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VOICE OVER: Ryan Wild WRITTEN BY: Arianna Wechter
These musicians made some serious mistakes...and it cost them. Welcome to WatchMojo, and today we're counting down our picks for the most pivotal moments in musicians' careers that ultimately led to their downfall. Our countdown of the moments that killed musicians careers includes Ashlee Simpson, DaBaby, R. Kelly, and more!

#10: Lip Syncing on “Saturday Night Live”

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Ashlee Simpson
Artistic integrity is vital for musicians– especially for those just starting out. Ashlee Simpson was still in the early stages of her career when she was billed as a musical guest on “Saturday Night Live”. However, during Simpson’s second performance of the night, things went awry. The vocals for the previous song unexpectedly started playing again, causing her to freeze up and do a little jig. Simpson’s reaction during this mishap and her subsequent explanation became the subject of widespread jokes. What could have been a huge opportunity to expand her audience and further her career ended up derailing it entirely. While she did move on to other ventures, she has since struggled to regain her previous success.

#9: Releasing the “Rock Me Tonite” Music Video

Billy Squier
This has to be the mildest way to lose everything. In the 1980s, Billy Squier gained popularity by releasing rock-inspired songs during the heyday of the New Wave era. However, at his peak, Squier did the unforgivable: he made a slightly cringe-worthy music video. It may seem mild now, but between his pastel outfit and the somewhat campy choreography, Squier lost his rockstar cred and was deserted by many fans of the genre. One of Squier’s managers even tried to prevent the video from being released, but he was shot down by the label executives. The fallout was swift and harsh. Squier went from selling out shows to hardly filling capacity, and eventually retired from the music business completely.

#8: Discounting Misconduct Allegations

CeeLo Green
Responding to criminal allegations is a delicate process– and this singer did it in the worst way possible. When he was accused of sexual assault in 2014, CeeLo Green’s response was baffling. Green not only denied the claim, he took it a step further by tweeting that if the victim was unconscious, then it couldn’t be considered assault. Not only was his statement incorrect and repulsive, it also raised doubts about his innocence. While the assault itself was never tried, Green’s comments were enough to seal his fate in the court of public opinion. Despite his subsequent apologies, he hasn’t been able to attain the level of success he enjoyed just a few years prior.

#7: Making Derogatory Comments Mid-Performance

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DaBaby
Crowd interaction at shows is great, but saying the wrong thing can make everything go south. During his Rolling Loud appearance, DaBaby decided to interact with his supporters in the strangest way possible. Not only did he make disparaging comments about gay men, but he also fed into a negative stigma surrounding diseases like AIDS. Needless to say, it killed both the vibe and his reputation. He was immediately called out by fans, activists, and even other celebrities. He was also dropped from future festivals, and even had his collaboration with Dua Lipa pulled from the radio. His later apology came across as both bizarre and backhanded, which only worked against him. While he still releases music, his image has never been the same.

#6: Becoming a Flat-Earther

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B.o.B
This is probably the worst hill you can choose to die on. The rapper, who gained popularity with hits like “Airplanes”, lost goodwill when he started posting conspiracy theories on his Twitter account. B.o.B’s posts raised questions about the curvature of the planet Earth, which opened him up to widespread ridicule, not only from his fans, but also from esteemed scientists, such as Neil DeGrasse Tyson. Unfortunately, these comments only drove B.o.B further down the rabbit hole, and he emerged a complete flat-earther. He even started a donation page to fund a satellite that would supposedly prove his theory. This was the final nail in his career’s coffin, making this stance his permanent legacy.

#5: Shooting Megan Thee Stallion

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Tory Lanez
This was arguably one of the most intense legal battles in recent entertainment history. After an altercation wherein rapper Megan Thee Stallion was shot, she revealed that the perpetrator was Tory Lanez. Instead of responding with a simple confirmation or denial, Lanez launched a smear campaign against Megan, refuting her claims and calling her a liar. He even addressed the issue repeatedly in his album, stating that Megan tried to frame him. However, once more information surfaced, public opinion turned against Lanez. By the time the case went to trial in 2022, he had already lost a large chunk of his fan base. In 2023, he was eventually convicted on multiple charges and sentenced to a decade in a prison.

#4: Assault Allegations

Marilyn Manson
He’s one of the most contentious figures in modern music for a reason. Manson is no stranger to being called out, but these allegations were the last straw. The rock star was dropped by his label following a series of claims by multiple women, including his former fiancée Evan Rachel Wood. The accusations ranged from Anti-Semitism to sexual assault. While unsavory moments from Manson’s past had made it to the public before, people found it harder to defend him this time around. In addition, his acting roles were pulled due to the controversy. While Manson and his team have vehemently denied the allegations, people aren’t entirely convinced– especially when he claimed his accusers made everything up to cause his downfall.

#3: Ripping Up a Photo of the Pope

Sinéad O’Connor
True courage is standing firm in your beliefs. Sinéad O’Connor proved this during her first and only appearance on “Saturday Night Live”. After her performance, she ripped up a photo of Pope John Paul II, before making a powerful statement. She later explained that she was protesting injustices caused by the institution, such as covering up the exploitation of minors. O’Connor was accused of fomenting violence, and was subsequently blacklisted. She was even threatened by other celebrities. What’s worse is that the Pope seemingly admitted to the cover-ups less than a decade later– but the damage to her career was already done. As time has gone on, more people have realized that she didn’t deserve the backlash, and now commend her bravery.

#2: Being Caught With Inappropriate Images

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Gary Glitter
No matter how long your fame has lasted, there are some things you can never come back from. Gary Glitter, who was once known for his contributions to glam rock, cemented himself with a much more negative legacy. In the late ‘90s, he was arrested and charged with possessing inappropriate material involving minors. After his initial sentence, he traveled around the world, trying and failing to escape his past. Glitter also served prison time in Vietnam for another sex crime and, in 2015, was convicted in the UK of a series of assaults from the late ‘70s and early ‘80s. His name is arguably now more synonymous with his predatory tendencies than his music– and will most likely remain that way.

#1: String of Assault Allegations

R. Kelly
The R&B singer, R. Kelly is no stranger to claims regarding his inappropriate relationships. However, he was still able to continue his career relatively unscathed. It wasn’t until a second round of accusations arose in the 2010s that people started to really distance themselves from him. After allegations of him running a disturbing sex cult came to light, people were horrified. Music platforms stopped promoting his songs, artists condemned their past collaborations, and consumers boycotted his work. While he still maintained his innocence, he was eventually tried and convicted of several different charges. Kelly serves as an example that it doesn’t matter how powerful a person is– they can and will eventually be brought to justice.

What career-ruining moment do you think was the most justified? Let us know in the comments below.

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