Originally comprised of two eponymous stories, later editions of the book added two others.
- "Octopussy": A crime from the past of a former major in the British army catches up to him.
- "The Property of a Lady": Top spy for the Soviets must be identified during an Auction for a Fabergé egg.
- "The Living Daylights": Bond must protect a defector from East Berlin with a sniper rifle.
- "007 in New York": Bond is tasked to warn a girl in MI-6's payroll of her double agent boyfriend.
In the movie side of things, the first story was incorporated into the backstory of the thirteenth James Bond film, with a hint of the second story as well. The first story's backstory of Bond being raised by a Swiss ski instructor was also incorporated in film twenty-four. The third story was grafted onto the beginning of the fifteenth film. A character name, Solange, from story no. 4 was used in Casino Royale (2006), and its plot inspired the finale of Quantum of Solace.
- Driven to Suicide: After their marriage went completely sour, Smythe's wife killed herself by overdosing on sleeping pills. Dexter Smythe himself is also in process of doing the same, albeit by the more slower path of drinking himself to death.
- Everything's Squishier with Cephalopods: An octopus that Smythe has nicknamed "Pussy" resides in the area that he owns. He is fascinated by it, and after he is fatally stung by a scorpion fish, decides to try his experiment of feeding it. They end up "shaking hands", and he dies.
- Hollywood Density: Subverted. Smythe carried a briefcase containing gold to bypass customs. He took amphetamines to be able to lift it easily enough to conceal its weight.
- It's Personal: Bond took the job of finding Smythe because the man he killed was a Parental Substitute for him in the past.
- Leave Behind a Pistol: Bond tells Smythe that he has a week before the authorities will apprehend him. He comes to realization that Bond is giving him a chance to kill himself, thus keeping things tidier for the paperwork.
- Nazi Gold: During World War II, Major Smythe learned about a stash of two Nazis' gold bars, and shot the mountain climber that helped him in the back of the head because of them. He's been living off of them since.
"The Property of a Lady":
- Feed the Mole: The money from the auction is going for a mole within MI-6, whom they are feeding with false information whenever necessary.
- Rule of Drama: When Bond hears that nobody in England does "going, going, gone" bit in auctioning anymore to provide a chance for last-second bidders, he finds it pitiful, since he thinks that it "adds to the drama".
"The Living Daylights":
- I Need a Freaking Drink: Bond calms his nerves with a glass of whiskey. When his spotter protests, he notifies that he's not the one who is supposed to kill someone.
- Senseless Violins: Bond suspects that Trigger brought her gun to the opera house in her cello case.
- Title Drop: The story ends with Bond quipping about scaring the living daylights out of "Trigger".
- Wouldn't Hit a Girl: When Bond sees through his scope that "Trigger" is the woman he has become fond of during the assignment, he chooses to shoot her Kalashnikov instead of killing her.
"007 in New York":
- Big Applesauce: The entire story is pretty much a description of places in New York from Bond's point of view.