11 Songs That Damaged Singers' Careers
11 Songs That Damaged Singers' Careers
Kristen HarrisSat, October 17, 2026 at 8:31 PM UTC
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One iconic rock star said, "The tour before, I was selling out arenas faster than Sinatra, and as soon as that video came out, I was playing to half houses."It's no fun when your favorite artist puts out a song that blatantly sucks. But what happens when that song is so bad, it effectively derails their whole career?Here are 11 songs that had absolutely disastrous effects on artists' careers:1. In the late '00s/early '10s, Katy Perry hit the scene with one banger after another, such as "Teenage Dream" and "Firework." However, her 2017 album Witness was a commercial and critical flop (and that strange 96-hour promotional livestream certainly didn't help). After releasing another flop album in 2020, she poised herself for another attempt at a comeback. Her 2024 single "Woman's World" finally had everybody talking about her again — but this time, it was for all the wrong reasons.
Capitol Records / Viayoutube.comThe song is an underbaked attempt at feminist empowerment, featuring lyrics like, "Sexy, confident / So intelligent / She is heaven-sent / So soft, so strong" and "It's a woman's world, and you're lucky to be livin' in it." The music video did it no favors, featuring Katy as a sexy Rosie the Riveter surrounded by a crew of construction worker ladies. Halfway through the video, she's crushed by a giant anvil and reawakens as some kind of bionic woman. She "refuels" by sticking a gas pump nozzle into her butt cheek. At the end, she joins another woman in a TikTok dance, then steals her ring light before flying off in a helicopter.
Capitol Records / Viayoutube.comThe comments on the music video speak for themselves:
YouTube / Viayoutube.com
Responding to the criticism in an Instagram video, Katy said, "We're kind of just having fun being a bit sarcastic with it. It's very slapstick and very on the nose, and with this set, it's like, 'Ooh, we're like, we're not about the male gaze, but we really are about the male gaze.' And we're really overplaying it and on the nose because we're about to get smashed, which is like a reset, a reset for me, and a reset for my idea of feminine divine. And it's a whole different world we go to after this."
However, the crux of the backlash came from the fact that "Woman's World" was produced by Dr. Luke (Lukasz Gottwald), whom Keshaaccused of sexual abuse, which he denied.
Joe Scarnici / FilmMagic / Via Getty
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In 2014, Kesha sued Dr. Luke for alleged sexual abuse, and the two spent years in a complicated legal battle. Because she was locked in a contract, Kesha was unable to record new music until 2016, when Sony finally permitted her to record without the producer. In 2023, Kesha and Dr. Luke settled their legal battle a month before it was set to go to trial.
Lorne Thomson / Redferns / Via Getty
In her statement, Kesha said, "Only God knows what happened that night. As I have always said, I cannot recount everything that happened. I am looking forward to closing the door on this chapter of my life and beginning a new one. I wish nothing but peace to all parties involved."
In his statement, Dr. Luke said, “While I appreciate Kesha again acknowledging that she cannot recount what happened that night in 2005, I am absolutely certain that nothing happened. I never drugged or assaulted her and would never do that to anyone. For the sake of my family, I have vigorously fought to clear my name for nearly 10 years. It is time for me to put this difficult matter behind me and move on with my life. I wish Kesha well."
The announcement came several months after the release of Gag Order, Kesha's final album with Dr. Luke's Kemosabe Records. She officially parted ways with the label that December.
On Call Her Daddy, Katy said, "I understand that [collaborating with Dr. Luke] started a lot of conversations. He was one of many collaborators that I collaborated with. But the reality is, it comes from me. The truth is, I wrote these songs from my experience of my whole life going through this metamorphosis. And he was one of the people to help facilitate all that. One of the writers, one of the producers. I am speaking from my own experience. When I speak about 'Woman's World,' I speak about feeling so empowered now as a mother, as a woman, giving birth, creating life, creating another set of organs, a brain, a heart — I created a whole ass heart! ... I created all of this with several different collaborators — people that I've collaborated with from the past, from the 'Teenage Dream' era, from all of that."
Chloe Kern / WireImage / Via Getty
Her next album, 143, charted at #6 on the Billboard Top Album Sales, but it was pretty widely panned by reviewers. Her most recent singles have also underperformed.
2. In 2009, Keri Hilson reached #4 on the Billboard Top 200 with her debut solo album In a Perfect World... and #15 on the Hot 100 with her single "Turnin Me On." However, trouble came knocking with the release of her "Turnin Me On" remix in March 2009. This verse was widely interpreted as shade toward Beyoncé (note the not-so-subtle "Irreplaceable" reference): "Your vision cloudy if you think that you're the best / You can dance, she can sing, but she need to move it to the left, left / She need to go have some babies. She needs to sit down, she fake / I ain't turning it off, I'm stay turning it on. / Go 'head and tell these folks how long I've been writing your songs."
