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The Most Career-Ruining Performances Of All Time

Updated April 23, 2019 11.5k votes 2.1k voters 140.4k views12 items

List RulesWas this career-ending?

Riots, rants, and technical failures - live music comes with plenty of risks. Performances can make or break a musician's career. For every legendary performance that launched a musician's career, there are truly disastrous performances that doomed a musician forever.

We're not talking one-offs - this is about those genuinely bad performances that tanked someone's career. Whether it's because of bad lip-syncing, a wardrobe malfunction, or personal meltdown, some terrible performances have majorly disserviced an artist's career. 

Let's take a look at the most unbelievably bad performances that just about ended it all for the people on stage. 

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  • Milli Vanilli's Lip-Syncing Tr is listed (or ranked) 1 on the list The Most Career-Ruining Performances Of All Time
    Photo: Alan Light / Wikimedia Commons / CC BY 2.0

    Milli Vanilli rocked the charts in the late '80s before a live performance exposed the pop duo, proving they weren't just two good-looking European gentlemen with amazing voices. The truth was revealed when a backing track began to skip during a performance on MTV. The moment spurred speculation about the authenticity of the group's vocals.

    Soon after, their manager revealed they were, in fact, lip-syncing and that session singers had recorded the album. As a result, the duo had their Grammy award taken away; Milli Vanilli was effectively over.

    "It’s like working with smoke and mirrors, nobody knew what was going on for a long time," the group's backup singer, Linda Rocco, later said of the incident.

    Rob Pilatus and Fab Morvan, the faces of the duo, attempted a genuine comeback a few years later but were unsuccessful. 

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  • Ashlee Simpson's Hoedown Debac is listed (or ranked) 2 on the list The Most Career-Ruining Performances Of All Time
    Photo: Glenn Francis / Wikimedia Commons / CC BY 3.0

    Ashlee Simpson, sister of pop star Jessica Simpson, had begun to get her own music career off the ground when she landed a prized spot as a musical guest on Saturday Night Live in 2004. "Pieces Of Me," the first song of the buzzed-about performance, went well enough. But when Simpson took the stage for her second song, the backing track for the first song, "Pieces Of Me," began to play instead.

    Stunned, Simpson performed a brief jig before running off stage. The show went to commercial a minute later. 

    "I’ll hold my head high and say I think it was silly of me to do it, silly of me to blame the band, I was just so f*cking embarrassed," she later said in a statement, blaming the incident on acid reflux and her voice being shot.

    Simpson's subsequent single release did poorly, as did the album that followed. Her musical career never got back on track. 

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  • Lindsay Lohan's Fake Singing is listed (or ranked) 3 on the list The Most Career-Ruining Performances Of All Time
    Photo: Rafael Amado Deras / Wikimedia Commons / CC BY 2.0

    In 2004, actress Lindsay Lohan began her musical career with a scandal: lip-syncing on national television. Lohan was performing two songs from her album when she was caught on camera, apparently forgetting to move her mouth along with the vocals that were playing.

    Reps for both Lohan's record label and Good Morning America denied that she lip-synced. Label rep Kim Jakwerth said in a statement:

    She did not lip-sync. Lindsay sang 100 percent live. Her band played 100 percent live. The background singers were 100 percent live. Yes, on the first song there were background tracks, which were not on the second song.

    The scandal was the beginning of the end for Lohan's musical endeavors, as she never quite recovered enough to keep pursuing a singing career. 

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  • Michelle Shocked's Anti-Gay Ti is listed (or ranked) 4 on the list The Most Career-Ruining Performances Of All Time
    Photo: Sigmund / Wikimedia Commons / CC BY 2.0

    Folk singer Michelle Shocked derailed her career in 2013 after ranting about gay marriage on stage in San Francisco, CA. The singer, whose own sexuality has been fairly ambiguous over the years, said, "When they stop Prop 8 and force priests at gunpoint to marry [homosexual people], it will be the downfall of civilization, and Jesus will come back."

    Backlash immediately ensued, and Shocked went on the Piers Morgan show to set the record straight, but was unable to undo the damage that had been done. She faded into obscurity soon after. 

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