A few from the category, HUH WHAT THE HECK I DIDN’T KNOW THEY EVER MET:

Michael Jackson and George Harrison, Leonard Nimoy and Jimi Hendrix (with Noel Redding), Sammy Davis Jr. and Brigitte Bardot, Andy Warhol and Muhammad Ali, Arthur Conan Doyle and Harry Houdini.

All legendary figures. I just realized all except Brigitte Bardot have passed away.