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From career-killing blunders to financial disasters, these moves made music history for all the wrong reasons! Join us as we count down the most catastrophic decisions made by musicians and industry executives. From lip-sync scandals and bizarre alter egos to lawsuits that backfired and management disasters, these choices changed careers forever.
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00:00Lost in your wonderful ways
00:05Welcome to WatchMojo!
00:07And today, we're counting down our picks for the most disastrous financial and creative decisions in music history.
00:14We have a comment from one of our producers, Ricky Camilleri, saying,
00:17Does Lars regret the way in which he handled Napster back in the day?
00:22Number 20. Bob Dylan Releases Self-Portrait.
00:30The musical genius was riding high as the voice of his generation.
00:36Only, Dylan didn't really like that distinction and wanted to subvert everyone's expectations for the sole purpose of shaking the obsessive following.
00:45So, he released Self-Portrait, an album with awful production, odd cover songs, and live recordings.
00:52Fans eagerly bought the double album expecting another blonde-on-blonde, and they got this instead.
00:58Rolling Stone critic Grail Marcus summed up everyone's thoughts when he opened up his famous review with the question,
01:05What is this crap?
01:06Only, he didn't say crap.
01:08To be honest, we don't know if this was a mistake or just Dylan trolling.
01:13Either way, he never really regained his 60s relevance.
01:17Number 19. NWA Signs With Jerry Heller.
01:29You are now about to witness the strength of street knowledge.
01:33Signing with Jerry Heller was, in hindsight, like inviting someone to manage your money who seems a little too enthusiastic about managing your money.
01:41It's true that Heller helped take NWA 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.
01:55While NWA was challenging authority and creating gangster rap, Heller was quietly ensuring his own financial security, and often at the band's own expense.
02:05The result was a storm of mistrust, feuding, legal disputes, and lasting resentment that eventually broke apart the group just four years after they formed.
02:15In the words of Dre, the split came when Jerry Heller got involved.
02:21Jerry took advantage of you.
02:23I know it's a lot, but you had to know the truth sometime.
02:28Now you do.
02:30You know, Dre and Cube tried to warn me about this.
02:35Number 18. Ja Rule Creates The Fyre Festival.
02:39We got major news. Ja Rule just called us.
02:42Basically said he wants us to pitch him for his new app, Fyre.
02:46Ja Rule once helped shape the sound of early 2000s hip-hop.
02:50Then, he helped shape one of the most spectacular failures in music history.
02:55Fyre Festival was marketed as an ultra-luxurious getaway with good music, gorgeous villas, gourmet food, expensive yachts, and famous influencers partying in paradise.
03:06What attendees actually got was disaster relief tents, wet mattresses, canceled concerts, and cheese sandwiches.
03:15Instead of launching a lifestyle empire, the event launched news reports, documentaries, and numerous lawsuits that turned Ja Rule into a running joke.
03:24He was eventually cleared of all wrongdoing, but his reputation went up in flames.
03:29I remember I first heard about Fyre Festival at a music festival conference in Las Vegas.
03:34Ja Rule was a keynote speaker, and he unveiled this festival that they were going to do in the Bahamas, and everyone at the table I was sitting with just started laughing.
03:43They were like, yeah, good luck, Ja Rule. Like, build a music festival, because it's so easy.
03:47Number 17. U2 forces their album onto everyone's iTunes.
03:54Even if you're not big into following Apple news, most people might now have heard about the new iPhone 6 models and the Apple Watch, but not everyone was aware of one smaller detail in Apple's announcement.
04:06In 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.
04:16The world woke up, checked their phones, and wondered why an album they didn't buy or even want was suddenly taking up space.
04:23While 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.
04:32Privacy concerns exploded, memes flooded the internet, and Apple had to release a special tool just to delete the album.
04:40And you know, maybe the backlash wouldn't have been so bad if this was another Joshua Tree or Octoom Baby.
04:48It was not.
04:49Look, if anyone, you know, wanted a cold time on us, we've been around a while and we just wanted to do something fresh, something that no one else had done.
04:54And you know, it turns out, some people don't believe in Father Christmas.
04:59When they see Father Christmas in their lounge on Christmas morning, they just want to give Father Christmas a good kicking.
