Feat. Don’t Fail Me Now

Twenty-five years ago, in late July 1990, the Billboard Hot 100 welcomed a No. 1 single that, while very mediocre, would turn out to be quietly historic: the first of a new breed of chart-topper.

The song was “She Ain’t Worth It,” a one-off pairing between Hawaiian pop crooner Glenn Medeiros and—dropping in more than halfway through with a rap bridge—New Jack Swing megastar Bobby Brown. Forgettable as it was, “Ain’t” holds two...

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