Top 20 Worst Decisions in Music History

Top 20 Worst Decisions in Music History

Welcome to WatchMojo, and today we’re counting down our picks for the most disastrous financial and creative decisions in music history.

#20: Bob Dylan Releases “Self Portrait”

The musical genius was riding high as the voice of his generation. Only, Dylan didn’t really like that distinction and wanted to subvert everyone’s expectations for the sole purpose of shaking the obsessive following. So he released Self Portrait, an album with awful production, odd cover songs, and live recordings. Fans eagerly bought the double album expecting another Blonde on Blonde… and they got this instead. Rolling Stone critic Greil Marcus summed up everyone’s thoughts when he opened his famous review with the question “What is this crap?” Only he didn’t say “crap.” To be honest, we don’t know if this was a mistake or just Dylan trolling. Either way, he never really regained his ‘60s relevance.

#19: N.W.A. Signs with Jerry Heller

Signing with Jerry Heller was, in hindsight, like inviting someone to manage your money who seems a little too enthusiastic about managing your money. It’s true that Heller helped take N.W.A. from local legends to arena stars (and controversy magnets), but the contracts he arranged tended to benefit Heller far more than the artists creating the actual music. While N.W.A was challenging authority and creating gangsta rap, Heller was quietly ensuring his own financial security, and often at the band’s own expense. The result was a storm of mistrust, feuding, legal disputes, and lasting resentment that eventually broke apart the group just four years after they formed. In the words of Dre, “The split came when Jerry Heller got involved.”

#18: Ja Rule Creates the Fyre Festival

Ja Rule once helped shape the sound of early 2000s hip hop. Then he helped shape one of the most spectacular failures in music history. Fyre Festival was marketed as an ultra-luxurious getaway with good music, gorgeous villas, gourmet food, expensive yachts, and famous influencers partying in paradise. What attendees actually got was disaster-relief tents, wet mattresses, canceled concerts, and cheese sandwiches. And, like, not even good cheese sandwiches. Instead of launching a lifestyle empire, the event launched news reports, documentaries, and numerous lawsuits that turned Ja Rule into a running joke. He was eventually cleared of all wrongdoing, but his reputation went up in flames.

#17: U2 Forces Their Album Onto Everyone’s iTunes

In what could very nicely be called a bold marketing move, U2 teamed up with Apple to place their new album Songs of Innocence directly into everyone’s iTunes library. The world woke up, checked their phones, and wondered why an album they didn’t buy, or even want, was suddenly taking up space. While Bono thought it would be a gift to humanity, the response was more “please take this off my phone and never do anything like it ever again.” Privacy concerns exploded, memes flooded the internet, and Apple had to release a special tool just to delete the album. And, you know, maybe the backlash wouldn’t have been so bad if this was another Joshua Tree or Achtung Baby. It was not.

#16: Drake Comes After Kendrick

Drake just can’t stop losing. It’s almost sad at this point. His diss track “Duppy Freestyle” caused Pusha T to release “The Story of Adidon,” revealing that Drake had a secret son and arguing that he appropriates black culture. So Drake lost that one. And then he went after Kendrick Lamar. Following a series of increasingly-personal disses, Kendrick released both “Meet the Grahams” and “Not Like Us,” both of which effectively killed Drake in the public perception. Drake sulked away and sued Universal for releasing the song. Kendrick won five Grammys for “Not Like Us” and played it at the Super Bowl. By this point, we could only think of that famous “Simpsons” meme - “Stop, stop, he’s already dead!”

#15: Prince Changes His Name to a Symbol

In the ‘90s, Prince waged war against his record label by changing his name to a symbol unpronounceable by human tongues, although it went by the name “Love Symbol.” As political statements go, pretty bold. As for branding? A bit of a nightmare. Fans didn’t know what to call him, journalists needed special fonts, and the media just ignored the statement by calling him “The Artist Formally Known as Prince.” And his sales plummeted. After adopting the stage name in 1993, he never again had a top five studio album, and only one of eleven reached the top ten. It wasn’t until Musicology in 2004 that Prince again reached the top five - and probably not coincidentally, after changing his name back to Prince.

#14: Elvis Says No to “A Star Is Born”

This is one of the greatest “what ifs” in music history. Barbra Streisand personally approached Elvis Presley to play the male lead in the 1976 remake of “A Star Is Born.” Elvis showed great interest and personally met with Streisand, believing it could revive his career and return him to the big screen after years away. But Elvis’s manager, Colonel Tom Parker, demanded too much money, so negotiations tanked and the gig went to Kris Kristofferson. The film was a huge hit and received four Oscar nominations. Meanwhile, Elvis went back to Vegas, his health worsened further, and he died in 1977 at just 42. A major potential comeback slipped through his fingers, and all because his manager couldn’t resist playing hardball.