Mosley / Zone 4 / Viayoutube.comBeyoncé's fanbase is known for its loyalty, so, unsurprisingly, they widely criticized Keri. Her sophomore album, No Boys Allowed, produced the hit "Pretty Girl Rock," but afterward, she ended up taking a hiatus until 2025. Behind the scenes, she was going through mental health struggles. She told People, "I was also depressed at the new height of my career with the success of 'Pretty Girl Rock.' I was just not okay. I was not well; I needed a break. I hadn't taken a break since I was 14 years old in my first girl group. When we disbanded, I went headfirst into songwriting at 17, got my first big check by 18. I joined another group and was also writing while in college. So I never had a break from 14 to, say, mid-20s."
Kevin Winter/DCNYRE2010 / Via Getty
"It was already a decade of just pure dedication, and I needed a break. Fame was a beast for me, and I fell into a really dark place. I needed to step away for a moment. I thought it'd be just a one-year moment, not a 14-year moment, but it turns out it was necessary. I really can't regret it. I, as a human, needed that time," she said.
However, a 14-year hiatus still wasn't long enough for the burn of the Beyoncé controversy to fade. In 2025, Keri finally set the record straight, telling The Breakfast Club, "It's a regret, but not in the way people would think, because that's a song I actually didn't write. Those are not my words." She claimed that her producer at the time really wanted to get the remix ready for the album release, so he had another writer pen the shady verse.
Leon Bennett / Getty Images for ESSENCE
She continued, "I come into the studio, and he plays me this verse. Automatically, I was like, 'I'm not saying that.' That was my position.' ... I tried to fight him on it, and I began writing my own, but he… It was quite forceful. In an executive-artist way. Involving others and kind of threatening my career, in a real sense. My album wasn't out yet, so it was like, 'You're not coming out if you don't do this.' The mistake that I made was not continuing to fight, but I was in tears. I was crying. I was adamant that I did not wanna do that."
Keri alleged that she was permitted to write her own verse on the grounds that she recorded the original one first, and then they'd decide which cut to use. However, just a few days later, the original recording conveniently leaked. She said, "That was that. And I protected him. I protected the girl that wrote it, who went on to become famous. I protected everyone in the story, so I have to eat that, and I'm still eating it to this day. It's like I've worn the scarlet letter."
Prince Williams / WireImage / Via Getty
In a statement, Ester Dean, the self-identified cowriter, said, "I submitted a lot of verses for that remix. One got picked, and it was co-written with Keri. Looking back, it was childish and didn't age well. I see how it hurt people, especially women, and I take full accountability. I'm sorry for my part in it. Growth is real, and so is this apology."
Interscope Records and Timbaland's reps didn't respond to Entertainment Weekly's requests for comment at the time.
3. In 2010, B.o.B broke out with two hit singles — "Nothin' on You" and "Airplanes." Over the next few years, he racked up Grammy nominations. However, in 2016, he decided to tell Twitter that he's a flat-earther. He tweeted, "There's no way u can see all the evidence and not know... grow up." Famed astrophysicist Neil deGrasse Tysonmade several tweets correcting him with facts proving the Earth is round, adding, "Flat Earth is a problem only when people in charge think that way. No law stops you from regressively basking in it."
Prince Williams / WireImage / Via GettyRather than reason, B.o.B responded with a diss track. "Flatline" includes faux-enlightened lyrics such as "Aye, Neil Tyson need to loosen up his vest / They probably write that man one hell of a check" and "indoctrinated in a cult called science." He also name-dropped Holocaust denier David Irving.
Earl Gibson III / Getty Images
The David Irving reference and other lyrics in the song have been criticized as antisemitic. In 2022, Jewish students at UCF protested his on-campus concert. He told TMZ, "There were threats to cancel the show, but everything got worked out. I feel like a lot of things got blown out of proportion from that whole time period."
Neil then went on The Nightly Show With Larry Wilmore to address B.o.B's conspiracies. He said, "Listen, B.o.B, once and for all, the Earth looks flat because, one, you're not far enough away at your size. Two, your size isn't large enough relative to Earth to notice any curvature at all. It's a fundamental fact of calculus and non-Euclidean geometry [that] small sections of large curved surfaces will always look flat to little creatures that crawl upon it."
