James Bond might be the one who gets all the acclaim, but he’s not the only operative of Her/His Majesty’s Secret Service working hard to save the world from supervillains, you know. While it’s true that 007 is less of a team player on the whole than someone like Mission: Impossible‘s Ethan Hunt, he still has an array of allies who always have his back. Although there’s also his CIA buddy Felix Leiter and MI6 Chief of Staff Bill Tanner, the most iconic Bond supporting characters have to be M, Miss Moneypenny, and Q.
And just like Bond himself, these characters have been portrayed by various different actors over the past 60 years of Bond-dom. Similarly, matching the rising and falling tides of the franchise’s quality across the decades, some of the incarnations of these characters have been more well-received than others. Some made incalculable impacts on pop culture while others are hardly remembered by anyone outside hardcore 007 diehards.
So let’s step aside the worn-out arguments over which Bond actor is better than who, and instead rank every M, Miss Moneypenny, and Q there’s ever been in the official EON canon (unofficial entries like Never Say Never Again and 1967’s Casino Royale will not be included).
Miss Moneypenny (Caroline Bliss)
Appearances: The Living Daylights (1987), License to Kill (1989)
With apologies to Caroline Bliss, her 1980s incarnation of Miss Moneypenny is certainly the weakest M/Moneypenny/Q of the entire Bond franchise. It was never going to be easy to be the first to replace Lois Maxwell as M’s lovelorn secretary, but Bliss’ incarnation feels like a caricature of Moneypenny — complete with oversized glasses none of the others wear — and she has little to offer outside of insipid pining over Dalton’s 007.
M (Robert Brown)
Appearances: The Spy Who Loved Me (1977) [as Admiral Hargreaves], Octopussy (1983), A View to Kill (1985), The Living Daylights (1987), and License to Kill (1989)
After initially playing the supporting role of Admiral Hargreaves in The Spy Who Loved Me, Robert Brown was hired as the new M after original actor’s Bernard Lee passed away. Brown has the distinction of being the boss of both Roger Moore and Dalton’s Bonds, bringing a sterner, less avuncular energy to the part of the MI6 chief. His most notable moment comes when he fires 007 from the service in License to Kill.
Q (John Cleese)
Appearances: The World is Not Enough (1999) [as R], Die Another Day (2002)
Similar to Brown, John Cleese received an impromptu promotion once long-term series icon Desmond Llewellyn died. After initially appearing as Q’s clumsy assistant R in The World is Not Enough, Cleese got to be Q himself in Die Another Day. In this film, he’s much more authoritative and has a pronounced irritation with 007. Cleese would’ve been a decent Q if the series hadn’t been rebooted in the very next movie.
M (Ralph Fiennes)
Appearances: Skyfall (2012), Spectre (2015), No Time to Die (2021)
Ralph Fiennes had the near-impossible job of following Judi Dench as the new M, but he’s managed it with aplomb over the past three movies. While his M lacks the depth of the parental relationship Dench’s version shared with Craig’s Bond, the duo nonetheless have an interesting dynamic in which the levels of power between them constantly shift. Fiennes’ M is someone who respects Bond a great deal, even if they frequently butt heads.
Miss Moneypenny (Samantha Bond)
Appearances: GoldenEye (1995), Tomorrow Never Dies (1997), The World Is Not Enough (1999), Die Another Day (2002)
If Samantha Bond’s Moneypenny was continually portrayed as she is in her tremendous introductory scene in GoldenEye, she’d be much higher on this list. Unfortunately, although she starts out as a highly independent woman with a life outside of Bond and the office, she quickly devolves in future appearances until we get the terrible virtual reality love scene between her and Brosnan’s Bond in DAD that makes a mockery out of her character.
Miss Moneypenny (Naomie Harris)
Appearances: Skyfall (2012), Spectre (2015), No Time to Die (2021)
Naomie Harris has the honor of being both the most pro-active Moneypenny in the series’ history and for enjoying the benefit of being part of the franchise during its Mission: Impossible-aping years of bolstering the roles of the MI6 staff. As such, Harris is probably the most fleshed-out of all the Moneypennies (she even gets a first name — it’s Eve) and she shares a fiery and flirtatious chemistry with Craig.
M (Bernard Lee)
Appearances: Dr. No (1963) – Moonraker (1979) [11 films]
In a series that has often played fast and loose with its source material, Bernard Lee’s M feels like he walked straight out of the Ian Fleming novels, as his tough, no-nonsense and yet fatherly authority figure is an admirably close adaptation of Bond’s boss from the books. While we hardly got to know anything about his M as a person, Lee handled his endless expository scenes with a deft touch and made the formulaic debriefing scenes a treat.
Q (Ben Whishaw)
Appearances: Skyfall (2012), Spectre (2015), No Time to Die (2021)
Sorry, Fiennes and Harris, but the Craig era’s best reinvention of an MI6 mainstay is definitely Ben Whishaw’s Q. While Cleese’s iteration was essentially just a Llewellyn clone, Skyfall totally reimagined the tech whizz from the ground-up, depicting the third Q as a much younger computer genius. No Time To Die eventually revealed he was gay (in a moment that could’ve been better handled, but still), making him the franchise’s long-awaited first LGBTQIA+ main character.
Miss Moneypenny (Lois Maxwell)
Appearances: Dr. No (1963) – A View to a Kill (1985) [14 films]
Despite Harris’ many plus points, it’s hard not to rank the original Moneypenny highest, however. The character is a surprisingly minor part of the Ian Fleming novels, so it’s really all on Lois Maxwell for making Moneypenny the beloved cornerstone of the Bond world that she’s viewed as today. Maxwell got to work with Sean Connery, Roger Moore, and George Lazenby, although it’s certainly with Connery that she shares the most electrifying chemistry.
M (Judi Dench)
Appearances: GoldenEye (1995) – Spectre (2015) [8 films]
There’s just no beating Judi Dench as M. For starters, as a fixture throughout both the Brosnan and Craig eras, Dench was the only M an entire generation of Bond fans knew for many years, so she’s held in high regard. Aside from that, she also possesses the most layered, complex, and satisfying relationship with Bond, specifically Craig’s. Instead of just being his stern boss, Dench’s M is very much a surrogate mother figure for the orphan spy. She fully deserved the honor of being the first MI6-er to receive a proper finale in Skyfall.
Q (Desmond Llewellyn)
Appearances: From Russia With Love (1964) – The World is Not Enough (1999) [17 films]
As legendary as Dench is, Desmond Llewellyn can’t be shaken from the top spot thanks to both his unbeatably long stint in the franchise and the oodles of charm he brought to his role. Llewellyn’s Q scenes were always guaranteed to deliver the laughs and brighten up even the lesser entries in the series. Serving opposite every Bond from Connery to Brosnan, Llewellyn struck up wonderful chemistry with them all, although there’s a special, er, bond between the then-elderly Q and Pierce. Everybody now: “Pay attention, 007…”