#13: Lou Reed Releases “Metal Machine Music”

After leaving The Velvet Underground, Lou Reed seemed poised for a great solo career. “Walk on the Wild Side” was a hit, and 1974’s Sally Can’t Dance was his first top ten album. The next year came Metal Machine Music, and that was about it for Reed. The double album was nothing but screeching guitar feedback. No melody, no structure. Just…noise…pushing the limits of human patience for 64 minutes. Some avant-garde fans called it genius. Everyone else called it unlistenable. Critics assumed it was a prank, record stores wanted it off their shelves, and it was even taken off the market after just three weeks. The album became a benchmark of awful, and Reed never again had a top ten album in America.

#12: Billy Squier Releases The “Rock Me Tonite” Music Video

Billy Squier was riding high with killer rock hits like “The Stroke” - until a disastrous music video sent his career into a nosedive. In “Rock Me Tonite,” Squier prances around a neon bedroom wearing pastel shirts and dancing in ways that hard rock audiences were just not prepared for. Devoted fans fled in droves, concert sales plummeted, and Squier fired his managers. Rock culture and music historians now label it as the defining moment that killed his career - a sentiment that Squier himself agrees with. Ironically, “Rock Me Tonite” is also Squire’s highest-charting single on the Hot 100. Now how many artists can claim that their most successful song is also the one that ruined them forever?

#11: MC Hammer Goes on a Disastrous Spending Spree

MC Hammer proved that “U Can’t Touch This” does not apply to debt collectors. At the height of his fame, MC Hammer was worth about $70 million, but he spent it like money was going out of fashion. Like Hammer pants. He supported friends and family, which is admirable. But he also hired a personal entourage, bought thoroughbred racehorses, collected luxury cars, and invested heavily in a mansion with a price tag worthy of a comic book villain. Before long, the $70 million was blown and he was $13 million in debt. Sales dried up but his debt did not, and Hammer famously filed for bankruptcy in 1996. He became the poster child for music industry overspending, proving that even chart-topping fame has its limits.

#10: Steven Van Zandt Quits The E Street Band

Steven Van Zandt joined Bruce Springsteen’s E Street Band around the time of Born to Run, joining the group for their complimentary 1975 tour. He stayed with the band for a few years before leaving in 1984 to focus on his solo career. Bad move. That same year, Springsteen released the enormously popular Born in the U.S.A., which catapulted both him and the band to superstardom. While Van Zandt co-produced and played on the record, he did not tour for it, replaced by Nils Lofgren. Van Zandt told Rolling Stone in 2020 that leaving the band “was a mistake [he’s] never recovered from” and that “financially, it was apocalyptic.” Still, he later found success as Silvio on “The Sopranos,” so that’s something!

#9: Ashlee Simpson Decides to Lip Sync on “SNL”

Ashlee Simpson was on the rise in the early 2000s, with her debut album Autobiography being a big hit. And then came the legendary night of October 23, 2004. Simpson supposedly had acid reflux that night, so she decided to lip sync her performance on “SNL.” And when the wrong vocal track started playing, the singer froze, did a funny hoedown, and awkwardly jigged her way offstage. Millions watched the moment live, instantly turning her from up-and-comer to a national punchline. It was viral before viral was even a thing. And you know, it wouldn’t be so bad if she didn’t blame her band. But she did, and it was momentous, and it put a permanent stain on Simpson’s professional reputation.

#8: Guns N’ Roses Keep Delaying “Chinese Democracy”

You know what really kills a career? A 15 year gap between projects. Guns N’ Roses were once the coolest band in the world, but their career hit a brick wall in the early ‘90s following The Spaghetti Incident. The band’s follow-up, Chinese Democracy, became Rose’s personal obsession - so much so that it would take over a decade to create. The album was plagued by constant rewrites, rotating band members, relentless in-fighting, and a ballooning production budget that eventually exceeded $13 million. And when the album finally arrived in 2008, it was met with a collective “meh.” It sold well, but few cared for the music, and the band’s reputation remained stuck in the ‘90s.

