As 'Kind of Blue' Turns 60, Drummer Jimmy Cobb Shares Miles Davis Memories

Miles Davis, Paul Chambers and Jimmy Cobb
Herb Snitzer/Michael Ochs Archives/Getty Images

Miles Davis performs onstage with his bass player Paul Chambers and drummer Jimmy Cobb at the Apollo Theater in 1960 in New York City.

When Billboard called up Jimmy Cobb, who at 90 has been the last surviving member of the sessions that created the 1959 jazz masterpiece Kind of Blue by Miles Davis since The Chief himself left us on Sept. 28, 1991, the evening news could be heard at a healthy volume in the background, clear enough to make out the phrase "Moscow Mitch" being uttered by the anchorman. When asked of his thoughts on the present situation between the two countries as opposed to what was going down 60 years ago when they were making Blue, Cobb admits the fog of memory got the best of him in that regard.

"Not to downplay its importance to history, but it's hard to remember at what time it happened," he admits.

However, when asked his thoughts on whether the cool sounds of the album may have been instrumental in calming the frayed nerves of a country in the recesses of a Cold War with the then-Soviet Union, he responded with an emphatic "I sure hope so!"

Cobb's mind may not have been on political science the night he spoke to Billboard about an album considered one of the greatest pieces of music ever made for its 60th anniversary. But at a very active 90, the drummer has plenty of stories and insight into a piece he once hailed as "made in heaven" -- and how it's played into a 70-year career that continues with the Aug. 16 release of his excellent new quartet album, This I Dig Of You.

Originally released on Aug. 17, 1959, Kind of Blue was the result of Miles Davis' burning desire to keep jazz on the forefront of creativity and innovation. But rather then ramping up the rhythms of the bebop era, the trumpet master and his Avengers-style team of ace players, which included Cobb, Cannonball Adderley and John Coltrane on saxophones, Bill Evans and Wynton Kelly on piano and bassist Paul Chambers, focused on the sounds between the strikes. The modes, as any knowing music theorist would call them, gave credence to the term modal jazz and paved a new road into the 1960s for the genre just like he had done a decade prior with his original 78rpm singles for Capitol Records.

"Miles Davis had a record date, and he usually had pretty good record days, and he was in contact with some people that were changing his thoughts on things, namely George Russell the composer," explains Cobb. "Russell had a book called the Lydian Chromatic Concept of Tonal Organization, and it had a lot of influence on the way the music was recorded for Kind of Blue. It was this combination of Russell, Bill Evans and Gil Evans—those three guys, and Miles of course, that had a lot to do with the direction his music was going in 1959."

Cobb also cites another huge influence setting the scene for Kind of Blue, that being the renowned pianist Ahmad Jamal, whose impression on the young trumpet player was instilled early on in his career.

"He listened to so much Ahmad Jamal," Cobb, who was a good personal friend of Miles, proclaimed. "In fact, when he was in Chicago, he would go to the hotel where Ahmad Jamal was playing like every night. And if you listen to some of his first recordings, it had a lot to do with what he heard from Ahmad, in terms of tuning and conceptualizing the music and all that, and also played a part in [what we were doing in 1959] too."

Kind of Blue has been analyzed, theorized, canonized and even demonized eight ways to Sunday by music theorists and jazz scholars the world over, so to rehash what makes the five songs comprising the original LP—"So What," "Freddie Freeloader," the Bill Evans-co-penned "Blue In Green," the 11-and-a-half-minute epic "All Blues" and the improvised gem "Flamenco Sketches"—so prevalent going into 2020 is peak redundancy. Yet regardless of whether you make it your morning orange juice like Quincy Jones told renowned Miles Davis expert Ashley Khan or are just coming into it as a new listener, there's always a new wrinkle to discover upon each listen.

"Miles always wanted to be different," states the drummer. "He was always looking for somewhere else to go. He always wanted to move forward, and never looked back on stuff. Kind of Blue was another step towards his goal, that's all really."

