Top 10 Musicians Who RUINED Their Reputations with One Song

“Why Can’t I?” (2003)

On Liz Phair’s self-titled 2003 album, the edgy singer-songwriter took a more commercial approach. It was predictably blasted by critics, and the worst offender was the lead single. “Why Can’t I?” faced immense backlash for its poppy subject matter and sound, which was crafted by production team The Matrix, who previously worked with Avril Lavigne. Inspiring comparisons to Michelle Branch and Lavigne herself, “Why Can’t I?” was featured in several rom-coms and totally went against what was expected of Phair. Her following albums, 2005’s “Somebody’s Miracle” and 2010’s “Funstyle” underperformed, and while Phair won some fans with 2021’s “Soberish,” she’s still been exiled from critical darling status.

“White Privilege II” (2016)

People were happy to let Macklemore exist as the corny but well-meaning white rapper with fun songs like “Thrift Shop,” but winning the award for Best Rap Album over Kendrick Lamar was a bridge too far. The controversial win ignited a discussion about white artists in hip-hop spaces and how they’re often rewarded over Black artists. Macklemore responded to the backlash with his track “White Privilege II,” where he acknowledged the advantages he reaps due to his skin color. While he seemed to say the right things, some felt he shouldn’t have said anything and instead continued to listen and learn.

“Flatline” (2016)

Stars have succeeded in spite of their fringe views before. But unlike some of them, B.o.B. doesn’t have the catalog to back up his controversial side. In 2015, the “Airplanes” rapper expressed flat Earth beliefs, Holocaust denial, and support for 9/11, Illuminati, and reptilian conspiracy theories. He even got into a Twitter fight with Neil DeGrasse Tyson, aiming his song “Flatline” at the physicist. The song killed any chance at B.o.B. staging a mainstream comeback, being dragged by critics and receiving a scolding from the president of the Anti-Defamation League. With all said and done, it’s safe to say he could really use a hit right now.

“Intuition” (2003)

With her 2003 song “Intuition” and its parent album “0304,” Jewel attempted a Britney-esque dance style that alienated nearly everyone. Not only did it scare off the acoustic audience she built up in the ‘90s, but the lyrics seemed to be criticizing her new sound while still partaking in it. Jewel also didn’t seem too bothered about disguising her intentions — one of the lyrics is “sell your sin, just cash in.” Considering that “Intuition” was the centerpiece of an ad campaign by Schick razors, that lyric struck a sour note. Although she returned to her previous sound on her next album, 2006’s “Goodbye Alice in Wonderland,” not everyone was on board and she was ultimately dropped from her label, Atlantic Records.

“Literally I Can’t” (2014)

Party rocking isn’t the only thing he has to be sorry for. Redfoo rose to fame as one half of the early-‘10s duo LMFAO. Although they fit in with the popular party music of the time, they struggled to stay relevant as music tastes changed. Redfoo’s guest feature on the 2014 Play-N-Skillz song “Literally I Can’t” came at a moment in his career where every song counted, and it was the wrong one to bet on. Not only was the maximalist EDM production dated on arrival, but his verse tells a woman to shut up and twerk instead of speaking her mind. Insulting half of your audience might not be the best idea when you’re on your fourteenth minute of fame.

“American Life” (2003)

Even the Queen of Pop has an occasional court jester era. While she’d broached controversial subjects before, Madonna became more overtly political than ever on 2003’s “American Life.” On the song, Madonna decried the shallowness of fame, but the messaging was all over the place. It lacked focus and seemed hypocritical given her continued celebrity status, and her attempt at rapping is one of the more awkward moments in her discography. “American Life” became Madonna’s lowest-charting lead single since her early career, peaking at #37 on the Hot 100. She might have recovered for a few more albums starting with 2005’s “Confessions on a Dance Floor,” but “American Life” was the first true crack in the Madonna machine and ended her imperial phase.

“Get Her Back” (2014)

You know his lines are blurred, but that’s probably the last you’ve heard. After Robin Thicke’s 2013 hit “Blurred Lines,” he released the song “Get Her Back” and its album “Paula.” Both are Thicke’s attempt at reconciling with his then-separated wife, actress Paula Patton. In “Get Her Back,” Thicke admits to his regrets in their relationship, and includes alleged texts between the former couple. One exchange goes “I wrote a whole album about you,” with the reply “I don’t care.” Unfortunately for Thicke, neither did anyone else. The song peaked at #82 on the Hot 100, a far cry from “Blurred Lines”’ success. Thicke has since become a panelist on “The Masked Singer,” but the door is closed on his days as a hitmaker.

“Rock Me Tonite” (1984)

Nothing about this song seems like a reputation-killer on its own, but the music video is what pushes it into trainwreck territory. In an era when many rockstars maintained a so-called “macho” image that carried on through their songs, live performances and music videos, Billy Squier released a video that could be described as the exact opposite of that image. With cheesy choreography from future “High School Musical” director Kenny Ortega, the video mostly featured Squier dancing and writhing around a room by himself. While artists like David Bowie and Prince also stepped outside of the 1980s’ rigid gender roles, Squier’s vibe change didn’t go down well with many young rock fans and significantly affected sales of Squier’s subsequent music. Squier says the whole thing is “an MBA course in how a video can go totally wrong.”

“I Disappear” (2000)

Metallica ending its reign would be a true “Mission: Impossible,” but for a while there, they were pretty close. The group’s song “I Disappear” was included in the second installment of the spy movie franchise, and became the nucleus of a Napster drama. Metallica’s drummer Lars Ulrich waged war against the file-sharing site when “I Disappear” leaked onto it, tanking the group’s reputation among music heads. After filing a lawsuit against Napster, which would eventually file for bankruptcy, Ulrich was booed onstage at the 2000 MTV Video Music Awards. To make matters worse, Metallica’s next album, 2003’s “St. Anger” was considered their weakest to date. They’d make a recovery, but for a time, the group seemed hard-wired to self-destruct.

“Girl You Know It’s True” (1988)

This song would make and break its artists. German pop duo Milli Vanilli released “Girl You Know It’s True” in 1988 and followed it up with a trio of #1s. However, a 1989 MTV performance of their debut hit was the beginning of the end. The track skipped, exposing the duo’s lip-syncing, and a year later it would be revealed that they hadn’t sung any of their songs at all. Milli Vanilli’s 1990 Best New Artist Grammy was revoked, and they even faced a class action lawsuit. While they recorded a follow-up later, it never saw the light of day due to member Rob Pilatus’ death. Not only did the controversy kill Milli Vanilli’s careers, but it revealed they were built on lies.


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