Or I guess we could go noir with Miles...
For Miles I'd probably go with one of the one hour jams from the Agharta or Pangea live in Japan albums. He gets on stage, does whatever the hell that was for an hour or two in the most uncompromising manner imaginable; no 'hits', nothing familiar to the audience, no conscession to expectations whatsoever. Job done in the coolest possible way.
Arthur Conley: Sweet Soul Music
Just to make it clear, I'm sticking with The Ipcress File. The rest is just pontification.
Si Inspector.
For sheer 60s "groovieness", I'd have to go with this classic... Still one of my favourite Sci Fi films as well.
[YOUTUBE]https://www.youtube.com/watch?v=6jOis2GuKUk[/YOUTUBE]