It's worth mentioning that Cobb was also pulling double duty at the time, working in Coltrane's own band as leader on such classic albums as Giant Steps and Coltrane Jazz for Atlantic Records two weeks after the recording of Kind of Blue and, in the case of the two alternate versions of the Coltrane Jazz highlight "Like Sonny," even during their time with Miles.

"They used to have a thing where Coltrane would go to New Jersey every Saturday," he explains. "He had some kind of commitment over there with Rudy Van Gelder, and this was back when Van Gelder was making records out of his mother's house. And I went out there with him on a couple of those Saturday appointments."

Luckily, all the members in the Kind of Blue ensemble were strategically recruited for the music he was composing on the album, thus making side trips to do other sessions more plausible so as not to cross the boss. The one player who did get burned in the process was pianist Wynton Kelly, who was by all accounts the main pianist of the group who recorded Kind of Blue but only appears on "Freddie Freeloader." Taking his place on the rest of the album was Bill Evans, largely because of the purpose he served in creating the sound Davis was looking to achieve and his role in the lineup from the '58 Miles compilation comprised of sessions with the sextet with Evans on piano.

"It was pretty tricky because Wynton was in the band at the time," Cobb recalls of the situation with Kelly. "So he came in when we had a record date, and he showed up and he looked over at the piano to see Billy and was wondering what the hell was going on. And I said to him, 'Be cool, everything's getting squeezed in on the date. Don't worry, ain't nothing happening.' That's what happened. He made it on one record, and he's in the history books on that record, 'Freddie Freeloader.' He made it on one side of the album, the blue side."

In fact, it was Wynton who Cobb goes furthest back with out of all the members of the Kind of Blue group.

"When I first went on the road, I went on the road with the Earl Bostic Big Band, and Dinah Washington was the featured attraction," he explains. "So when Dinah sang, she was accompanied by a piano player, and that piano player was Wynton Kelly. This was in 1950, and the bass player, his name was Keter Betts, and Wynton and I would play for Dinah as a trio."

By the time Cobb began playing drums for Davis on the second side of the trumpet player's 1958 LP Jazz Track, he knew he had some major shoes to fill by replacing Philly Joe Jones, drummer for the first Miles Davis Quintet who left the seat after Milestones. But thanks to the insight of some buddies, he knew what he was in for by taking the job.

"When Philly Joe Jones had left the group to start a band of his own, I had been sitting in with a couple of other drummers who were in Miles' band, like Art Taylor," he recalls. "Me and Art were friends. So that helped me to get to know the music of Miles Davis from the inside a little bit. Then I got to know Joe, because we used to hang a little bit, and he'd tell me what to do and not to do playing with Miles. But a lot of times some of those guys were doing stuff that I wasn't into doing. I stayed away from heroin and all that."

Still, Cobb cherishes numerous good memories of Miles outside the studio.

"I used to hang out at his house a lot," he remembers. "I'd drive up with him to the boxing gym, where he'd practice and spar with the other guys. And he always had the nicest cars, man… a couple of Ferraris and things like that, including this one convertible. We always had a good time."

The warmth you can hear in Cobb's voice as he reflects on his dear old friend is truly telltale of the synergy between the two men across the entirety of Kind of Blue. As a listener, it makes you rethink the entire way you hear the album when you put it strictly in the context of the duality between Cobb and Davis. But that's what makes Kind of Blue such an enduring, invincible and unshakable masterpiece for 60 years; it's an album whose timeless and forward-minded arrangements will continue to shape the way not only jazz music is performed but R&B, electronic, rock, pop, classical and even metal for generations to come. In his must-read autobiography, Miles wrote of how an early memory he had when he was six years old walking home down a dark road after church provided the root of his direction with Kind of Blue. But in looking at it through a different lens, perhaps it was the simple comfort of friendship that truly defines its perseverance as a piece of 20th century art.

"Miles would tell us all little things to do and then have us work off his idea," adds Cobb. "He trusted all of us because he knew we were all good musicians. He didn't really have to do anything else but say what he wanted done. One time he tried to tell me something about playing the drums with both hands, and I turned to him said, 'Um, let me play the drums!' But we were good friends, so I could say things like that to him without worrying about getting fired."