Miles Davis: A Leader of Leaders

Do I contradict myself? Very well, then, I contradict myself; I am large—I contain multitudes.

—Walt Whitman

A 20th-century icon with a protean musical legacy, Miles Davis was over six decades a stylistic shape-shifter akin to Picasso in the visual arts.

He followed his own artistic muse. Miles was never content with complacency.

From varieties of jazz in an acoustic vein from the mid-1940s to the mid-’60s, turning in the late-’60s through the end of his life in 1991 to electronic music fusing rock, pop, funk, and even elements from the soundscape of the German classical composer Karlheinz Stockhausen, Miles’ epitaph could have been Walt Whitman’s memorable lines: “I am large—I contain multitudes.”

Play with Miles, Become a Leader

Here’s a short list of musicians who became well-established leaders after tenures with Davis: John Coltrane, Cannonball Adderley, Bill Evans, Herbie Hancock, Ron Carter, Wayne Shorter, Tony Williams, Chick Corea, Keith Jarrett, and one of the foremost alto saxophonists on the scene today, Kenny Garrett.

Let’s gain some insight into how and why Miles became a leader of leaders.

Miles’s own path as a leader got a kickstart during his tenure with Charlie “Bird” Parker in the mid-1940s. Barely 20 years old, Miles’ spare melodic style was in development and greatly contrasted with the high-flying virtuosity and rhythmic genius of his idol Dizzy Gillespie, co-founder with Bird of the bebop style. Parker heard potential in Miles and liked how his style contrasted with his own. In terms of a leadership style, unlike Gillespie, Parker didn’t speak of music theory with Miles—you had to pick up what you could on the fly.

Charlie Parker and Miles Davis

This approach and intent turned out to be the same Miles employed a decade later with John Coltrane. In the mid-1950s Coltrane was searching for the fullness of his own sound and style. Miles dug the way Coltrane’s extroverted facility on tenor contrasted with his introspective trumpet style. Miles wasn’t a big explainer either—as Sonny Rollins has said, Miles knew what you could do and gave you space to grow.  And grow Coltrane did—after work with ensembles led by Miles and Thelonious Monk, ‘Trane became the most influential improviser in jazz after Parker.  

MIles’ leadership mastery was itself fully formed by the Kind of Blue modal period in 1958, resulting in the great Miles Davis Sextet—with Coltrane, Paul Chambers (bass), Cannonball Adderley (alto sax), Jimmy Cobb (drums), and Wynton Kelly (or Bill Evans) on piano. By then Miles had conquered an addiction to heroin and had been a leader in his own right for a decade, first collaborating with Gerry Mulligan, Gil Evans, Lee Konitz, et al., to launch the “cool style” in the late 1940s, then spearheading the “hard bop” style with Rollins, Coltrane, Red Garland, Chambers, and Philly Joe Jones in the early to mid-’50s. (‘Trane, Garland, Chambers, and Philly Joe were members of Miles’ first great quintet.)

If Miles had ceased forming groups after Kind of Blue—the best-selling jazz recording of all time—his impact on the evolution of jazz would have been secure. Yet he followed up by securing a second great quintet, with Herbie Hancock, Ron Carter, Tony Williams, and, eventually, Wayne Shorter, integrating elements of bebop and hard bop with their own take on the avant-garde, free-ish jazz experiments of the 1960s.

Now let’s get even deeper, via a few representative anecdotes and statements by Miles, to paint a leadership picture of his individual genius combined with the ensemble mindset ethos of jazz. Miles later ventured into other genres, striving for commercial relevance as jazz became less popular, so our focus here is on his last great jazz quintet.

Mistakes? What Mistakes?

Miles Davis once reportedly said, “Do not fear mistakes—there are none.”

In his own playing, he made imperfections sound beautiful. In Moving to Higher Ground: How Jazz Can Change Your Life, Wynton Marsalis writes that Davis “would release recordings with mistakes, and they still sound good. The imperfections give the music even more flavor and personality.”

Miles once explained to Clark Terry, his early idol from East St. Louis, that “When I’m playing, I like to miss.” Clark asked him why. “Because if I attempt to make something, and I miss it, it makes the people wonder what I would’ve made if I had made that.”

Dr. Billy Taylor recalled Miles saying that “a mistaken note is only one half-step from the right note,” a nice variation of another line attributed to him: “It’s not the note you play that’s the wrong note – it’s the note you play afterward that makes it right or wrong.”

Miles’ perspective on mistakes aligns with the non-linear attitude of creative leadership Jewel Kinch-Thomas outlined last week.

Once, when a young Herbie Hancock blazed the piano chair in Davis’ second great quintet, Herbie hit a clunker of a chord during a show. Davis was out front, taking a solo. Since the creative risk of creating the new in the now, at the speed of thought in front of a captivated audience, is always high, the risk of failure is ever-present.

It was a moment of truth and flow.

Rather than stopping mid-chorus, or staring at Hancock menacingly for his egregious faux pas, Davis, used to turbulence, surprise and the unexpected, paused, then played back the “incorrect” notes into the course of his solo, weaving a wrong into a lesson of right, keeping the music moving forward—straight ahead.

Here’s Herbie’s own telling of the tale.

Play What You Believe

Miles didn’t just say what he believed, he enacted it, played it, embodied it, jazz praxis style.

During an interview several years ago, Wayne Shorter gave me another angle on this dynamic. Wayne was riffing on the wisdom of grandparents who were more in touch with their inner identities than so many today. “Stop making a mountain out of a molehill” is a statement Wayne recalled hearing such elders say.

“Sometimes I would say a little something like this when speaking with Miles. And Miles would be in that same zone. We’d talk about this a little bit, with a kind of philosophical [edge], and he’d say, ‘Why don’t you play that?’ I said whoa. Miles was about that.”

Wayne Shorter, Ron Carter, Miles Davis, and Tony Williams

Ron and Herbie on Miles 

Grandmaster bassist Ron Carter engaged in a conversation with Herbie Hancock about their time with Miles for the book Miles Davis: The Compete Illustrated History.  

This brief excerpt, with emphasis added in bold, says volumes about Miles’ embodiment of creative, collaborative, shared, democratic leadership mastery, jazz style.  

Ron Carter: Every night with the Quintet felt like we were going to a laboratory. Miles was the head chemist and he would come out with these beakers full of liquid or powder, and it was our job to take these ingredients that he put on the table. His job was to keep up with us. 

Sometimes we didn’t do it right and sometimes he didn’t do it right, but that was the fun of it all. No one cared if you didn’t get the same reaction each night, or if you created an explosion, or somehow got the wrong results, we knew that tomorrow night was another chance to try to make something happen. 

Herbie Hancock: It was incredible that this great musician had the balls to let us go that far just because we chose to, and we felt totally comfortable making that kind of commitment professionally on the stage with Miles as our leader. But the Quintet was not your typical leader plus sidemen situation. Miles’ primary goal was to encourage all of us to contribute to the development of the sound of that band. 

Besides being the leader and the person with the overall vision, he was also one of the five musicians contributing to that evolution. 

Ron Carter: We were all equal partners . . .