The absolute poster child for this is 'Lazarillo de Tormes'. That anonymous 1554 novella is the blueprint, honestly. It's all Lazarillo's first-person account of serving a procession of increasingly awful masters, a starving nobleman obsessed with status but not eating, a priest hoarding communion bread. The kid's just trying to survive, and his sly tricks to get food or avoid beatings make you cheer for him, even when he's being dishonest. It’s not a grand heroic quest; it’s a scrabble for crumbs in a brutal, hypocritical society. The ending is the real kicker, though—his ultimate ‘success’ is a bitter, compromised deal with corruption that makes you question the whole system. I think its shadow is longer than a lot of people realize; you can see its DNA in everything from 'Moll Flanders' to 'Huckleberry Finn'.
That said, 'The Adventures of Augie March' by Saul Bellow deserves a nod. It’s a 20th-century American take, where Augie drifts through Depression-era Chicago trying on different lives, conning and being conned, never quite committing. It’s more philosophical and less grim than 'Lazarillo', but the core is the same: a rogue bouncing off a flawed world, refusing to be categorized.