Inside the Worst Music Decisions of All Time

chris gaines

Any truly exhaustive list of bad decisions made by musicians would stretch into the thousands, with many duplicate entries for “tried heroin for the first time.”

So Rolling Stone‘s recent list of the top 50 worst choices, created by senior writer Andy Greene, narrowed it down by keeping it mostly light and paying special focus on absurd and career-damning moves. To hear our podcast adaptation of the whole list, listen on Apple Podcasts or Spotify or press play above.

As discussed in the Rolling Stone Music Now episode, which breaks down all 50 entries, the list was created before Kanye West decided to praise Nazis, or else he very likely would’ve taken the Number One slot. Greene also explains some of the more idiosyncratic choices on the list, including a high ranking for ’80s rocker Billy Squier dancing in his notorious video for “Rock Me Tonite.” As with the Spin Doctors choosing the scat-damaged “Cleopatra’s Cat” as the single from their second album (No. 30), Squier’s video was a rare case of an act destroying their entire career in a single moment.


Not all of the mistakes were made by musicians themselves: The list also includes executive errors, including Scooter Braun buying Taylor Swift’s catalog against her wishes, which led to her triumphant Taylor’s Version remakes of her old albums, the devaluation of the original recordings, and widespread opprobrium for Braun. And then there was the time David Geffen sued Neil Young… for not sounding enough like Neil Young.

Download and subscribe to our weekly podcast, Rolling Stone Music Now, hosted by Brian Hiatt, on Apple Podcasts or Spotify (or wherever you get your podcasts), and check out six years’ worth of episodes in the archive, including in-depth, career-spanning interviews with Bruce Springsteen, Mariah Carey, Halsey, Neil Young, Snoop Dogg, Brandi Carlile, Phoebe Bridgers, Rick Ross, Alicia Keys, the National, Ice Cube, Taylor Hawkins, Willow, Keith Richards, Robert Plant, Dua Lipa, Questlove, Killer Mike, Julian Casablancas, Sheryl Crow, Johnny Marr, Scott Weiland, Liam Gallagher, Alice Cooper, Fleetwood Mac, Elvis Costello, John Legend, Donald Fagen, Charlie Puth, Phil Collins, Justin Townes Earle, Stephen Malkmus, Sebastian Bach, Tom Petty, Eddie Van Halen, Kelly Clarkson, Pete Townshend, Bob Seger, the Zombies, Gary Clark Jr., and many others — plus dozens of episodes featuring genre-spanning discussions, debates, and explainers with Rolling Stone’s critics and reporters.


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