Keys moved to Los Angeles in 1970. In 1971, he signed to Gene Page's fledgling Black Jazz label and cut his debut album, the now legendary Shawn-Neeq. He gigged on his own before auditioning for the Ray Charles Orchestra.Keys' unique phrasing and his ability to balance sophisticated jazz harmonics with tough R&B and soul grooves were showcased nightly in the Charles band. In 1973, Black Jazz released Keys' second offering, Proceed with Caution. He toured briefly before being snapped up by Ahmad Jamal. Keys spent the next seven years with the pianist, recording six albums and touring the globe.
By 1975, Keys had relocated to the San Francisco Bay Area, where he became -- and remains -- an avid participant in its jazz community. He worked in live settings and recording sessions with John Handy, Bobby Hutcherson, Eddie Marshall, Leon Williams, Bob Braye, Ed Kelly, Eddie Duran, Bruce Forman, Junius Simmons, and Eddie Moore. In 1976, he played on Doug and Jean Carn's Ovation album Higher Ground. The 1980s proved similarly fruitful; Keys was an in-demand studio and live sideman, with credits including appearances with Tony Bennett, Pharoah Sanders, and Sonny Stitt. Keys began recording another solo album in 1984. In 1985, Olive Branch Records released tracks from these sessions as the album entitled Full Court Press; it was followed a year later by Maria's First.Keys continued playing sessions and performing with touring acts in the Bay Area and the occasional Los Angeles gig. In 1991 he was part of the band that recorded film composer James Newton Howard's original score for the film Dying Young. Working with his own trio, Keys released Standard Keys on Lifeforce Records in 1992; his session and live work continued at a relentless pace, which eventually took its toll. Some of his work included reuniting with Jamal for the pianist's 1994 album Night Song for Motown's MoJazz imprint, and a tour of Europe that resulted in Jamal's Live in Paris 1996. An Evening with Calvin Keys, taken from a radio broadcast, was released that same year.
He was sidelined in 1997 by heart surgery, undergoing a quadruple bypass. Undaunted, he released the widely acclaimed Detours into Unconscious Rhythms on Wide Hive Records. The large cast included organist Chester Thompson (Ray Charles, Santana) and upright bassist Kenneth Nash (from Jamal's band). After the album's release, Keys toured regionally in the U.S. and in Europe before returning to the Bay Area, where he performed with organists Big John Patton and Dr. Lonnie Smith, and Taj Mahal. In 2005 Keys recorded Calvinesque for Silverado. The album hit number 30 on the jazz charts.
His second Wide Hive release, Vertical Clearance, was issued in 2006. It reunited Keys with Doug Carn, and included Phil Ranelin, Sonny Fortune, Roger Glenn, and Babatunde in its lineup. In 2007 Keys released Hand-Made Portrait on Silverado, and received a tribute from fellow Midwesterner -- and fan -- Pat Metheny, who composed and included the tune "Calvin’s Keys" on his album Day Trip.Keys appeared on Ranelin's Living a New Day for Wide Hive and on organist Gloria Coleman's Sweet Missy for Doodlin in 2009. In 2012 Tompkins Square Records re-released Shaw-Neeq exclusively on 180-gram vinyl. Keys supported it by touring with a band, performing the album in its entirety. AMG.
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