Who’s my favorite Bond girl? That’s easy. No contest. By a landslide. Eve Moneypenny.

That’s right. In a cinema world of Pussy Galore, Xenia Onnatop, Agent Goodhead and other Bond women with names created by men, Miss Moneypenny was beautiful, funny, dependable and could stand toe to toe with any incarnation of James Bond without having to have her clothes unshed. For years I have said that the arts, school and Miss Moneypenny will always be there for you.

Let’s stroll down memory lane, toss our hat onto the coat rack perfectly and take a seat at her desk without crumpling her papers.

Lois Maxwell (Dr. No to A View to a Kill)

For many Bond fans, Lois Maxwell is the one and only. Her stretch would cover Sean Connery, George Lazenby and Roger Moore. Like Desmond Llewellyn’s Q, Maxwell’s Moneypenny was that lovable to audiences that they kept bringing her back. Her chemistry with Connery was the best and at times more fiery than with some of the traditional Bond girls. This happens when one attends the Royal Academy of Dramatic Art in Canada (with classmate Moore) after serving in the Canadian Women’s Army Corps. Maxwell was not just an international model who looked pretty and for whom acting was secondary.

As an older guy, I am happy to see that Moneypenny saying “Flattery will get you nowhere, but don’t stop trying” with a gentle forehead smooch by Connery is a GIF. The same scene opens with Moneypenny smacking Bond’s hand. In real life, Connery would have decked a woman doing that (check out his Barbara Walters interview), but with Maxwell it was banter. Maxwell’s Moneypenny was an equal. She’s not a put-upon in the secretary pool. “You never take me to dinner looking like this. You never take me to dinner, period.”

As a young insecure lad, her moments meant a lot. Her attitude of “Hey, I am a catch, too!” was inspiring to someone who felt unnoticed by girls in the school hallways. With each film, I wanted to date her. Forget that superspy neanderthal, Moneypenny. You don’t know when he’s going to be back. I’ll have dinner waiting for you at home. I had these thoughts as a youth. The most vulnerable we saw Maxwell’s Moneypenny is not the wedding in On Her Majesty’s Secret Service (although that’s close, and her banter with Lazenby is also nice and light) but in her final banter with Connery in Diamonds Are Forever:

“What can I bring you back from Holland?”

“A diamond? In a ring?”

“Would you settle for a tulip?”


Apparently, Maxwell was tighter friends with Moore, but his Bond is more dismissive towards her, which was bit of a bummer for me. The biggest example was in Octopussy when producers attempted to introduce an assistant for Moneypenny named …Penelope Smallbone. Bond arrives with flowers, takes out one for Moneypenny and hands the rest to Smallbone. James Bond turned into Rod Stewart. To quote their moment in The Man with the Golden Gun

“Moneypenny, you’re better than a computer.” 

“In all sorts of ways.” 

Maxwell’s non-Bond work goes back to 1946. She won a Golden Globe for Most Promising Newcomer for her work in the 1947 Shirley Temple film That Hagen Girl. The same year she made her Bond debut in Dr. No, she was the nurse in Stanley Kubrick’s Lolita. A year later, she appeared in the Robert Wise film The Haunting. She also did quite a bit of telly when not at MI6.

Maxwell’s strangest credit was appearing in the 1967 spy film Operation Kid Brother starring Neil Connery, a cheap attempt to pass off Sean’s brother as the next action superstar. (Spoiler alert: It didn’t work.) The film also features Bernard Lee (the original M) and Adolfo Celi, who played Thunderball’s villain. Distributed by United Artists, the film was wonderfully mocked by Mystery Science Theatre 3000.

Post-Bond, Maxwell had seven credits, her final being the Jeremy Irons-Forest Whitaker film The Fourth Angel in 2001. Maxwell died in 2007. I still miss her.

Caroline Bliss (The Living Daylights and License to Kill)

Caroline Bliss could have easily been one of the traditional Bond women, but she wears glasses and her hair is up.

Thanks, Hollywood.

Among Bliss’s non-Bond work, her first screen credit was in 1982 playing Princess Diana in the TV film Charles & Diana: A Royal Love Story. She had a few film and television credits before getting her cinematic office job, and her final credit was in 1996.

Samantha Bond (Goldeneye to Die Another Day)

There’s no bantering while Pierce Brosnan sits on her desk, but Samantha Bond’s Moneypenny still gets her quips in from a distance.

“Hope you stay Onnatop of things.” – From Goldeneye. Nice touch.

Samantha Bond’s best moment was at the end of Die Another Day where she does what many would do if given the opportunity — use virtual technology to fool around with virtual James only to be interrupted by Q’s successor, R. (John Cleese).

The first television credit for Samantha Bond was in 1983. She also appeared in Erik the Viking as Helga. Samantha Bond was constantly working before and after her Moneypenny experience, most notably appearing in Downton Abbey as Lady Rosamund Painswick.

Naomie Harris (Skyfall to No Time to Die)

Story time: I got to attend a press screening of Skyfall weeks before it opened. (The film was number two in my top 10 for 2012). That year, I had spent many dad-daughter evenings watching several James Bond films (mostly Connery). Skyfall would be my daughter’s first Bond film in a proper cinema. One of my favorite moviegoing moments was watching my wife, Lynne, and daughter, Emma, watching Skyfall. Highlights included the opening action sequence, creepy-ass Javier Bardem and Emma’s face when we find out M’s (Judi Dench) first name was Emma. The final moment where my daughter’s face lit up huge was when Bond (Daniel Craig) says “We’ve never been formally introduced,” followed by Naomie Harris standing behind her famous desk and responding, “My name’s Eve. Eve Moneypenny.”

“I look forward to our time together, Miss Moneypenny.”

“Me, too. I’m sure we’ll have one or two close shaves.”

Much as Daniel Craig’s turn is the origin story of how Bond becomes 007, I loved the early chemistry and close shaves of Craig and Harris. Plus, that was a great character reveal of Harris. From then on, we saw them as contemporaries with Moneypenny getting to do plenty of non-desk work.

Résumé-wise, Harris has the best career of any Moneypenny — having also appeared in Michael Mann’s Miami Vice film, Rampage, the Pirates of the Caribbean franchise, Venom: Let There Be Carnage and more — and is showing no signs of slowing down. She received a Best Supporting Actress Oscar nomination for Moonlight in 2017.

If by some chance the brief rumors of Gillian Anderson being considered for Bond have a whiff of truth, here’s my résumé to play Mr. Moneypenny. My typing is better than my shorthand …

Matthew Socey is host of the podcast Film Soceyology for WFYI-90.1 FM in Indianapolis. This column is dedicated to Tafetta Vee.