Hancock started his career with trumpet player Donald Byrd's group. He recorded his first solo album Takin' Off for Blue Note Records in 1962. "Watermelon Man" (from Takin' Off) was to provide Mongo Santamaría with a hit single, but more importantly for Hancock, Takin' Off caught the attention of Miles Davis, who was at that time assembling a new band. Hancock was introduced to Davis by the young drummer Tony Williams, a member of the new band.

Hancock received considerable attention when, in May 1963, he joined Davis's Second Great Quintet. Davis personally sought out Hancock, whom he saw as one of the most promising talents in jazz. The rhythm section Davis organized was young but effective, comprising bassist Ron Carter, 17-year-old drummer Williams, and Hancock on piano. After George Coleman and Sam Rivers each took a turn at the saxophone spot, the quintet gelled with Wayne Shorter on tenor saxophone. This quintet is often regarded as one of the finest jazz ensembles yet. While in Davis's band, Hancock also found time to record dozens of sessions for the Blue Note label, both under his own name and as a sideman with other musicians Hancock also recorded several less well-known but still critically acclaimed albums with larger ensembles - My Point of View (1963), Speak Like a Child (1968) and The Prisoner (1969), albums which featured flugelhorn, alto flute and bass trombone in addition to the traditional jazz instrumentation. 1963's Inventions and Dimensions was an album of almost entirely improvised music, teaming Hancock with bassist Paul Chambers and two Latin percussionists, Willie Bobo and Osvaldo "Chihuahua" Martinez. During this period, Hancock also composed the score to Michelangelo Antonioni's film Blowup (1966), the first of many film soundtracks he recorded in his career. As well as feature film soundtracks, Hancock recorded a number of musical themes used on American television commercials for such then well-known products as Pillsbury's Space Food Sticks, Standard Oil, Tab Diet Cola, and Virginia Slims cigarettes. Hancock also wrote, arranged and conducted a spy-type theme for a series of F. William Free commercials for Silva Thins cigarettes. Hancock liked it so much he wished to record it as a song but the ad agency would not let him. He rewrote the harmony, tempo and tone and recorded the piece as the track "He Who Lives in Fear" from The Prisoner (1969). Davis had begun incorporating elements of rock and popular music into his recordings by the end of Hancock's tenure with the band. Despite some initial reluctance, pianist Hancock began doubling on electric keyboards, including the Fender Rhodes electric piano at Davis's insistence. Hancock adapted quickly to the new electronic keyboard instruments, which proved to be important in his future artistic endeavors. Under the pretext that he had returned late from a honeymoon in Brazil, Hancock was dismissed from Davis's band. In the summer of 1968 Hancock formed his own sextet. However, although Davis soon disbanded his quintet to search for a new sound, Hancock, despite his departure from the working band, continued to appear on Davis's records for the next few years. Appearances included In a Silent Way, A Tribute to Jack Johnson and On the Corner. Hancock left Blue Note in 1969, signing with Warner Bros. Records. In 1969, Hancock composed the soundtrack for Bill Cosby's animated prime-time television special Hey, Hey, Hey, It's Fat Albert. Music from the soundtrack was later included on Fat Albert Rotunda (1969), an R&B-inspired album with strong jazz overtones. Hancock became fascinated with electronic musical instruments. Together with the profound influence of Davis's Bitches Brew (1970), this fascination culminated in a series of album in which electronic instruments were coupled with acoustic instruments. This compilation is culled from those 1960s albums and singles.