A native of New York, Jai embarked on his global quest after stay at Reed College in Oregon, when he moved to the San Francisco Bay Area to study sarod and singing with Indian master musician Ali Akbar Khan. But it was traveling to India that awakened Jai to "a strange and unexpected sense of homecoming," and during an extended stay in Bengal, he was strongly influenced by the legendary Bauls, a people "affected by wind" whose indigenous music is unschooled by concert hall standards but disciplined by generations of tradition. Of the many instruments in his repertoire, Jai most often turns to the Bauls' sarod-like dotar as his vehicle for bridging the diverse cultures in his musical synthesis.

Between the release of his widely acclaimed Footprints, which featured jazz trumpeter Don Cherry, and Monkey, Jai Uttal organized a seven-member band to perform his music in concert. The septet, which includes Peter Apfelbaum and several members of his Hieroglyphics Ensemble, appeared at the 1992 Montreux Jazz Festival.

While Monkey retains Jai's hallmark innovations of melding sampled and sequenced sounds with "real-time" instruments (including harmonium, gubgubbi, tabla, bansuri, cornet, saxophone, guitar, accordion, mandolin, and drums), it also radiates with the energy of collective interplay between Jai and Peter Apfelbaum, Will Bernard, Peck Allmond, Geoffrey Gordon, Daniel Paul Karp, Bruce Linde, Rob Vlack, Charlie Burnham, and others.