"He'll Never Buy A Drink Again After Doing That/Telling That Story"

Factual Questions
1

This is at least a minor trope in older Anglophone literature (think Wodehouse, or the mock-old Flashman): a character does something so impressive/heroic, or tells an anecdote so hilarious/impressive/outre, that it is said of him that “he’ll never need to buy his own drinks after that” or “he had dined out many a time on that story.”

Was this ever largely/literally true of doing some great feat or telling some rip-roaring yarn? It certainly doesn’t seem to me like anyone would be eager to buy me dinner just because I have a couple of fairly colorful adventures in my past that make for reasonably fun anecdotage. If it wasn’t viable to do that in the past, where did the trope come from? If it was viable, where did it go?

2

Well, I think it’s clear that the phrase is a bit a hyperbole. However, someone who did some sort of impressive feat would certainly be wined and dined, and people would be happy to pick up the check.

I can think of one clear example, though it was from the 1950s in the US instead of in the UK. Rocky Marciano, after he retired from boxing, never paid for dinners. He once scolded a friend of is for offering, saying, essentially, “They enjoy picking up the tab for me.”

3

It seems this guy has done quite well out of it.