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Kelly Osbourne: “Papa Don’t Preach”
Epic Records, 2002
Pitchfork Rating: 3.7

In a move that can only be described as “aggressively Y2K,” Kelly Osbourne—daughter of Ozzy, wearer of neon hair, and survivor of MTV’s The Osbournes—emerged from the reality-TV fog of war to drop her cover of Madonna’s “Papa Don’t Preach.” A bold choice, given that Madonna’s version is iconic, controversial, and, crucially, good. Kelly’s version? It exists.

Let’s be clear: this is not so much a cover as it is a hostage situation. The song has been taken, tied to a chair in a Hot Topic changing room, and forced to watch early-2000s nu-metal music videos on loop. Guitars are over-distorted. The vocals sound like they were recorded on a Motorola Razr during a family argument. The production is less “punk rebellion” and more “GarageBand preset titled ‘Mall Goth.’”

Osbourne’s voice, while not the worst thing to ever emerge from a celebrity lineage (looking at you, The Return of Bruno), delivers the lyrics with all the emotional depth of a mildly annoyed barista. When she pleads, “I’m keeping my baby,” it sounds less like defiance and more like someone refusing to return a damaged Forever 21 item without a receipt.

That said, there’s a perverse charm to it. Like a can of expired Monster Energy found under a car seat, it’s a little gross, vaguely threatening, and very much a product of its time. There’s even something punk in the audacity of it all—less “fight the system” and more “I dared my label to let me do this and they blinked.”

Ultimately, Kelly Osbourne’s “Papa Don’t Preach” is the kind of cover that reminds you of how great the original was, mainly because halfway through, you’ll probably stop and listen to Madonna’s instead. And maybe that’s the point. Or maybe it’s just a vibe. A crunchy, chaotic, eyeliner-smeared vibe.

Best Track: The 1986 original
RIYL: Watching VH1 at 2 am, burning your ex’s hoodie, riding in the backseat of a PT Cruiser.

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446 episodes