05:09Good kicking.
05:10Number 16.
05:11Drake comes after Kendrick.
05:13Trying to strike a chord in his Polly A minor.
05:18Drake just can't stop losing.
05:21It's almost sad at this point.
05:23His diss track, Duppy Freestyle, caused Pusha T to release the story of Ididon, revealing that Drake had a secret son and arguing that he appropriates black culture.
05:33So Drake lost that one.
05:35And then he went after Kendrick Lamar, following a series of increasingly personal disses.
05:41Kendrick released both Meet the Grams and Not Like Us, both of which effectively killed Drake in the public perception.
05:48Drake sulked away and sued Universal for releasing the song.
05:52Kendrick won five Grammys for Not Like Us and played it at the Super Bowl.
05:56By this point, we could only think of that famous Simpsons meme.
06:00Stop.
06:01Stop.
06:02He's already dead.
06:03Stop.
06:04Stop.
06:05He's already dead.
06:07Number 15.
06:08Prince changes his name to a symbol.
06:11The Prince love symbol was revealed for the first time this morning.
06:15That symbol was created in the early 90s that would become part of his legacy for really the rest of his life.
06:21In the 90s, Prince waged war against his record label by changing his name to a symbol.
06:26Unpronounceable by human tongues, although it went by the name Love Symbol.
06:31As political statements go, pretty bold.
06:34As for branding, a bit of a nightmare.
06:37Fans didn't know what to call him.
06:39Journalists needed special fonts, and the media just ignored the statement by calling
06:44him the artist formerly known as Prince.
06:47And his sales plummeted.
06:48After adopting the stage name in 1993, he never again had a top 5 studio album.
06:54And only one of 11 reached the top 10.
06:57It wasn't until Musicology in 2004 that Prince again reached the top 5.
07:02And probably not coincidentally, after changing his name back to Prince.
07:08Number 14.
07:09Elvis says no to A Star Is Born.
07:16This is one of the greatest what-ifs in music history.
07:22Barbara Streisand personally approached Elvis Presley to play the male lead in the 1976 remake
07:27of A Star Is Born.
07:29Elvis showed great interest and personally met with Streisand, believing it could revive his
07:34career and return him to the big screen after years away.
07:38But Elvis' manager, Colonel Tom Parker, demanded too much money.
07:42So negotiations tanked, and the gig went to Kris Kristofferson.
07:46The film was a huge hit and received four Oscar nominations.
07:50Meanwhile, Elvis went back to Vegas.
07:53His health worsened further, and he died in 1977, at just age 42.
07:58A major potential comeback slipped through his fingers.
08:02And all because his manager couldn't resist playing hardball.
08:12Number 13.
08:13Lou Reed Releases Metal Machine Music.
08:24After leaving the Velvet Underground, Lou Reed seemed poised for a great solo career.
08:29Walk on the Wild Side was a hit, and 1974's Sally Can't Dance was his first top 10 album.
08:36The next year came Metal Machine Music, and that was about it for Reed.
08:41The double album was nothing but screeching guitar feedback.
08:44No melody, no structure, just noise, pushing the limits of human patience for 64 minutes.
08:51Some avant-garde fans called it genius.
08:54Everyone else called it unlistenable.
08:56Critics assumed it was a prank, record stores wanted it off their shelves,
09:00and it was even taken off the market after just three weeks.
09:04The album became a benchmark of awful, and Reed never again had a top 10 album in America.
09:10Number 12.
09:11Billy Squire Releases The Rock Me Tonight Music Video.
09:21Billy Squire was riding high with killer rock hits like The Stroke, until a disastrous music
09:35video sent his career into a nosedive.
09:38In Rock Me Tonight, Squire prances around a neon bedroom wearing pastel shirts and dancing
09:43in ways that hard rock audiences were just not prepared for.
09:47Devoted fans fled in droves, concert sales plummeted, and Squire fired his managers.
09:53Rock culture and music historians now label it as the defining moment that killed his career,
09:58a sentiment that Squire himself agrees with.
10:01Ironically, Rock Me Tonight is also Squire's highest-charting single on the Hot 100.
10:07Now, how many artists can claim that their most successful song is also the one that ruined them forever?
10:1411.
