Chester Sheard, photographer, was in a jazz bar when a raspy voice behind him asked about sax player John Coltrane.

“Are you the guy who took those pictures of ‘Trane?’ ”

“Yeah, I’m the guy,” Mr. Sheard said, turning to see it was Miles Davis, who seemed to re-invent jazz every time he picked up his trumpet.

With a reputation that might be described as challenging — Davis could be gruff, even turn his back on an audience — he’d been nicknamed the Prince of Darkness. Now, he faced Mr. Sheard. With his high forehead and impassive expression, Davis looked as majestic and mysterious as an Easter Island monolith.

Miles Davis, by Chester Sheard.

Miles Davis, as photographed by Chester Sheard.

Davis liked his Coltrane photos. So he let him stick around. And Mr. Sheard went ahead and took pictures of the man Duke Ellington dubbed the Picasso of music.

He shot at some of Chicago’s hottest nightclubs, like Bronzeville’s Club DeLisa and the Plugged Nickel in Old Town. Capturing a curled lip, a crabbed finger or a bead of sweat, his images conveyed urgency and passion.

In addition to Davis, Coltrane and Ellington, he photographed bluesmen Muddy Waters and Howlin’ Wolf and jazz artists Dizzy Gillespie, Ella Fitzgerald, Charles Mingus, Thelonious Monk, Herbie Hancock, Art Blakey, Alice Coltrane, Sun Ra, Joe Williams, Max Roach, Jimmy Garrison and Cassandra Wilson.

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Jimmy Garrison, as captured by Chester Sheard.

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His photo of B.B. King, face creased with concentration, became the cover of King’s “Live in Cook County Jail” album, a 1970 concert recording that captured “The Thrill is Gone” legend at the height of his power. The album was hailed by Rolling Stone as one of the 500 greatest LPs of all time.

“Sheard’s fantastic shot of B.B. King is iconic,” said Bobby Reed, editor of DownBeat magazine. “ ‘Live in Cook County Jail’ is certainly one of the most famous blues albums of all time. Everyone who’s a blues fan knows that image.”

Mr. Sheard’s portraits also were featured on Oscar Peterson’s “Blues Etude” and on the front and back of the Coltrane album “Infinity.”

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This image Chester Sheard shot of John Coltrane is on the cover of Coltrane’s album “Infinity.”

Mr. Sheard, 85, who lived in Chicago from the 1960s to the 1980s, died May 16 at his Milwaukee home.

In addition to the world of jazz, he also photographed scenes from the civil rights movement and draft-card burnings at anti-war protests in the 1960s. On one memorable occasion, a visit to a barbershop gave him the chance to photograph a legendary fighter in his prime — Muhammad Ali, then known as Cassius Clay.

“He used to get his hair cut in Woodlawn at 63rd and Greenwood, and he heard this boxer was in the gym next door,” said his son, Patrick Sheard. “He saw Muhammad Ali hitting the heavy bag, and the heavy bag just swinging and swinging. And [Mr. Sheard] said, ‘I tried to hit the heavy bag, and I couldn’t move it.’ ”

<small Photographer Chester Heard's image of Muhammad Ali.

An image of Muhammad Ali by photographer Chester Sheard.

Mr. Sheard rarely used a flash, preferring natural light. With quiet authority and ease, he’d glide through clubs as if he wore a cloak of invisibility. “I don’t have to get in the way to get a good shot,” he’d say.

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Miles Davis and Herbie Hancock, by Chester Sheard.

“He had a charisma that allowed him to get close to his subjects, where he could get the pictures of B.B. King or Miles Davis,” said his nephew, Craig Barker, “where you could actually see the sweat on their brow.”

Barker considered his uncle a father figure because his own dad, Mr. Sheard’s brother, died when he was about 2. His uncle “gave me a camera, and he said, ‘Capture the moment. It’s not about the pose,’ ” Barker said. “When you catch a person off-guard, you really catch them in that moment, like Miles Davis with his hand on his hip.”

Born and raised in Kenosha, Wisconsin, Mr. Sheard attended Bradford High School and studied photography at a community center.

He wrote stories and shot photos for Muhammad Speaks, a newspaper published by the Nation of Islam. Later, he worked for The Kenosha News and Milwaukee Sentinel. He sold images to Der Spiegel, DownBeat, Ebony, Jet, Metronome, Paris Match and Time, according to his son.

Beyond Chicago, he traveled to clubs in Philadelphia and New York to get pictures of jazz musicians.

Curator Michael Flanagan couldn’t believe it when he came across Mr. Sheard and his work at a farmers’ market at Beans & Barley on Milwaukee’s East Side. “It seemed like kind of a rare and wonderful thing,” Flanagan said, to find him amid “scones and potted plants and produce.”

“There’s Chester Sheard, with his black-and-white photos clothespinned to some string,” Flanagan said. “He was a sweet guy, completely willing to talk to you and talk about the pictures. There’s a picture of Miles Davis; there’s a picture of B.B. King. They were 20 dollars, and I was, ‘You gotta be kidding me.’ ’’

unnamed-2“He took great pictures,” said Flanagan, director of the Crossman Gallery at the University of Wisconsin-Whitewater and a board member and curator for Milwaukee’s Walker’s Point Center for the Arts, which exhibited some of Mr. Sheard’s photos.

“Mr. Sheard was a key photojournalist during the civil rights movement,” said Peter McConnell, co-contributor to the Jazz Stage page on Facebook. “His candid, up-close images of musical icons such as John Coltrane, Miles Davis, Duke Ellington, Ella Fitzgerald, Thelonious Monk and the recently departed B.B. King will live forever. He left us a priceless gift.”

Mr. Sheard liked golf and TV’s “Scandal.” And, “He would often say he played backgammon for blood,” his son said. He found peace through meditation and Buddhism.

Mr. Sheard admired Jay Z — especially when he rapped, “I’m not a businessman, I’m a business, man.”

He liked referring to himself as “the good brother Chester.”

A memorial is being planned.

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Ella Fitzgerald, by Chester Sheard.