Riley contributed to an estimated 300 albums, including more than a dozen cut with tenor saxophonist Johnny Griffin between 1960 and ’62—most of them also featuring Griffin’s classic two-tenor hookup with saxophonist Eddie “Lockjaw” Davis. In 1962 he made waves via his work with Sonny Rollins on the canonical album The Bridge, the saxophonist’s first release following his historic sabbatical.

Riley’s association with Monk began in 1964 with the album It’s Monk’s Time, also featuring bassist Butch Warren and saxophonist Charlie Rouse. Riley also recorded with the pianist in ’64 for Monk. and Live at the It Club, and appears on 1966’s Straight, No Chaser and ’68’s Underground.