Dominik Bindl / Getty Images
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However, B.o.B doubled down on his flat-earther BS to a ridiculous degree. In 2017, he created a $1 million GoFundMe fundraiser titled "Show BoB the curve," with the goal of helping him "purchase and launch multiple satellites into space" to "find the curve." His career success flatlined, as his following albums failed to chart.
Dimitrios Kambouris / Getty Images4. Sometimes, a wannabe artist's debut single is so bad that it kills any chance they had at a music career. In 2005, Kevin Federline, aka Britney Spears's then-husband, released his debut rap track, "PopoZão." In the lyrics, he claims, "In Portuguese, it means, 'Bring your ass.'" (The song is, to put it lightly, the worst thing I've ever heard in my life. Why did I write this article? Why did I do this to myself?) "PopoZão" was widely mocked, with Today declaring, "What's Portuguese for 'no-talent hack'?"
F. Micelotta / Getty ImagesWhen he released his debut album, Playing With Fire, the following year, "PopoZão" did not make the final tracklist. To no one's surprise, the album was widely panned, scoring an impressively dismal 15/100 on Metacritic. Kevin didn't attempt to release an album again.
James Devaney / WireImage / Via Getty5. Rock star Billy Squier took the '80s by storm, dropping two multi-platinum albums in only two years. His fourth album, Signs of Life, was poised to be a smash off the success of the single "Rock Me Tonite," which peaked at #15 on the Hot 100. But, ironically, "Rock Me Tonite" would end up tanking his career. The issue wasn't the song — it was the music video!
Gary Gershoff / Getty ImagesIn the Kenny Ortega-choreographed video, Billy dances around a pastel bedroom in a pink tank top. From a 2026 perspective, this kind of sounds like a rejected Harry Styles concept. However, in 1984, it was so out of left field for a rock star that it killed his career momentum! The video was swiftly pulled from MTV. Billy fired his managers and blamed them for changing his original idea, which they denied. He reportedly said, "The video had a deleterious effect on my career. The tour before, I was selling out arenas faster than Sinatra, and as soon as that video came out, I was playing to half houses."
Capitol / Viayoutube.com6. From the beginning, Rick Ross was poised for greatness. Jay-Z signed him to Island Def Jam after a bidding war on the back of his underground success. His first three albums all charted at #1 on the Billboard Hot 200. But then, in 2013, he was featured on Rocko's "U.O.E.N.O." On the second verse, Rick rapped, "Put molly all in her champagne / She ain't even know it / I took her home and I enjoyed that / She ain't even know it." (For context, "molly" refers to crystallized MDMA.)
Julia Beverly / Getty ImagesIt took several weeks for listeners to catch on, but eventually, he faced backlash for seemingly referring to date rape in his lyrics. A Change.org petition was launched, calling for him to "publicly apologize for glorifying drugging/raping a woman." He was also criticized by activists and boycotted by at least one radio station.
Chris McKay / WireImage / Via Getty
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In response, he told Q93.3 FM, "There's certain things you can't tweet. I want to make sure this is clear, that woman is the most precious gift known to man, you understand? There was a misunderstanding with a lyric, a misinterpretation. The term rape wasn't used. I would never use the term rape in my records. As far as my camp, hip-hop don't condone that, the streets don't condone that, nobody condones that. So I just wanted to reach out to all the queens that's on my timeline, all the sexy ladies, the beautiful ladies that had been reaching out to me with the misunderstanding. We don't condone rape, and I'm not with that." Big surprise, this apology didn't go down well.
Alexander Tamargo / Getty Images for Reebok
At the time, a Def Jam rep told Billboard that Rick and his label had no further comment.
Reebok dropped Rick, who'd been the face of its Classics line, in the wake of the backlash. In a statement, the brand said, "While we do not believe that Rick Ross condones sexual assault, we are very disappointed he has yet to display an understanding of the seriousness of this issue or an appropriate level of remorse. At this time, it is in everyone's best interest for Reebok to end its partnership with Mr. Ross." Additionally, Rocko also removed his verse and replaced him with Wiz Khalifa, telling Hot 97, "Because of the type of attraction the record has as far as, like, radio and all over the country…it puts me in a position to where I have to change it."
Prince Williams / WireImage / Via Getty
The scandal didn't appear to have a long-term effect on Rick's career at first, as his next album, 2014's Mastermind, peaked at #1, but it turned out to be his last chart topper. In more recent years, his ability to chart highly has slipped. He's also had several more controversies, such as when he pleaded guilty to misdemeanor kidnapping and assault charges in 2017 and when he performed at Trump's Crypto Ball in 2025.
He peaked at #39 with 2026's Set in Stone.
