In 1959 Montgomery was signed to the Riverside Records label, and remained there until late 1963, just before the company went bankrupt. The recordings made during this period are widely considered by fans and jazz historians to be Montgomery's best and most influential. Two sessions in January 1960 yielded the record, The Incredible Jazz Guitar of Wes Montgomery, which was recorded as a quartet with pianist Tommy Flanagan, bassist Percy Heath and drummer Albert Tootie Heath. The album featured two of Montgomery's best known compositions, Four on Six and West Coast Blues. This album is included on the first volume of this two x four CD series, The Complete Recordings 1958 - 1960. Was Montgomery received many awards and accolades throughout his career; he was nominated for two Grammy Awards for Bumpin' in 1965 and received a Grammy for Goin' Out of My Head as Best Instrumental Jazz Performance by Large Group or Soloist with Large Group, in 1966. He was nominated again for his version of The Beatles' Eleanor Rigby and the LP Down Here on the Ground in 1968, and posthumously for Willow, Weep for Me in '69. His second album, The Incredible Jazz Guitar of Wes Montgomery, earned him Down Beat magazine's 'New Star' award in 1960. In addition, he won the Down Beat Critic's Poll award for best Jazz guitarist in 1960, '61, '62,'63, '66, and '67. Jazz purists relish Montgomery's recordings up through 1965, and sometimes complain that he abandoned hard-bop for pop jazz toward the end of his career, although it is arguable that he gained a wider audience for his earlier work with his soft jazz from 1965-1968. During this late period he would occasionally turn out original material alongside jazzy orchestral arrangements of pop songs. In sum, this late period earned him considerable wealth and created a platform for a new audience to hear his earlier recordings.