Cobb, born in Washington D.C. in 1929, began his touring career with saxophonist Earl Bostic in 1950. This led to a cascading series of gigs with vocalist Dinah Washington, pianist Wynton Kelly, and saxophonist Cannonball Adderley.
His most famous work arrived at the end of that decade: Along with Davis’ modal, melodic masterpiece Kind of Blue — which Rolling Stone named the 12th-best album of all time — he joined the trumpeter on several other albums, including 1959’s Porgy and Bess, 1960’s Sketches of Spain, 1961’s Someday My Prince Will Come, and the 1962 live set Miles Davis at Carnegie Hall.
But Kind of Blue remains an unparalleled jazz landmark, and Cobb’s shimmering cymbal work and feather-light pulse helped the album achieve its otherworldly sense of cool.
“Miles would tell us all little things to do and then have us work off his idea,” Cobb told Billboard in 2019. “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.”
In the late Fifties, Cobb also played on Wayne Shorter’s debut LP, 1959’s Introducing Wayne Shorter, and a string of albums from John Coltrane, including his influential 1960 record Giant Steps (on the song “Naima”).
Cobb issued his first set as bandleader, So Nobody Else Can Hear, in 1983. He released his two final albums, This I Dig of You and Cobb’s Pocket, in 2019.