7. In 2013, Robin Thicke had his mainstream breakthrough with the controversial hit "Blurred Lines," which was criticized for being sexist and promoting rape culture. The following year, he separated from his wife and high school sweetheart, Paula Patton. However, rather than accept that the relationship was over, he very publicly shared his desire to "get her back" while onstage at a concert. What was his grand plan? He dedicated his seventh album, 2014's Paula, to her.
Lars Niki / Corbis via Getty ImagesHe promoted the album with the single "Get Her Back," and the music video featured some pretty disturbing imagery, such as skulls and Robin with blood on his face. Compared to the Blurred Lines album, Paula was a flop, selling 24,000 copies in the US during its first week. What's worse, the album was criticized as "creepy." The Atlantic even called it "one of the creepiest albums ever made!" Robin never did get Paula back (good for her!), nor did he ever recapture the success of "Blurred Lines."
Star Trak / Interscope / Viayoutube.com8. Redfoo and his nephew, Sky Blu, rose to fame as the hip-hop duo LMFAO, which scored two #1 hits in 2011 — "Party Rock Anthem" and "Sexy and I Know It." But after LMFAO went on hiatus in 2012, Redfoo went solo, and in 2014, he was featured on "Literally I Can't" by Play-N-Skillz, which Complex called "literally everything wrong with EDM." The song basically mocks women for telling pushy men no. (Also, the song just sucks.) His verse included the lyrics, "But you annoying me...'cause you're talkin" and "I'm tryna see what you got / Not tryna hear what you think."
Dave Hogan/MTV 2014 / Getty Images for MTVThe song was accompanied by an equally appalling music video where sorority girls at a frat party were told to "shut the fuck up" after repeatedly rejecting the boys' advances. Both the song and the music video were widely criticized as misogynistic and for promoting rape culture. In response, Redfoo tweeted, "Another example of critics victimizing an artist by purposely misinterpreting his/her work to support a pre-existing agenda."
Party Rock / Viayoutube.comRedfoo still had another foot to put in his mouth, which he promptly did by blaming female bloggers for creating the backlash. At the time, one woman had launched a petition to have him removed as a judge on The X Factor Australia. On Australian radio, he said, "The women have gone crazy on me. ... I happened to be the biggest target, and getting the darts thrown at me and all this stuff. I was like, whoa, we were just trying to make a fun song. A party song. Having fun."
Robert Cianflone / Getty Images
He continued, "This isn't the first time that someone has had an issue with an artist doing something, or a song — even my song and lyrics. And what I realize at the end of the day is that I love everybody, and I have fans that are from 3 to 93."
Additionally, the label added a disclaimer to the since-removed music video: "The following is a satirical video based on Sororities/Fraternities and the cliche 'Literally I Can't.' This content is in no way to be interpreted as misogynistic or negative towards any groups of people. It is an art piece and it shall be taken as such."
Later, Redfoo issued an apology on Facebook, writing, "I get excited to create things that will unite all of us through laughter, dance & celebration. If during that process I offend anyone, I apologize from the bottom of my heart. In the future I will be more mindful of the way I present my art." As a solo artist, he's never managed to recapture the success of LMFAO. His latest release was 2023's "Long Live Party Rock." More recently, he's switched paths to professional tennis.
Paul Archuleta / Getty Images9. Hits like "Sk8er Boi" and "Girlfriend" made Avril Lavigne a pop-punk icon in the '00s. But then, in 2014, she released the Japan-inspired single "Hello Kitty," which includes lyrics such as, "Like a fat kid on a pack of Smarties / Someone chuck a cupcake at me," "Hello kitty, you're so pretty," and "Kawaii!" She told Digital Spy, "Obviously it's flirtatious and somewhat sexual, but it's genuinely about my love for Hello Kitty as well!" However, the real controversy came from the music video, in which Avril dances around Tokyo with four stone-faced Asian backup dancers in identical outfits.
Epic / Viayoutube.comThe song came from her fifth album, Avril Lavigne, which was already her lowest-selling album in the US at the time (though it went platinum in Japan). The millennial cringe music video did her no favors, with critics branding it "abhorrent" and "offensive." Billboard even called it an "embarrassment in any language." Addressing the criticism, Avril tweeted, "RACIST??? LOLOLOL!!! I love Japanese culture and I spend half of my time in Japan. I flew to Tokyo to shoot this video…"
Epic / Viayoutube.com
She continued, "…specifically for my Japanese fans, WITH my Japanese label, Japanese choreographers AND a Japanese director IN Japan."