10:15MC Hammer Goes On A Disastrous Spending Spree
10:21MC Hammer Proved That You Can't Touch This Does Not Apply To Debt Collectors.
10:38At the height of his fame, MC Hammer was worth about $70 million.
10:43But he spent it like money was going out of fashion, like hammer pants.
10:48He supported friends and family, which is admirable, but he also hired a personal entourage,
10:54bought thoroughbred racehorses, collected luxury cars, and invested heavily in a mansion
10:59with a price tag worthy of a comic book villain.
11:02Before long, the $70 million was blown, and he was $13 million in debt.
11:08Sales dried up, but his debt did not, and Hammer famously filed for bankruptcy in 1996.
11:14He became the poster child for music industry overspending, proving that even chart-topping fame has its limits.
11:2110.
11:29Stephen Van Zant Quits The E Street Band
11:32Stephen Van Zant joined Bruce Springsteen's E Street Band around the time of Born To Run,
11:44joining the group for their complimentary 1975 tour.
11:47tour. He stayed with the band for years before leaving in 1984 to focus on his solo career.
11:53Bad move. That same year, Springsteen released the enormously popular Born in the USA,
11:59which catapulted both him and the band to superstardom.
12:03While Van Zandt co-produced and played on the record, he did not tour for it,
12:07replaced by Niles Lofgren. Van Zandt told Rolling Stone in 2020 that leaving the band
12:13was a mistake he's never recovered from, and that, financially, it was apocalyptic.
12:19Still, he later found success as Silvio on The Sopranos. So, that's something…
12:25I was just trying to sweep the cheese away from you. Why? Why now? Leave it there!
12:299. Ashley Simpson Decides To Lip Sync On SNL
12:34Once again, Ashley Simpson.
12:46On a Monday, I'm waiting. Tuesday, I'm fading.
12:51Ashley Simpson was on the rise in the early 2000s, with her debut album,
12:55Autobiography, being a big hit. And then came the legendary night of October 23, 2004.
13:02Simpson supposedly had acid reflux that night, so she decided to lip-sync her performance on SNL.
13:08And when the wrong vocal tracks started playing, the singer froze, did a funny hoedown, and awkwardly
13:14jiggered her way offstage. Millions watched the moment live, instantly turning her from an up-and-comer
13:22to a national punchline. It was viral before viral was even a thing, and, you know, it wouldn't be so
13:28bad if she didn't blame her band. But she did, and it was momentous, and it put a permanent stain on
13:35Simpson's professional reputation.
13:37Ladies and gentlemen, what can I say? Live TV?
13:40Exactly! I feel so bad my band started playing the wrong song, and I didn't know what to do,
13:44so I thought I'd do a hoedown.
13:468. Guns N' Roses Keep Delaying Chinese Democracy
13:57You know what really kills a career? A 15-year gap between projects. Guns N' Roses were once
14:03the coolest band in the world, but their career hit a brick wall in the early 90s following
14:08the spaghetti incident. The band's follow-up Chinese democracy became Rose's personal obsession,
14:14so much so that it would take over a decade to create. The album was plagued by constant rewrites,
14:20rotating band members, relentless infighting, and a ballooning production budget that eventually exceeded
14:2613 million dollars. And when the album finally arrived in 2008, it was met with a collective
14:32meh. It sold well, but few cared for the music, and the band's reputation remained stuck in the 90s.
14:477. Garth Brooks Becomes Chris Gaines
14:51In 1999, country megastar Garth Brooks decided to reinvent himself as Chris Gaines, an Australian
15:05rock star with emo hair and a soul patch. It was bewildering. Brooks had big plans for Chris,
15:12including a fictional biopic, and he appeared as Gaines in a Saturday Night Live episode that he was
15:17hosting as himself. But the mainstream public had little interest in this Chris Gaines fella,
15:22and Brooks fans didn't want their cowboy god looking like he was cosplaying Professor Snape.
15:28Despite a hit song with Lost in You, the Gaines character was a huge flop and the movie was
15:33cancelled before it even began. The curious experiment has gone down as perhaps the most
15:38baffling identity crisis in music history.
