An original member of the Jazz Messengers, he later played in Horace Silver‘s quintet and freelanced with Gene Ammons, Kenny Burrell, Donald Byrd, Art Farmer, Jackie McLean, Hank Mobley, Lee Morgan, Sonny Rollins, and Phil Woods among others.
Some of Watkins’ best-known work can be heard when as a 22-year-old he appeared on the 1956 album, Saxophone Colossus by tenor saxophonist Sonny Rollins, with Max Roach and Tommy Flanagan. From that session, the tunes “Blue Seven” and “St. Thomas,” especially, have become revered not only as evidence of Rollins’ original genius but as fine examples of Watkins’ work.
According to Horace Silver‘s autobiography, Let’s Get to the Nitty Gritty, Watkins, along with Silver, later left Art Blakey’s Jazz Messengers because the other members of the band at the time (Kenny Dorham, Hank Mobley and Blakey) had serious drug problems, whereas Watkins and Silver were tired of being harassed and searched by the police every time they went to a gig in a new city and club.