#7: Garth Brooks Becomes Chris Gaines

In 1999, country megastar Garth Brooks decided to reinvent himself as Chris Gaines - an Australian rock star with emo hair and a soul patch. It was bewildering. Brooks had big plans for Chris, including a fictional biopic, and he appeared as Gaines in a “Saturday Night Live” episode that he was hosting as himself. But the mainstream public had little interest in this Chris Gaines fella, and Brooks fans didn’t want their cowboy God looking like he was cosplaying Professor Snape. Despite a hit song with “Lost in You,” the Gaines character was a huge flop and the movie was canceled before it even began. This curious experiment has gone down as perhaps the most baffling identity crisis in music history.

#6: Milli Vanilli Fake Their Entire Career

This R&B duo had it all - chart-topping hits, Grammys, and the coolest jackets of 1989. Then a disastrous live performance exposed the truth: the duo wasn’t actually singing. In fact, they never were singing. Following the infamous MTV fiasco, the band’s producer, Frank Farian, announced that the vocals actually belonged to different studio singers, not Fab Morvan and Rob Pilatus. The Grammy was revoked, their careers collapsed overnight, and they tried to save face by making them sing for real, but that only made things worse. So instead of being remembered for catchy pop perfection, Milli Vanilli became the universal shorthand for musical fraud.

#5: Simon Cowell Passes on The Spice Girls

Simon Cowell is known for spotting pop gold - but even the best talent scouts miss a few opportunities. Legend has it that The Spice Girls gave an impromptu audition to Cowell in a parking lot, but the music mogul wasn’t impressed and turned them down. Cowell says otherwise, claiming they rejected his offer. Either way, a deal was not made, and these random people off the street soon became the biggest girl group on the planet, selling millions of records and launching a global cultural phenomenon. Cowell later admitted that letting them go was the biggest regret of his career. Instead of riding the Spice hype train all the way to the bank, he watched from the platform as the girls revolutionized pop.

#4: Kanye West Interrupts Taylor Swift at the VMAs

You know, looking back, it was all downhill from here. The 2009 VMAs were going smoothly… until Kanye West stormed the stage, grabbed Taylor Swift’s mic, and declared that Beyoncé should have won instead. The audience booed, the internet exploded, and a massive cultural storm was born. Kanye was already known for being unpredictable and eccentric, but it was this moment that catapulted him into full-on jerk territory, and he hasn’t really let up since. Taylor’s shocked reaction became iconic, Beyoncé looked uncomfortable as all heck, and Kanye’s reputation took a major, permanent hit. If he never stormed this stage and turned himself into a troll, who knows what the future would have held?

#3: Metallica Sues Napster

Metallica helped define the heavy metal rebellion and then stopped their fans from sharing their music. Now how metal is that? When Napster made file-sharing popular in the early 2000s, Metallica became the face of the anti-piracy crackdown. Their arguments about protecting artists’ rights weren’t wrong per se, but the optics were absolutely brutal. Late night shows mocked them endlessly, Lars Ulrich became a meme, and fans accused them of being greedy and selling out to their corporate overlords. The lawsuit helped shut Napster down but damaged Metallica’s cool factor for good. It wasn’t a great PR move for a band once seen as the voice of the people and the downtrodden. Even today, Metallica is still known as The Band That Sued Napster.

#2: The Beatles Hire Allen Klein

There are countless reasons as to why The Beatles broke up, but a big one was Allen Klein. In their final, tension-filled years, The Beatles couldn’t even agree on management. Paul wanted Lee Eastman, a respected business mind (and conveniently, his future father-in-law). The rest chose Allen Klein, a music manager with a reputation bordering on “professional chaos agent.” Klein pushed aggressive financial tactics which strained already-strained relationships to their breaking points and accelerated the group’s breakup. Years later, accusations of mismanagement piled up - along with some lawsuits. Yes, The Beatles already had internal issues, but everything collapsed once Klein took control of Apple.

#1: The Rolling Stones Hire The Hells Angels for Altamont

Numerous things are blamed for “ending” the ‘60s, and the Altamont Free Concert is one of them. Trying to recreate Woodstock on the West Coast, The Rolling Stones hosted the concert - and reportedly allowed their management to hire the Hells Angels as security. And paid them in beer. It was a disaster waiting to happen. The environment soon became dangerous, with countless people being injured, one drowning in a canal, and two being killed in a hit-and-run. And then of course there was the death of Meredith Hunter, stabbed and killed by Hells Angel Alan Passaro. Instead of delivering a harmonious moment of counterculture peace and love, Altamont became a horrifying cautionary tale of violence. Rock and roll may celebrate rebellion, but hiring actual outlaws was a little too on-the-nose.

What do you make of these decisions? Right call or no? Let us know in the comments below!