Top Ten Musicians Who Embody Cool

America has produced some very cool things: jazz, rock, blues, country, hot rods, Hammond organs, and electric guitars. Another one of the coolest things is the language itself, brewed in the melting pot that is America. Like jazz, blues, and rock, American English itself can't be imagined without the influence of African Americans. "Hep," "hip," "funky," "groovin,'" and "cool" are words I had assumed were coined by the early jazz musicians; however, as I dug a little deeper it seems likely that "cool" goes back even further.

You will find some very interesting reading if you search the Web for the origins of "cool." A 2013 article from Slate titled "The Birth of Cool" cites an article entitled "Negro English" in an obscure German academic journal (Anglia), written by a professor at Washington and Lee University in 1884: "Among the many 'Negroisms' that Harrison cites is the interjection 'Dat's cool!,' which is given without definition or explanation, and so we're left to wonder at how closely its meaning mirrors the modern." The reason may well be that the meaning of "Dat's cool!" in the 19th century was every bit as varied as it is today. The LA Times also ran an interesting piece in 2012 on "What Defines Cool?" They reported on a university study "Coolness: An Empirical Investigation" which actually tried to answer the question. In the end, "The researchers concluded that while coolness isn't necessarily easy to define, people recognize it when they see it." In English we've adopted some French words that seem somewhat related to what we think of as "cool." Debonair—attractive, confident, and carefully dressed (especially of men.) Suave—having a pleasant and charming manner that may not be sincere (especially of men.)

It seems cool is indeed similar to debonair and suave, because it too is especially associated with men. My approach in coming up with this list was simply to write down a list of musicians who spontaneously popped into my mind in relation to the concept of cool, and then narrow the list down to ten. When I finished I was struck that I only had a few women on my initial list, even after giving it some additional thought. How could that be? Early female jazz singers sang about "cool cats," and male rock singers sang about "hot chicks." There's no denying it, in popular culture women are often thought of as the opposite of cool, they are labeled as "hot."

There is another inherent flaw in coming up with such a list. We've all heard the expressions, "Never meet your heroes," and "Familiarity breeds contempt." So a public persona is not necessarily anything like the actual person. Another limitation is that "cool" is sometimes fleeting. For example, Chet Baker was the absolute embodiment of cool at the beginning of his career. With that in mind I selected musicians who retained their cool over decades.

1. Miles Davis

He came across as aloof and emotionally detached, but at the same time he was decidedly flamboyant in his tastes and style; in fact, he was enamored with rock stars such as Jimi Hendrix and Prince. In terms of fashion he was anything but static: elegant preppy, tastefully tailored suits, Hendrixesque-psychedelic, all the way to Michael Jackson outfits. Search the Web for his cars and among others you find a bright yellow Ferrari Testarossa, a lime green Lamborghini Miura S, and a bright red Ferrari 275 GTB. Above all else he was hands down the coolest musician in terms of music itself. In an age that worshiped at the altar of electric guitar, his trumpet managed to define cool. Bebop, cool jazz, hard bop, electric, funk, rock—he was always in the moment and never looked back.

2. Jimi Hendrix

The most iconic musician of the flower power, peace & love generation. Soft spoken off stage, outrageously provocative on stage, extraordinary in the studio, and one of the most influential electric guitarist of all time.

3. Elvis Presley

He was so cool that even Col. Parker's movie and recording deals couldn't ruin his career. Goolge "Elvis Presley" and you get about 29,700,000 results in (0,90 seconds!) Come on, you've got to admit that he had to be extremely cool to pull off those jumpsuits.

4. Frank Sinatra

From being the idol of fainting bobby soxers in the 40s big band era to the leader of the 1960s Rat Pack, in his day he was surely one extraordinarily cool cat. A singer who was admired by his peers and commercially successful, who went on to win an Academy Award as an actor. Even at the height of the British Invasion in the 1960s, he had some huge hits: "Strangers in the Night," "That's Life," "Something Stupid," and "My Way."

5. Willie Nelson

Today at age 83 this beloved country outlaw, singer, songwriter, actor, and activist remains unquestionably cool.

6. Johnny Cash

Another cool country outlaw loved by Nashville, who is also an enduring counter culture hero.

7. Burt Bacharach

There's a reason Mike Myers put Burt Bacharach in his "Austin Powers" films. He was driving in his car when he heard "The Look of Love" and wondered to himself, where have all the swingers gone? That was the genesis of the character Austin Powers.

Although he wrote and produced pop hits, he wasn't part of the youth counter culture in the 1960s. He was simply Burt Bacharach —dating and marrying glamorous actresses, doing TV specials, and writing hit records and great film scores in his own unique and unmistakable style.

8. Dizzy Gillespie

In his autobiography Burt Bacharach recounted going to jazz clubs in New York City as a young man. One night he approached a club, and there was the great Dizzy standing nonchalantly outside taking a break with a monkey perched on his shoulder. That was pure Dizzy, always outrageous, and in his own inimitable way, unquestionably cool. He even ran for president in 1964 and vowed to put Miles Davis in charge of the C.I.A. (Skip forward to 9:30 in the video clip for the section on Dizzy.)

9. Billy Gibbons

Super cool cars, guitars, threads, and an old testament beard. Not the most famous blues rock guitarist, but for me, after Hendrix the coolest.

10. Ray Charles

From his autobiography: "Then there were motorcycles. I learned to ride one in Tallahassee when I was about 14 or 15. I got to know the town pretty well, and soon I felt confident about riding round. Tallahassee was full of hills, and I loved racing up and down 'em, sometimes trailing my friend or riding next to him, so I could hear the sound of the exhaust and make sure to follow closely and yet not too closely. I know it sounds strange—a blind teenager buzzin' round on a motorcycle—but I liked that; that was me. I had always been nervy, and I always had a lot of faith in my ability not to break my neck." What else is left to say, he was cool beyond belief on so many levels.



Here are the others from my initial list: Prince, David Bowie, Louis Armstrong, Marvin Gaye, Duke Ellington, Bob Marley, Bruce Springsteen, Bob Dylan, Esperanza Spalding, Tal Wilkenfeld, Mick Jagger, Keith Richards, and Jeff Beck. If I had included groups The Beatles would have easily topped my list. So that's my list, and I'm sure some obvious choices must have escaped me. I hope you will give a shout out to your picks in the comment section.

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