The Hunt for Red October/Funny

Novel

 * The fact that, in writing one of his books, Clancy (who did not know how a United States submarine worked) managed to accurately describe it and its features. He was then visited by the Navy, who had a few questions to ask...
 * What makes it even funnier is that he had extrapolated how it worked through simple library research. The Navy was in a panic over how this civilian had managed to obtain classified secrets, and these "secrets" were out there available for anyone smart enough to put all the pieces together, as long as they had a valid library card.

Movie
""When he reached the New World, Cortez burned his ships. As a result, his men were well motivated. More tea anyone?"
 * During the final shootout in the Red October's missile room, Alec Baldwin's perfect mimicry of Sean Connery saying "'Some things in here don't react too well to bullets.' Yeah, like me."
 * The revelation that Ryan speaks Russian when the Americans first board the Red October.
 * Ramius' calm explanation of why he ensured his superiors found out he was going to defect once he'd left;

[Everyone else looks horrified]."


 * He then proceeds to troll them even further by saying they should be afraid of the Soviet fleet... until they leave, when he tells Borodin alone not to worry because he knows the entire fleet, having trained many Soviet commanders, and has an advantage.
 * "Andre... you lost another submarine?"
 * This would have been even more amusing in the novel, as the Konovalov was the third sub the Soviets lost. (The Red October to barratry, and an attack sub named the ES Politovski to a reactor meltdown)
 * The Flight Engineer of the E-2C Hawkeye recalling a flight over the Sea of Japan where the turbulence caused even the pilot to throw up all over the cockpit and windshield, then elaborating on how it wasn't your typical puke, but 'huge industrial-sized chunks'. He's telling this to a green-looking Jack Ryan on an already horrifyingly turbulent flight while munching on a chocolate bar and offering it to Ryan.
 * Doubling up with a Crowning Moment of Awesome, when the USS Dallas comes blasting out of the water while evading the Konovalov's torpedo. The Russian sailors aboard the American frigate don't know that the Dallas is in fact helping the Red October, and instead deduce that their Badass captain had scared the Americans out of the water.
 * During the briefing with Jeffrey Pelt, Ryan realizes Ramius's motives, quietly muttering "You son of a bitch...", before repeating it loud enough for everyone to hear, making Pelt ask "You wish to add something to our discussion, Dr. Ryan?".