When an artist’s career has spanned several decades, it’s easy for some of the stylistic landmarks to be forgotten. In the case of Jay-Z, the GOAT contender has come to be defined by a collection of classics. Reasonable Doubt. The Blueprint. The Black Album. Some might even cite American Gangster among the prestigious lot. The reverence toward Hov’s finest works has established them as essential projects within the hip-hop canon, ammunition for those citing his cultural dominance. 

And rightfully so. Each of the aforementioned has found Jay undertaking and mastering different styles and concepts. His debut arrived as a mafioso masterpiece. Blueprint found him exploring new sonic territory, taking to soul samples alongside Just Blaze and Kanye West. The Black Album found Jay enlisting his favorite producers, resulting in a different voice on every track (while Neptunes and Ye landed a pair apiece). American Gangster was a full-blown concept album, lyrically dense and inspired by the Denzel Washington film. For the younger fan keen to discover the core of Jay’s catalog, it’s likely those projects are heralded as musts. Yet in the late nineties, Jay went on an interesting run that hardly sparks contemporary discussion. At the center of said run stood Vol. 2...Hard Knock Life, winner of the 1999 Grammy Award for Best Rap Album.

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Though it may have been a minute since you’ve heard the project in full, you probably remember one of its singles. A roster that includes “Money Cash Hoes” with fellow nineties juggernaut DMX, the Jaz-O-assisted “N***a What N***a Who,” the Annie-evoking titular track, “Can I Get A…” with Amil and Ja Rule. “Money Ain’t A Thang.” The list goes on, though the cuts tend to get deeper. Still, those active during the late nineties New York boon look fondly back on Vol 2, though it certainly marked a vast stylistic departure for the traditionalist Jay. The year prior, Hov dropped off Vol 1, which felt like a natural successor to Reasonable Doubt. When his follow-up landed on September 29th, 1998 Hard Knock Life featured a single producer in common to the first installment: DJ Premier, the reliable provider of intros. 

This resulted in a brand new sound for Jay, closer to the budding Ruff Ryders aesthetic that would gain further momentum in a few short years. For one, Jay enlisted Swizz Beatz to handle a trifecta of bangers, in return receiving some of Swizzy’s signature unconventionality. Timbaland, at the time gaining notoriety for his work with Missy Elliott and Aalyiah, brought a touch of the future with his own pair of selections; on “N***a What, N***a Who,” Timbo’s uptempo banger led to Jay’s finest double-time bars to date, a title it may still hold today. Lest we forget, under Jaz-O’s tutelage, a young Jay once delivered dexterous tongue-twisting flows on the regular. And what more can be said about the title track, which somehow managed to make Annie The Orphan’s misery into the hardest chorus of the year? 

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That’s not to say remnants of the past went forgotten. Tracks like “A Week Ago” and “Reservoir Dogs” feel comfortable revisiting the Brooklyn underbelly for some crime of the organized variety. Still, Hard Knock Life felt notably polished, a first for Jay. Though it may have led to somewhat of a scattershot listen, looking back, it feels like a beautifully preserved relic of a monumental era in hip-hop history. Perhaps surprisingly, the project went on to become Jay’s best-selling body of work, with 2017 statistics confirming its quintuple-platinum staus.

Though it seldom goes represented as one of Jay’s defining albums, there’s a certain mystique that surrounds it with a notable allure. Perhaps it’s Vol 2’s transitionary nature, foreshadowing a sonic versatility that would follow him well into his career, from the follow-up Vol 3… to Watch The Throne. Or perhaps it’s simply the charisma and lyrical prowess of a young Jay-Z, doing his best to set himself apart from an elite circle of New York contemporaries, from DMX, to Nas, to Ja Rule, to The Lox, to Raekwon, to Ghostface Killah, to Method Man. One day removed from its twenty-first birthday, where do you stand on Hard Knock Life?