M’s efficient, love-starved secretary, one of 007’s most ardent admirers, portrayed solidly by Canadian actress Lois Maxwell in the first fourteen James Bond films from Eon Productions. Caroline Bliss took over the role in The Living Daylights and Licence to Kill. She was then followed by Samantha Bond in the four Pierce Brosnan Bonds—GoldenEye, Tomorrow Never Dies, The World Is Not Enough, and Die Another Day. Most recently, Naomie Harris has played her in the Daniel Craig Bond movies Skyfall, Spectre, and No Time to Die. Barbara Bouchet portrayed Moneypenny’s daughter in the 1967 Casino Royale spoof, and Pamela Salem played Moneypenny in Never Say Never Again.

Starting with her introduction in Dr. No in 1962, Moneypenny’s blatantly sexual repartee with Bond before and after a briefing with M became a staple of the series. Like M and Q, her character was less comedic in the early films, as was her relationship with Bond, and the most recent Moneypenny has returned to that more serious tone. This version, portrayed by Harris and given a full name for the first time—Eve Moneypenny—starts as a field agent who nearly kills Bond in an abortive mission in Skyfall. She soon becomes one of his most trusted allies.