While the video didn't go over well with Western audiences, fans in Japan felt differently. Nobuyuki Hayashi, a tech and social media expert in Tokyo, told Billboard, "Searches in the Japanese Twittersphere and blogsphere show that most of the reactions were favorable. The people who are blaming the artist for racism are non-Japanese … but most Japanese people are not taking it that seriously."
Epic / Viayoutube.com
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Overall, "Hello Kitty" charted at #75 on the Billboard Hot 100. Avril's next single, "Give You What You Like," failed to chart. She didn't release another solo single until 2018's "Head Above Water," which peaked at #64. It was her last single to hit the Billboard Hot 100.
Noam Galai / Getty Images10. Sometimes, a song doesn't directly damage an artist's reputation, but the drama surrounding it can have catastrophic consequences. That's what happened with Van Halen's "Humans Being." Lead singer Sammy Hagar, who had replaced David Lee Roth in 1985, was already at odds with the rest of the band after making 1995's Balance, and he wanted some time apart. But Van Halen soon had to reconvene to record music for the Twister soundtrack. While working on "Humans Being," tensions worsened. Eddie Van Halen reportedly hated Sammy's original lyrics, particularly all the weather metaphors.
Jim Steinfeldt / Getty ImagesThere was another source of tension in the band — their greatest hits album, which Sammy didn't really want to do. He told Loudwire, "The new manager that came in wanted us to do a greatest-hits record with both Dave's era and my era with two new songs from me and, not to my knowledge at the time, two more songs from Dave. We ended up using one of them for Twister, and that was the end of the band. I wanted to do a whole record. I didn't want to do a greatest hit record. I didn't think Van Halen was there yet."
Jim Smeal / Ron Galella Collection via Getty ImagesSo, Sammy left Van Halen, and he was replaced by Gary Cherone. Their next album, Van Halen III, charted at #4, breaking their #1 album streak. It was also critically panned, and for the tour, ticket sales were mediocre. In 1999, Alex Van Halen asked Gary to leave the band.
Tim Mosenfelder / Getty ImagesSammy and Eddie later reunited for the 2004 reunion tour, but they "bumped heads" when Sammy called Eddie out for performing poorly. Sammy told Howard Stern, "Ed was sick. I didn't realize…no one realized how sick he really was, obviously, until it was over. It's really a shame. I mean, if there's anything that I regret, it's ever going through any hardships with Eddie because knowing he was sick like that, I would have been so much more compassionate." Thankfully, they made amends after George Lopez called Sammy, urging him to call Eddie because he was "really sick." So, he did. Sammy said, "That’s when we made friends again — it was beautiful."
SiriusXM / Viayoutube.com11. And finally, not every failed song flops because it's bad — sometimes, circumstances are wildly out of an artist's control. In the summer of 2001, Willa Ford released her debut single "I Wanna Be Bad." The song was moderately successful, charting at #22 on the Billboard Hot 100. She released her first album, Willa Was Here, and followed up with her second single, "Did Ya' Understand That," a few months later. (The song is a fairly basic, if forgettable, Y2K pop song that kinda gives "No Scrubs" by TLC vibes.) She told Billboard, "A lot of people don't realize this, but my second single was released on September 11, 2001. Everything that happened that day froze; the world stood still, as it should have. My second single didn't do well because anything that launched that day kind of got canned."
Lava / Atlantic / Viayoutube.comOn top of the tragedy, Willa's record label was also in turmoil between different takeovers, so, ultimately, she decided to walk away. She said, "I really took a step back because I felt like I wasn't doing what I was supposed to be doing at the time. I know that sounds crazy, but it was the perfect storm, and I walked away. It's really hard when you walk away to go back to it." She transitioned to acting before finding a new calling — interior design.
Theo Wargo / WireImage / Via GettyMoreover, Willa does not believe that 9/11 "ruined" her music career. She told Paper magazine, "I don't feel like it derailed me. I do feel like there was just so much of a shift in society and in the world, in general. Who was it not weird for? Who was it not strange for? I had been living in New York at the time when it all happened. The whole thing was just really devastating, and even after there were so many amazing shows put together by so many artists... we were all coming together... doing what we could for the families who were suffering. It affected everybody differently. I'm going to stay away from: Did it affect my career? No, the path that happened for me is exactly how it was supposed to happen."
Bravo / Charles Sykes/Bravo via Getty Images
"I'm a firm believer that everything happens for a reason, and everything I learned has been so helpful now for doing interior design on TV. It's not something that I necessarily anticipated, but it definitely gave me such a leg up to already have all that background. The other day, I was doing teleprompter work," she said.
Has a terrible song ever killed your love for an artist? Why? Share your thoughts in the comments or in the anonymous comments box below!
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