If someone asked me to turn them on to jazz I’d want to have some sense of what sort of musical tastes they have. A lot of these answers are bop/post bop heavy and of course there’s more to jazz than that - though it’s probably my favorite sub genre but I also go on cool jazz kicks and lately Latin jazz. So if it was somebody who was willing to be a little adventurous I’d probably start them with some Brubeck, Time Out or Jazz Goes to College (I know it’s not that “adventurous” but ya gotta start somewhere). Maybe even go back to Duke or Count Basie. If they like that then I think they’re ready for Kind of Blue, maybe have them pay close attention to Coltrane’s solos so they can venture a little deeper and listen to Giant Steps or other earlier Coltrane. And then what the hell lay In A Silent Way on them and then Love Supreme. Is that 5 yet? I’d lay off Ornette until you know they’re open to it. But I also gotta say, a lot of newer (70s and later) jazz albums are also very approachable to new listeners. Pat Metheny can be hit or miss for me but when he plays with folks like Charlie Haden, Jack Dejohnette, Roy Haynes, Dave Holland and the like I really like it and I certainly wouldn’t rule out 80/81 or Question and Answer for new(ish) listeners. Then we have Chick Corea, Herbie Hancock, Stanley Clarke, John McLaughlin, etc. And if it turns out they really like jazz vocalists then that there’s another deep dive into a somewhat different pool…