James Bond secretary Miss Moneypenny is an iconic part of the spy franchise, but Roger Moore outing Octopussy attempted to replace her with new character Penelope Smallbone. With the upcoming movie, No Time To Die, James Bond will celebrate his twenty-fifth onscreen outing. The secret agent’s illustrious screen career began with the late Sean Connery’s influential turn as Bond in 1962’s Dr. No, the same movie that introduced flirtatious secretary, Miss Moneypenny (Lois Maxwell).
An office confidante of Bond’s, Moneypenny has been ready with a quick-witted quip to answer his countless come-ons through her many screen iterations. To date, four actresses have played Miss Moneypenny over the years and, like gadget maker Q or MI6 Head M, she has proven a pivotal enough figure to appear even in Daniel Craig’s darker, post-Bourne Bond outings.
However, way back when Octopussy was released in 1983, Roger Moore’s second last Bond film considered replacing the iconic character with a younger alternative. Octopussy introduced Penelope Smallbone (Michaela Clavell) as the assistant to Lois Maxwell's Moneypenny, and although she didn’t have a sizable role, the introduction was intended to allow the character to smoothly replace Moneypenny in later outings. As stated by Octopussy director John Glen in the movie's commentary, the producers felt Maxwell might be approaching the end of her run in the role, so they decided to introduce a younger assistant who could become the new Moneypenny should the actress decide to leave.
However, Moore’s campy iteration of Bond didn’t have the same rapport with Moneypenny’s potential replacement, and Octopussy soon proved both the first and last appearance of the short-lived Penelope Smallbone. While the movie may set her up to be a potential recurring character, Smallbone evidently failed to make an impression with audiences, leading producers to recast Moneypenny when Maxwell exited the part. Maxwell returned for the next movie A View To A Kill in 1985, which was both her and Roger Moore's final Bond outing. She was briefly replaced by Caroline Bliss for two movies but alas - much like Bliss’ James Bond performer Timothy Dalton - her tenure was brief before she was replaced by Samantha Bond, and Dalton was replaced by Pierce Brosnan in 1995’s Goldeneye.
Miss Moneypenny has never gained another apprentice since Octopussy's Penelope Smallbone, although Skyfall did provide the character with a full name and backstory. As was the case with Bond himself, Skyfall saw the franchise attempt to flesh out the enigmatic Moneypenny and render her a more rounded character. The series has since made an admirable stab at fleshing out Naomie Harris' Moneypenny, although some franchise fans still prefer the more light-hearted banter of earlier James Bond and Miss Moneypenny iterations like the inimitable pairing of Moore and Maxwell.