10 Exact Moments Musicians DESTROYED Their Careers

10 Exact Moments Musicians Destroyed Their Careers

Welcome to WatchMojo, and today we’ll be looking at the most pivotal moments that single-handedly sent an artist’s career spiraling right down the drain.


B.o.B Promotes Flat Earth Theories

With chart-topping hits like “Nothin' on You” and “Airplanes,” B.o.B seemed poised to dominate the rap scene in the 2010s. But then he fell down a rabbit hole of conspiracy theories and just never resurfaced. His wildest belief made headlines in 2016 when he boldly declared online that the Earth is flat. This earned him widespread ridicule, not only from fans but also from renowned scientists like Neil deGrasse Tyson, who went as far as dropping a diss track with his nephew to debunk the claims. Unfortunately, after expressing such bizarre conspiracy theories online, it was tough for anyone to take the rapper seriously. His once rising career simply crashed and burned afterwards.

Iggy Azalea Accusations of Cultural Appropriation

Following the massive success of “Fancy,” many pegged rapper Iggy Azalea as a one-hit wonder. However, she defied those expectations, putting out more top-ten hits like “Problem” and “Black Widow.” But just as her star rose, Azalea came under fire over accusations of cultural appropriation. As a white Australian rapper, her use of Black American vernacular and an exaggerated Southern accent raised eyebrows, as many felt she was profiting off Black culture without acknowledging its roots. When Black artists and fans called her out, Azalea responded rather defensively instead of addressing the criticisms in a constructive manner. As this controversy took center stage, her chart success only continued to decline. By 2024, Azalea announced that she was retiring from music.

Natalia Kills & Willy Moon’s Atrocious Judging

Most people understand that every talent show panel needs at least one brutally honest judge—Simon Cowell has practically built an entire career out of that. But the critiques from said judge still need to be reasonable, and that’s where Natalia Kills and Willy Moon fell short. The married singers joined the judging panel of “The X Factor New Zealand,” only to destroy their careers in the very first live show. Kills and Moon humiliated contestant Joe Irvine, accusing him of copying Moon’s style and lacking originality, even though Irvine was simply wearing a suit with slicked-back hair. Their harsh comments were met with immediate backlash and led to their dismissal from the show, ending any chance they had of music stardom.


Michelle Shocked’s Shocking Rant

Once regarded as a gay icon, this singer’s remarks at a 2013 concert took many fans by surprise. While performing in San Francisco, of all places, Michelle Shocked lived up to her name and left everyone shell-shocked with a bizarre homophobic rant against same-sex marriage. This led many fans to walkout in protest, prompting the club to cut off her microphone and end the show abruptly. She faced widespread condemnation from the LGBTQ+ community, and the remaining dates of her tour were canceled as a result. Despite her attempts to clarify her statements and downplay the incident, the damage was already done. Following this debacle, Shocked largely faded from the spotlight and has released no new music since.


Milli Vanilli’s Lip-Sync Fail

When you market yourself as a music artist, fans naturally expect you to sing your own songs. So many were rightfully disappointed when it was revealed that R&B duo Milli Vanilli had hired other vocalists to sing on their records. The scandal first gained traction in July 1989 during a live performance on MTV. While singing their hit song “Girl You Know It's True,” the pre-recorded track began to skip, causing the chorus to repeat endlessly. Unable to lip-sync over the malfunctioning track, Rob Pilatus panicked and fled the stage. This was the beginning of their end. Once the scandal fully broke, Milli Vanilli lost everything, including their Grammy Award, their record label deal and whatever was left of their music career.


Ashlee Simpson’s “SNL” Gaffe

Performing as the musical guest on “Saturday Night Live” can either propel you to stardom, like it did for Adele, or completely ruin your prospects, as Ashlee Simpson can testify. In October 2004, Simpson was still early in her career when she landed the gig, a prime opportunity to establish herself with a broad audience. After her first performance went well, things quickly unraveled when she climbed the stage a second time. The pre-recorded track from the previous song began playing again, revealing that she had lip-synced the performance. Simpson froze, then broke into a strange hoedown before awkwardly walking off the stage and leaving her band to continue playing. Just like that, her music career ended before it could even begin.


Billy Squier’s Cheesy Music Video

For most of the early 1980s, Billy Squier did everything right. He put out a string of platinum-selling albums, top 10 hits and beloved music videos. But then, one misstep changed everything. In 1984, Squier released the music video for his hit single “Rock Me Tonite,” which didn’t quite rock his fans as much as it left them cringing. His offenses? Wearing a pink tank top in one scene and prancing around in a pastel-colored room in another. Today, it may not seem like a big deal, but back then, it cost Squier his rockstar credibility. While the song remained pretty successful, the accompanying clip put off many fans, who stopped buying his music and attending his shows. Ultimately, Squier retired from the business altogether.



CeeLo Green’s Controversial Tweet

After going on a date with a woman in 2012, singer CeeLo Green faced accusations of sexual battery. This ultimately led to him pleading no contest to furnishing a controlled substance. But Green disagreed with this outcome and he took to Twitter to express his frustration. In his tweet, he attempted to redefine sexual assault by suggesting it is invalid if the victim is unconscious. Needless to say, this was incorrect and deeply insensitive, and many online users did well to let him know that. The backlash from Green’s comments led to his reality show “The Good Life” being canceled just days later. If there was anything his tweets succeeded in redefining, it was his public image… for the worse.


DaBaby’s Derogatory Tirade

People attend music festivals to unwind and have fun. However, those who were present at the 2021 Rolling Loud Festival in Miami saw that mood shift quickly after DaBaby took the stage. For some reason, the rapper launched into a bizarre tirade mid-performance, making disparaging remarks about gay men, and spreading disinformation about people living with HIV. This was sure to have some effect on his career, but had he issued a sincere apology afterwards, the damage might have been mitigated. Instead, DaBaby doubled down on his remarks and even lashed out at his critics. When he finally apologized days later, he was already being dropped from other festivals, and his response was seen as too little too late.


Tory Lanez Shooting Incident


After a July 2020 party in Hollywood Hills, rapper Megan Thee Stallion revealed that she had been shot in the foot. At first, the shooter’s identity was unclear, but it later emerged that fellow rapper Tory Lanez was responsible. Initially, Lanez denied the allegations, even releasing an album that alluded to his innocence and launching a smear campaign against Megan. However, as more details surfaced, public support shifted decisively towards her. In October 2020, Lanez was indicted and arraigned on charges related to the incident. Ultimately, after losing in the court of public opinion, he ended up losing in an actual court and was convicted of three felony charges. This earned him a 10-year prison sentence, effectively gutting his once-promising trajectory.


Do you think any of these musicians will be making a comeback anytime soon? Let us know in the comments below.