He subsequently performed with vocalist Dinah Washington, pianist Wynton Kelly, saxophonist Cannonball Adderley,[3][6] bassist Keter Betts,[7] Frank Wess,[8] Leo Parker, and Charlie Rouse.

He formed a trio with pianist Wynton Kelly and bassist Paul Chambers, both of whom were part of Davis' rhythm section.

The group toured and recorded as a trio, and also worked with Kenny Burrell, Wes Montgomery, Joe Henderson, J. J. Johnson and others.

[13] He played in a tribute band called "4 Generations of Miles", together with Ron Carter (bass), Mike Stern (guitar), and George Coleman (tenor saxophone).

[16] During his career, Cobb worked with Bill Evans,[13] Clark Terry, Stan Getz,[10] John Coltrane,[6] Wes Montgomery, Art Pepper, Wayne Shorter,[14] Benny Golson,[2] Gil Evans, Kenny Dorham, Frank Strozier, Bobby Timmons, Booker Little, Johnny Griffin, Akiko Tsuruga, Bertha Hope, Hamiet Bluiett, Nat Adderley, Mark Murphy, Jon Hendricks, Joe Henderson,[17] Fathead Newman,[18] Geri Allen,[19] Larry Willis, Walter Booker,[20][21] Red Garland,[22] Richie Cole,[9] Ernie Royal, Jerome Richardson, Jimmy Cleveland, Philly Joe Jones,[23] Sonny Stitt, Nancy Wilson, Ricky Ford,[8] Richard Wyands, John Webber, and Peter Bernstein,[24] among many others.

[2] Source:[27] With Cannonball Adderley With Nat Adderley With Lorez Alexandria With John Coltrane With Miles Davis With Ricky Ford With Benny Golson With Joe Henderson With Hank Jones With Wynton Kelly With Wes Montgomery With David "Fathead" Newman With Sonny Red With Shirley Scott With Bobby Timmons With Sarah Vaughan With others