Written By: Ben Cosgrove

When LIFE photographer Robert W. Kelley shot a few rolls of film at an intimate jazz gig on May 14, 1958, evidently neither he nor the magazine’s editors were jumping out of their skins with excitement.

Kelley provided scant notes describing the evening: just the date, the city and the subject’s name, “Miles Davis,” scrawled on the small archival file of the resulting photos. Why the pictures which capture the great, groundbreaking trumpeter, then just 31 years old, leading his band in an unnamed New York venue never made it into print remains a mystery to this day. [NOTE: A comment below cites research that places Davis and his band at New York’s Cafe Bohemia on that night. Ed.]

At this pivotal moment in his career, Davis was cementing a new iteration of his sextet, with John Coltrane, drummer Jimmy Cobb, bassist Paul Chambers, alto saxophonist Julian “Cannonball” Adderley and pianist Bill Evans. Less than two weeks after these pictures were made, that astonishing lineup would begin recording 1958 Miles, and by the following March they were at work on the best-selling and arguably the single most influential jazz album of all time: Kind of Blue.

Even artists outside of jazz rockers like Duane Allman and Pink Floyd’s Richard Wright, for example have cited Kind of Blue as inspiration. Davis’ friend Quincy Jones, meanwhile, has said: “I play Kind of Blue every day. It’s my orange juice.”

Maybe Kelley’s 1958 photos never ran in LIFE because seeing and hearing jazz greats on any given night felt so commonplace in New York at the time—the music mecca Birdland, after all, was just around the corner from the Time-Life Building. Maybe pictures of a groundbreaking young master of the art weren’t something to get worked up about.

But six decades later, when Miles Davis’ star shines brighter than ever and he’s acknowledged as one of the genuine titans of 20th century music, it’s hard not to get excited by the opportunity to see previously unpublished pictures of the man and the rest of his legendary sextet.

Unpublished picture of Miles Davis in New York, 958

Miles Davis plays with his sextet in New York City, 1958.

Robert W. Kelley Time & Life Pictures/Shutterstock

Miles Davis and John Coltrane play in New York City in 1958

Miles Davis (right) plays his trumpet beside a promising talent he’d recruited for his sextet in 1955, a man who’d go on to become a jazz giant in his own right: tenor saxophonist John Coltrane. Not long before this photo was taken, Coltrane had rejoined Davis’ group after a sojourn away with Thelonious Monk.

Robert W. Kelley Time & Life Pictures/Shutterstock

Miles Davis plays with his sextet in New York in 1958.

Miles hangs back while drummer Jimmy Cobb and bassist Paul Chambers (out of frame) play. It was only May of 1958, but the year was shaping up to be a busy one for Davis: Weeks earlier he had finished recording Milestones, a classic work signaling new stylistic directions, and by July he’d begin the sessions for the Porgy and Bess soundtrack.

Robert W. Kelley Time & Life Pictures/Shutterstock

Miles Davis takes a break from performing at a club in New York, 1958.

Miles Davis in New York, 1958

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of Miles Davis, close-up, in color, 1958.

For a 1958 TIME magazine profile, Davis explained the birth of his playing style, beginning with a local instructor in his hometown of East St. Louis, Ill.: ” ‘Play without any vibrato,’ he used to tell us. ‘You’re gonna get old anyway and start shaking.’ That’s how I tried to play — fast and light and no vibrato.”

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of Miles Davis and his trumpet, 1958

Miles Davis adjusts the mouthpiece of his trumpet at a New York club in 1958. He famously paid as much attention to what notes he did not play as to those he did. “I always listen to what I can leave out,” he once said.

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of Miles Davis in 1958

As he became more successful, Davis’ reputation as snappish and disrespectful of his audience — he was famous for turning his back to the crowd — became legend, earning him the nickname “The Prince of Darkness.” But his friends said Miles was sometimes misunderstood. Remembering Miles in 1991, Herbie Hancock explained to People magazine that Davis was not shunning his fans in concert, he was merely focusing on the music and his band.

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of Miles Davis playing his trumpet in New York, 1958

Miles Davis, 1958.

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of Miles Davis and Paul Chambers, 1958

Davis had a gift for seeking out the best talent on any instrument. In 1955, he recruited bassist Paul Chambers, just 20 years old but already a virtuoso, influential player.

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of jazz drummer Jimmy Cobb

Drummer Jimmy Cobb

Robert W. Kelley Time & Life Pictures/Shutterstock

Picture of Miles Davis in a New York nightclub in 1958

Miles Davis in a New York nightclub in 1958

Robert W. Kelley Time & Life Pictures/Shutterstock

Miles Davis plays in a nightclub in New York

Even after the mighty transformation of his own style in 1958, Miles Davis continued to switch things up, experimenting in later years with fusion, funk and rock. “I have to change,” he once said. “It’s like a curse.”

Robert W. Kelley Time & Life Pictures/Shutterstock

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