Jimmy Cobb, prolific jazz drummer who worked with Bille Holiday, Dinah Washington, Dizzy Gillespie and most famously Miles Davis, as the last surviving member of Miles Davis’ First Great Sextet, has died at the age of 91. He fought a lengthy battle with lung cancer, and he is survived by his wife and two daughters.

Cobb’s subtle, steady and understated drumming style was the pulse of Miles Davis’ classic 1959 album Kind of Blue. “Jimmy, you know what to do,” Davis told Cobb before the session. “Just make it sound like it’s floating.” Kind of Blue was recorded shortly after Cobb’s 30th birthday. He was paid about $100 for all the album’s session, and never received any royalties.

For nearly three decades he was the last surviving member of Miles Davis’ First Great Sextet, serving to mentor young musicians and introduce generations of jazz fans to the sound of 1950’s hard bop.

“As a drummer, he makes you feel so comfortable,” guitarist Peter Bernstein—one of Cobb’s former students—said in the liner notes for This I Dig Of You, released last year. “Like, this is what it’s supposed to feel like.” As well as his decades long career as a band member and freelance musician, Cobb also taught classes at Stanford University, University of Greensboro and San Francisco State University.

Earlier this year in January, his daughter Serena created a GoFundMe page to raise money for his medical expenses. “Mentally and spiritually my father is as youthful and energetic as ever,” Serena wrote at the time. “But for the past 2 years he’s been dealing with some medical issues that have been causing severe challenges for him physically.”

She went on to explain that at the time he needed a full time caregiver as they chose holistic care which required “100% out of pocket coverage for both treatment and visits, as it isn’t covered by insurance.”