Weinstock was known for having artists record with almost no rehearsal time, recording large quantities of music from the jazz groups in New York City for Prestige and later its Bluesville, Moodsville, Par, Swingville and Tru-Sound imprints. He would have musicians record on one take, insisting that the additional takes were less spontaneous and that recording engineer Rudy Van Gelder did not need extra takes to adjust balance, and would reuse tapes if he thought that another take was needed. This left very few alternative versions of Prestige recordings. John Lewis and his Modern Jazz Quartet were one of the few able to overcome Weinstock's no-rehearsal practice, for the 1955 release of Concorde and for the 1956 album Django. Sonny Rollins and John Coltrane recorded the album Tenor Madness in 1956, with a saxophone duet that marked the only known recording of the two artists together.
Columbia Records had signed a recording deal with Miles Davis in 1955, but Davis still owed Prestige Records four albums in addition to Miles: The New Miles Davis Quintet, recorded in November 1955 after Davis had already started recording for Columbia. Weinstock had the Miles Davis Quintet record without retakes for two full days at Van Gelder's original recording studio in Hackensack, New Jersey, one in May and one in October 1956, building up a mass of material that was ultimately used to create four separate albums titled Cookin' with The Miles Davis Quintet, Relaxin' with The Miles Davis Quintet, Workin' with The Miles Davis Quintet and Steamin' with The Miles Davis Quintet. These were released over several years, and all achieved critical success. In his autobiography, Davis described the "great music we made at both those sessions" and said that he was "real proud of it", but that he was glad to have fulfilled his obligations to Prestige and was "ready to move on".
Within a few years of the label's establishment, Weinstock was hiring A&R; scouts to bring in and develop talent, and had started the transition to soul jazz with artists such as Charles Earland, Richard "Groove" Holmes and Willis Jackson. Over the years, Weinstock oversaw releases from such artists as Gene Ammons, John Coltrane, Eric Dolphy, Red Garland, Coleman Hawkins, Thelonious Monk, Sonny Rollins and Annie Ross. With as many as 75 recording sessions a year in the 1950s, Prestige released more than 1,000 recordings during Weinstock's 23 years of ownership.
In the mid-1960s, Weinstock relocated Prestige's head office to Bergenfield, New Jersey, just a few miles from his home in Tenafly, New Jersey. He would often prefer to have meetings in his home, feeling that he had more privacy there than at the office.
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