The cool factor- who has it?

Jim Morrison and the Doors, Bonnie Raitt,Greg Allman,David Bowie, Dave Mason,Roger McGuinn,Cher, Dean Martin, Tony Bennett,  Aretha Franklin, Ray Charles,Tom Jones....Rock and Pop...

Lester Young was "cool"  and one of those who use this adjective...Chet Baker was  refered as "the Prince of cool" by contrast  but at this time this was a jazz adjective linked to black musicians.

https://forum.audiogon.com/posts/2822510

50's, 60's or 70's Elvis, he practically invented R&R cool.

Contemporary cool - Leon Bridges, Son Little, Jaten Collin Dimsdale (Teddy Swims) Black Pumas, The Roots and Quest Love, Joss Stone, lots of truly cool people out there today making music. 

Lots of votes for Miles. Not surprising. Many other artists mentioned here whom I hadn’t heard of. I will try them. I think Joe Cocker (listen to St. James Infirmary ), Jimi Hendrix was cool. Later SRV. Chet Baker, for sure. Les Paul I would add. I would add Sade, Bonnie Raitt, and Natalie Merchant.  But then who can forget the J Geils Band and the Sensational Alex Harvey Band! Block of ice cool.