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Jane Moneypenny or better known as Miss Moneypenny is M's secretary who is Bond's boss and the head of the British Secret Service. Although she always played a small part in the movies, her relationship with Bond was always highlighted which was completely nonexistent in Fleming's novels. Since she first appeared in 1962, the role of Miss Moneypenny has always been included in every Bond film with the exception of Casino Royale.

Actresses:

Lois Maxwell (appeared from Dr.No - A View to a Kill) Lois Maxwell was born Lois Hooker in Kitchener, Ontario on the 14th of February 1927. She was the first actress to portray Miss Moneypenny and boasts a total of 14 Bond films under her name. Many fans agree that Maxwell was the definitive Moneypenny. In the addition to the 14 Bond films, Maxwell also portrayed Moneypenny in a 1967 made-for-television special (produced by EON Productions) entitled, Welcome to Japan, Mr. Bond. This special is included in the 2006 special edition DVD release of You Only Live Twice. She also won a Golden Globe for "Best Newcomer" for her performance in the Shirley Temple comedy That Hagen Girl in 1947. Tragically, Lois passed away recently. Read more.

Caroline Bliss (appeared in The Living Daylights and Licence to Kill) Caroline Bliss is a British actress who replaced the longstanding Lois Maxwell for the role of Miss Moneypenny in the James Bond series. She was 26 when she first portrayed Moneypenny in The Living Daylights. She chose to wear glasses to distance herself from Maxwell's Moneypenny. She returned as Moneypenny in Dalton's second movie Licence to Kill though her role seemed more like a cameo. Probably due to limits in the script, Bliss' Moneypenny lost the charm of Maxwell's Moneypenny with almost no banter with Bond and with him ignoring her subtle filrtations.

Samantha Bond (appeared in GoldenEye - Die Another Day) The ironically named Samantha Bond replaced Caroline Bliss for the role of Miss Moneypenny in GoldenEye. Many fans of the Bond/ Moneypenny tandem say that no other couple portrayed the relationship between 007 and Moneypenny as well as Brosnan and Bond. In an interview with BBC 4, she said that along with Brosnan departing from the role of 007, she will also retire from the role of Moneypenny. Although a short lived Moneypenny, she does have one claim to fame: she's the only Moneypenny who kissed Bond instead of him kissing her (Moneypenny's fantasy kiss scene in Die Another Day).

Best lines:

• "Flattery will get you nowhere... but don't stop trying. "- Lois Maxwell in Dr.No
• "I didn't know you were a music lover. Any time you want to come over and hear my Barry Manilow collection..."- Caroline Bliss in The Living Daylights
• "You always were the cunning linguist James."- Samantha Bond in Tomorrow Never Dies
• The role of Miss Moneypenny wasn't included in Casino Royale although there was a probable reference to her character.
  • Vesper: I'm the MONEY.
  • Bond: Every PENNY of it.
  Moneypenny won't be in Craig's next outing but will be in Bond 23.