100%. I worked with an old-timer Newfoundlander who delighted in telling me that in the ought-sorties when he was a teen he passed out in a dinghy on the dock after a night of drinking and woke up at sea as an accidental stow-away on some merchant ship. He hid as long as he could but eventually got caught and it was some ship/crew from the eastern hemisphere and (to hear him tell it) threatened him with going overboard unless he got to work in the galley so that’s what he did. He said he sailed with them all over the world for two or three years before landing in Canada again and decided to take a stroll around his former community to learn that his family had assumed him dead, had the whole funeral or whatever, case closed in their minds. I asked him if he looked up his people to let them know and he was like fuck that shit I hated all of them with a passion! so he went back out to sea and did that most of his life. He was hilarious.
Jaimie Johnson who filmed the documentary Born Rich (and its sequel) pissed off enough of his family and peers that he was almost thrown out of high society for exposing its underbelly. He also lives a pretty normal life echewing his family fortune which is pretty dope. Might be along the lines of what you’re looking for. Good films either way.
ETA check out The One Percent as well, his follow-up from the first film.