The 25 worst cover songs of all time, ranked

Even great musicians with the best intentions can serve up a bad cover of a cherished song. In some cases they might try too hard to be faithful to the original, leading to an interpretation that’s too stiff or slick. Or they can alter a song until it contains just the vaguest air of what made the first version special. In some cases they can wildly misconstrue the classic track, turning their take into a memorable monstrosity.

Whatever the reason for the failings by these artists, there’s no disputing that the original songs remain beloved, which is why brutally bad updates can be so difficult to swallow. This list of the 25 worst cover songs, like our look at the 25 best cover songs of all time, doesn’t pretend to be comprehensive. Still, as we surveyed the last five decades of pop and rock music, we’ve done our best to corral the truly awful covers and order them in a way that metes out some semblance of order, if not justice.

3. Madonna, “American Pie” (2000)

Madonna was in an artistic renaissance during the Y2K era, so the existence of her electro-pop cover of Don McLean’s “American Pie” is all the more baffling. The problem isn’t that Madonna’s synthesized revision—and systemic edit—of McLean’s boomer allegory is sacrilegious. Quite the opposite, actually. Madonna may shift around the lyrics and dress the melody in electronic pulses, yet she retains a sense of pervasive nostalgia—maybe not for the day the music died but rather the time when McLean’s eight-minute ramble could still be heard on a regular basis spilling out of AM radios from coast to coast.