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Herbie would go on to compose a number of songs with Blue Note that would either become standards in their own right (“Maiden Voyage”), staples of his live catalogue through his many evolutions (“Toys”), and foundations of hits for other artists (Us3’s “Cantaloop (Flip Fantasia)” reached the Top Ten in 1992 with a sample of “Cantaloupe Island”). Santamaria would join Herbie’s band for Inventions and Dimensions the shuffling “Succotash” is practically a salsa. The song’s subtle shading in the spaces between bebop, soul jazz, and R&B made it an almost-instant classic, and Cuban musician Mongo Santamaria’s version would become such a big hit, Herbie was able to live off of the royalties for years, giving him even more space for creative freedom.

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He based the rhythm of “Watermelon Man,” from his Blue Note debut Takin’ Off, on the sound of the produce delivery cart that rolled through his Chicago neighborhood the melody mirrors the calls of the driver shouting out what he had for sale. The label would provide a stable home for him as a solo artist and bandleader and allowed him to develop his style as a performer and composer. In 1962, while he was still a member of Byrd’s band, Herbie was signed by Blue Note Records. “I played things that were almost blasphemous and sounded grotesque,” he once said, “but they had a certain beauty that we could feel even if nobody in the audience could.” His time with Dolphy offered Herbie a glimpse of the harmonic complexity he’d soon become drawn to. He’d also perform on a pair of legendary sessions, for Freddie Hubbard’s Hub-Tones, where he takes a solo on the title track, and Roland Kirk’s Domino while Herbie’s playing didn’t make the final cut of Kirk’s album, you can hear him lean into the blues on an outtake version of “Termini’s Corner.” He’d even hook up with Eric Dolphy for a time, his cubist chords giving the saxophonist and flautist stable ground from which to take flight. “It’s a Beautiful Evening,” from Out of This World, shows him playing a supporting role, laying a beautiful harmonic bed for Byrd’s stirring solo – though his own solo hints at the commanding bandleader he’d become. He would play with Byrd from 1960 until 1963, giving him not only his first full-time gig, but also his first dates in a recording studio.

He worked with several well-known musicians, including Coleman Hawkins, but when a snowstorm stranded the great trumpeter Donald Byrd’s pianist, Herbie got his first big break. In 1960, Herbie left Grinnell College in rural Iowa to return to his hometown of Chicago, where he was determined to make it as a jazz musician.