Billed as learning from the masters (ostensibly in a subject you are trying to master), I find Masterclass more interesting as evidence of what sorts of people become masters of their craft + I use it to help me build out models of people who I admire enough to make part of my...shoulder brigade?
(For a number of them, I think they saw it as maybe a way to share their story/what they’ve learned about life, more than just their job; it’s a bit like they’ve done portraits of the people rather than their subject.)
I’d start with David Sedaris, then maybe Ken Burns (he’s way more epic than I suspected). I also enjoyed Frank Gehry, the architect, and appreciated his views on the value of a person creating something that’s uniquely them. Malcolm Gladwell is a great storyteller, but I’m a little uneasy about the focus of his values (maybe I have a similar issue with David Sedaris though? And it makes sense that masters would sort of be obsessed with their craft).
Many others are interesting without being “my people” Annie Leibovitz, Jimmy Chin, Bob Iger, Doris Kearns Goodwin, etc.
(Annual subscription is ~$100 and they periodically have a "give one, get one" deal for e.g. Christmas or Father's Day or whatevs. As of the fall of 2023, select classes are also free to borrow through Hoopla with a public library card.)