Lauryn Hill’s The Miseducation of Lauryn Hill dropped in 1998 and instantly felt like a cultural event—blending hip-hop, soul, reggae, and R&B into something that was both deeply personal and universally resonant. The album covers everything from love and heartbreak to spirituality and identity, all with Hill’s unmatched mix of sharp lyricism and raw emotion. It’s the kind of record that defined an era but still feels timeless every time you put it on. The big question is: does its legacy and influence justify Rolling Stone ranking it as the #10 greatest album of all time, or is that placement more about the mythos around Lauryn’s one-and-done masterpiece?

Album Recommendations:

• Black on Both Sides - Mos Def
• Goodies - Ciara

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Cover art by Katherine Evans

Theme music: "Tagalong" by Blaise Gratton