The Sky Below is guitarist Miles Okazaki's sequel to his critically-acclaimed Trickster (Pi 2017), which the New York Times labeled "tenacious futurism" and Pitchfork called "obviously complex, the work of virtuosi." The album received critics' picks in both Downbeat and JazzTimes, acclaimed as "an intellectually hefty album that feels weightless" and "a real breakthrough." The Sky Below continues the story of Trickster, this time following the classical arc of an oceanic voyage, where the character travels across a boundary ("Rise and Shine"), enters the unknown ("Dog Star"), visits magical islands ("Anthemoessa" and "Seven Sisters"), is caught in a storm ("Monstropolous"), abandoned ("The Castaway"), and finds a way home ("The Lighthouse"). For these songs, Okazaki took each of the compositions from Trickster, reduced them to their basic components, and rewrote new compositions from this genetic material to maintain their symbolic and sonic continuity.

The Trickster band is comprised of Okazaki on guitar, Anthony Tidd on electric bass, Sean Rickman on drums, with the addition of Matt Mitchell on piano. A first-call musician on the cutting edge of jazz, Mitchell also prominently features Okazaki on his latest release, Phalanx Ambassadors (Pi 2019). The team of Tidd and Rickman, whom Okazaki first played with as the rhythm section of saxophonist Steve Coleman's Five Elements, form a seamless rhythmic foundation for the band. Together, they demonstrate the ability that they have honed for decades of negotiating abstract musical information while maintaining an unstoppable rhythmic drive. With it's narrative structure and Okazaki's judicious use of studio effects, The Sky Below evokes the fathomless depths of the sea, both familiar and strange.