I'd like to understand the derivation of the phrase "oldest X in the book." Was this referring to a particular book, or was it an idiom that developed without a particular object in mind?
If it is just an idiom, how old is the idiom, and how did it develop?
Good question. It is an idiom: "They committed every crime in the book"; "He was always one step ahead of me, as he seems to know every trick in the book."; "He used every trick in the book to get her to sign the contract."
See every trick in the book on Wiktionary.
'The book' appears to be a metaphor for the body of knowledge. Compare: by the book, 'according to the correct or established form' (originally could have referred to the Bible).
'to play by the book' (strictly according to the rules of the game):
Edgar Allan Poe, Murders in Rue Morgue, 1845:
"To have a retentive memory, and to proceed by 'the book', are points commonly regarded as the sum total of good playing."
There's no literal "The Book", but rather a metaphorical "the book you got it from". Joke books are indeed a thing that exists. Here's one I used to own as a kid.
Jokes generally have prestige based on how original they are. If a person has heard a joke several times before, they aren't going to find it nearly as funny.
If you made it up yourself, that's clearly original. Someone who isn't that clever would be forced to get their jokes from a jokebook like perhaps the one I linked above.
So basically this is a way of denigrating the humor of someone who just told a joke. You are implying they are so unfunny that, not only did they have to get their humor "canned" from a book, but they don't even know enough to avoid jokes their audience is likely to have heard before.
