The cool factor- who has it?

Giving the women their due. Julie London, Peggy Lee, Lana Del Rey. 

Mose Allison so cool and clever.

Louis Prima and Keely Smith, "just A Gigolo", their whole act was the epitome of cool. 

Dave Cousins of Strawbs, do people equate sensitive with cool, or is cool about being aloof? I do love the entire Brit folk/rock/traditional movement of early 70's. Brit music in general way cool, they've invented so many genres.

Michael Jackson

Elvis

Bob Seger

Prince

Frank Sinatra

Eric Clapton

Buddy Holly

@sns  ..."Miles Davis was not a cool guy in real life, many, many issues."

You are right. Great example how most questions / issues are so general as to offer lots of options for interpretation... @sns is right... without qualification... his personal life was a disaster. 

+1 @larsman 

In the jazz world, I'd include players who bring (or brought) out the best in others. Miles Davis would be cool by that measure, and so would Art Blakey, Ron Carter, Charles Lloyd, and Tommy Flanagan. I'm sure there are many more....

Ben Webster - Soulville