Internal Affairs stands out as an impressive solo debut from one of rap’s most skilled—and underappreciated—technicians of all time. But it’s just as notable as a fascinating time capsule of the state of hip-hop at the end of one of its most consequential and dynamic decades. At the time of this record’s initial release in 1999, a fiercely underground, "independent as fuck" (to quote a young EL-P) backpack scene had sprung up in seeming opposition to the mainstream successes and excesses of Bad Boy Records’ so-called shiny-suit era. That scene was dominated by Rawkus Records, the NYC indie that in quick succession released proudly non-commercial formative music from then-unknowns Mos Def, Talib Kweli, and EL-P’s group Company Flow. So when Southside Queens’ Pharoahe Monch—who had dropped three highly conceptual cult favourite albums as half of the duo Organized Konfusion—signed with Rawkus in 1999, it felt like a natural match, a safe homecoming for an underground veteran. But Monch and Rawkus had more ambitious plans, as the seminal single “Simon Says” made immediately apparent. Built around a catchy-as-hell sample of the Godzilla theme, the song was an indie-rap-friendly club banger at a time when that juxtaposition seemed impossible. It debuted prominently on Funkmaster Flex’s Hot 97 radio show amid his signature bomb sound effects—rap’s most important commercial co-sign. Although the rest of Internal Affairs never reaches the riotous heights of “Simon Says”, it generally follows that song’s approach—an underground hero opening up the cypher a bit to the audiences rapidly coalescing around rap radio and mixtapes. “Hell” and “No Mercy” featured Canibus and M.O.P., peers who had their own brief dalliances with commercial acceptance; love song “The Light” has Monch flexing his melodic smarts and impassioned singing voice; “Right Here” and the caffeinated Busta Rhyme duet “The Next Shit” wouldn’t have sounded wildly out of place on a DJ Clue mixtape. And “Simon Says” gets a Funk Flex-friendly extended posse cut remix featuring Method Man, Redman, Busta Rhymes and others. In between are Easter eggs for the heads, such as “The Truth” with Common and Kweli and “God Send”, a reunion with Organized Konfusion bandmate Prince Po. Monch’s rhymes aren’t quite as mind-bogglingly dense as they were on Organized classics like “Bring It On”, but his ability to fit thoughtful lyrics into intricate and unexpected rhyme schemes and rhythms is still legitimately jaw-dropping. (Pro tip: Brace yourself for—or altogether skip—“Rape”, an extremely problematic extended metaphor that compares rapping ability to sexual assault.) Despite the bright spots on this album and other Rawkus releases, the graduation of Monch and his compatriots to commercial overground never came to be—at least not for New York rap. Southern acts like Cash Money’s Hot Boys made the big mainstream jump instead, while Rawkus’ output and relevance dropped sharply. At the same time, Bad Boy’s dominance waned, JAY-Z and Nas battled for respect, and Eminem blew up, helping erase the feeling of a split between commercial and non-commercial rap. Fittingly, Monch got caught up in label limbo and didn’t release another album until 2007, while Internal Affairs was ensnared in a court battle over that Godzilla sample on “Simon Says”, keeping the album off digital and streaming platforms until 2019. But decades later, his performance on Internal Affairs still comes off as virtuosic, and you can hear echoes of his labyrinthine rhyme patterns and deep metaphors in the bars of Kendrick Lamar, Logic and others.