Late night "Kind of Blue", low lights and a large Islay whisky is pretty much my idea of perfect fun.....KoB is really a pretty accessible jazz album. If you want to get extreme try, Miles' "*****es Brew" is it. Regarded as the recording that fired off electric jazz fusion.
But Miles....there was an obscure Australian movie made in the early 90s called 'Dingo'. It was about an outback postman who played jazz...and one day a plane landed and out stepped .....Miles Davis, the coolest man alive. Truly, a bizarre film, and I think Miles last film appearance. Look it up if you like Miles, it got some great music in it. Heres a clip....
Miles Davis - 'DINGO' (1991) - YouTube