal Navy (actually, the Women’s Royal Naval Service until it was integrated into the Royal Navy in 1993). The latest version even did a bit of fieldwork before deciding she was better suited to administrative duties. As with “M”, the character’s creation appears to have been inspired by a mix of various real-life acquaintances/associates of creator Ian Fleming — from Kathleen Pettigrew (personal assistant to Stewart Menzies, the actual head of MI-6 from 1939-1952) to Joan Howe (Fleming’s own secretary at The Times in the 1950s, who typed the original Casino Royale manuscript).

The Four (Primary) Moneypennys

Moneypenny is incredibly attracted to — perhaps I should say infatuated/smitten with? — the dashing and roguish Agent 007, often daydreaming about marrying him or, at the very least, enjoying an illicit tryst. Knowing that this will likely never happen, she has (mostly) resigned herself to playful flirting with Bond. She is smart, efficient, and quite loyal.

Lois Maxwell played the role for all Connery and Moore films, as well as Lazenby’s one film. (The only exception was 1983’s non-official Never Say Never Again, in which Pamela Salem filled in.) Caroline Bliss was Dalton’s Moneypenny in 1987 and 1989, with the conveniently-named Samantha Bond taking over for Brosnan’s run. Craig’s first two films had no Moneypenny, but Naomie Harris has had the role since 2012’s Skyfall, which also gave her the first name “Eve”. I am not aware of any physical description given for the character, but the movie versions have obviously varied a bit. What does seem fairly consistent is that she is slim, attractive, and her age is roughly that of Bond, give or take. Over the years, the actresses ranged in age from mid-30s to late-50s, as did the Bond actors (though Moore was a bit older).

For the next reboot, I’d like to see Bond and Moneypenny continue to be about the same age: early- to mid-30s, though a slightly older Moneypenny would be OK. I would also like to keep a bit of sexual tension and Moneypenny’s unrequited feelings, which were barely there in Fleming’s original novels but have become identified with the character in the movies and later novels. To that end, attractive 30-something actresses are naturally my focus here.

Let me begin by saying that there are a couple Americans who I considered: Alison Brie (5’3″,b.1982) and Emma Stone (5’6″,b.1988). They would each bring different qualities to the role, and I thought they might do a good job. Assuming we want to stick with someone from the UK, though, I considered Emma Watson (5’5″,b.1990). However, she may be a bit too young (barely 30 by the time a reboot might shoot), and I’m not sure how well she’d fit the role. On the other hand, I thought Hayley Atwell (5’7″,b.1982) would be a fun choice. The reason I ultimately rejected her is that I’d rather see her as a “Bond girl”, in particular as an agent of some sort, so she can show off her “Agent Carter” moves.

Which brings me to my three preferred candidates for Miss Moneypenny…

Sienna Miller (Photo by Carlos Alvarez/Getty Images)

First choice: Sienna Miller (5’5″,b.1981). You might remember her from “Keen Eddie”, Layer Cake (w/ Daniel Craig), Stardust, G.I. Joe: The Rise of Cobra, American Sniper, or the recent The Lost City of Z. The British-American former model seems to have the right mix of prettiness and spunkiness (like Harris) that makes for a fun and interesting Moneypenny.

Keira Knightley

Next up: Miller’s close friend (and co-star in The Edge of Love), Keira Knightley (5’7″,b.1985). If you somehow don’t remember, Knightley has appeared in Star Wars: Episode I – The Phantom Menace, The Hole, several Pirates of the Caribbean films, King Arthur, The Jacket, Domino, Jack Ryan: Shadow Recruit, Everest, etc. Like Miller, Knightley is a very attractive and talented actress who could have a lot of fun with this relatively small, supporting role.

Honeysuckle Weeks

My third choice is less known, a tad older, and more “cute” than “pretty”, IMO. Honeysuckle Weeks (5’7″,b.1979) came to my attention as the driver/aide to Detective Foyle in “Foyle’s War”, so this casting would be especially appropriate(?) if Michael Kitchen (who played Foyle) became the next M. She was also in various British mysteries, as well as Red Mercury, “The Bill”, The Wicker Tree, “Inspector Lewis”, and “The Five”. I can definitely see her as Moneypenny.

That about does it. Have ideas of your own for Moneypenny? Let us know in the comments! I think I’ll take a break for now, but I’ll take a stab at fan-casting ‘Q’ and Felix Leiter in the coming weeks/months.

* All ideas copyright Christopher Harris, 2013-2017.

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