Even in the thick of the bountiful early ’90s scene, the Queens-bred duo known as Organized Konfusion stood out. On their self-titled debut and their revered follow-up, 1994’s Stress: The Extinction Agenda, Pharoahe Monch and his partner, Prince Poetry, defined the lyrical vanguard with ear-bending enjambment, melodic cadences, stutter-stepping flows, and furious, multisyllabic rhyme flurries. Perhaps more than any of their contemporaries’, OK’s records conveyed an exhilarating sense of possibility: like the avatars of free jazz, they had the chops and the courage to take a song anywhere, at any time.

Conceptually, the group was just as adventurous, rhyming from the perspectives of stray bullets and “hypnotical” gases. The way they cloaked battle rhymes and social commentary in clouds of energetic abstraction marked them as heirs to legendary Bronx super-weirdos the Ultramagnetic MC’s—as well as forefathers to scores of unlistenable rappers who never mastered the proper ratio of organization to confusion.

Critical acclaim and $4.25 will buy you an iced mocha latte, so after a third album, 1997’s The Equinox, Monch decided to go it alone. The year 1999 saw the much-anticipated release of Internal Affairs on the tastemaking Rawkus Records. Like the disc with which it shared advertising space, Mos Def’s Black on Both Sides, Internal Affairs showcased the versatility of a newly solo artist with ambitions and influences that both transcended and embodied hip-hop. Monch crooned, sparred with a who’s-who of guest MCs, and spewed high-concept rhymefests in the OK vein.

But it was “Simon Says,” Monch’s attempt to simplify his flow for maximum commercial impact, that gave the MC’s MC a bona fide crossover hit. Over an ominous sample jacked from a Godzilla movie, it commanded dancers to “get the fuck up,” and they obeyed in droves. Club DJs loved the song; radio embraced it. Charlie’s Angels and Boiler Room picked it up for their sound tracks. Then the Tokyo-smashing monster (or his human representatives) sued for the uncleared sample, and Rawkus was forced to pull the album from stores.

It would be nearly eight years before Monch released his next long-player, Desire, in June 2007—two or three eternities in the notoriously fast-moving world of hip-hop. Few artists could have marshaled a fan base after such lag-time, but hip-hoppers of a certain era are proving to be quite elephantine in the memory department (see: the resurrected career of MF Doom), and Desire found an audience.

It didn’t hurt that the album showcased Monch at the height of his powers: pushing boundaries with conspiracy theories, multipart narratives, and Tom Jones impressions; challenging listeners to digest his wordplay at...