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Jane Moneypenny or better known as Miss Moneypenny is M's secretary, 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 and Quantum Of Solace.

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. Originally, Maxwell was offered either Moneypenny or introductory Bond Girl Sylvia Trench for her role in Dr. No. When she found out that the role of Trench had a scene where she wore nothing but a pajama shirt, she decided to go with the role that she defined in the series. Tragically, Lois passed away in 2007. 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. 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 flirtations. She has been friends with her successor in the role of Miss Moneypenny, Samantha Bond, ever since they both were eleven years old. Casting director Debbie McWilliams was unaware of this when replacing Bliss with Bond. Not expecting to return after the departure of Timothy Dalton anyway, Caroline harbored no ill feelings towards her friend, saying: "I am just glad it has gone to someone I love and who needs the money!".

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, though she used Q's virtual reality glasses, in Die Another Day. She has been friends with Caroline Bliss since both of them were eleven years old.

Best lines:

• "Flattery will get you nowhere... but don't stop trying. "- Lois Maxwell in Dr.No
• "You never take me to dinner looking like this James. You never take me to dinner period."- Lois Maxwell in Dr.No
• "Oh! The only gold I know of is the kind you wear, you know? On the third finger of your left hand."-Lois Maxwell in Goldfinger

• M: (on intercom) Miss Moneypenny. Give 007 the password we've agreed with Japanese SIS.
  Moneypenny: Yes, sir. We tried to think of something that you wouldn't forget.
  Bond: Yes?
  Moneypenny: I... love... you. Repeat it please, to make sure you get it.
  Bond: Don't worry, I get it. Sayonara. (You only live twice)

• Bond: Anything you want me to bring you from Holland, Moneypenny?
Moneypenny: A diamond...in a ring.
Bond: Would you settle for a tulip? [He drives away]
Moneypenny: [Longingly] Yes! (Diamonds are Forever)

• "My problem is, James you never do anything with me."- Lois Maxwell in On Her Majestys Secret Sevice
• "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
• "Someday you'll have to make good on your innuendos." -Samantha Bond in GoldenEye
  
• "You always were a 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 has yet to appear in a Craig film.

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