15:42Chrissy, I hate to tell you this. I know, I know. Garth is Chris Gaines. You really think I'm stupid,
15:47don't you? I mean, did you hear the album? No. That's what I'm saying. It's crazy, man. I just can't
15:53believe he did that album. These are strange times.
15:576. Milli Vanilli fake their entire career. On the front page, one day after it was revealed that the pop
16:05duo Milli Vanilli didn't sing on their hit album, few in the music industry are surprised, but many did
16:11not realize the extent of the deception. This R&B duo had it all. Chart-topping hits, Grammys,
16:17and the coolest jackets of 1989. Then a disastrous live performance exposed the truth. The duo wasn't
16:24actually singing. In fact, they never were singing. Following the infamous MTV fiasco, the band's producer
16:32Frank Farian announced that the vocals actually belonged to different studio singers, not
16:37Fab Morvan and Rob Pilatus. The Grammy was revoked, their careers collapsed overnight, and they
16:43tried to save face by making them sing for real. But that only made things worse.
16:48So instead of being remembered for catchy pop perfection, Milli Vanilli became the universal
16:53shorthand for musical fraud. 5. Simon Cowell passes on the Spice Girls
17:12Simon Cowell is known for spotting pop gold, but even the best talent scouts miss a few opportunities.
17:18Legend has it that the Spice Girls gave an impromptu audition to Cowell in a parking lot.
17:23But the music mogul wasn't impressed and turned them down. Cowell says otherwise, claiming they
17:29rejected his offer. Either way, a deal was not made, and these random people off the streets soon
17:35became the biggest girl group on the planet, selling millions of records and launching a global cultural
17:41phenomenon. Cowell later admitted that letting them go was the biggest regret of his career. Instead of
17:47riding the Spice Hype train all the way to the bank, he watched from the platform as the girls
17:52revolutionized pop.
17:53I need some love like I never needed love before. Wanna make love to ya.
18:014. Kanye West interrupts Taylor Swift at the VMAs
18:05Yo, Taylor, I'm really happy for you. I'ma let you finish. But Beyoncé had one of the best videos of all time.
18:13You know, looking back, it was all downhill from here. The 2009 VMAs were going smoothly until Kanye
18:20West stormed the stage, grabbed Taylor Swift's mic, and declared that Beyoncé should have won instead.
18:27The audience booed, the internet exploded, and a massive cultural storm was born. Kanye was already
18:34known for being unpredictable and eccentric, but it was this moment that catapulted him into full-on
18:40jerk territory, and he hasn't really let up since. Taylor's shocked reaction became iconic, Beyoncé
18:47looked uncomfortable as all heck, and Kanye's reputation took a major, permanent hit. If he never
18:54stormed this stage and turned himself into a troll, who knows what the future would have held.
19:00I ain't saying she a gold digger, but she ain't messing with no bro, bro.
19:043. Metallica sues Napster
19:08And then we were sort of like a little bit like deer caught in headlights, and then obviously we
19:13stood our ground and fought the fight. But obviously it was, I mean, it was a difficult time. I mean,
19:18it's not easy being finger whacked at that level. Metallica helped define the heavy metal rebellion
19:25and then stopped their fans from sharing their music. Now how metal is that? When Napster made
19:31file sharing popular in the early 2000s, Metallica became the face of the anti-piracy crackdown.
19:37Their arguments about protecting artists' rights weren't wrong per se, but the optics were absolutely
19:43brutal. Late night shows mocked them endlessly. Lars Ulrich became a meme, and fans accused them of
19:50being greedy and selling out to their corporate overlords. The lawsuit helped shut Napster down,
19:55but damaged Metallica's cool factor for good. It wasn't a great PR move for a band once seen as the
20:01voice of the people in the downtrodden. Even today, Metallica is still known as the band that sued Napster.
20:08Look, there's Lars now sitting by his pool. What's the matter with him? This month he was hoping to
20:15have a gold-plated shark tank bar installed right next to the pool. But thanks to people downloading
20:19his music for free, he must now wait a few months before he can afford it. Number two,
20:25the Beatles hire Alan Klein. It was bad enough that all that money we'd earned and all that fame was going
20:33down the pan. And there was this guy who was going to take it all. And it was that close. And I was
20:39having to fight and say, no guys, we can keep it. We don't have to give it to this guy, you know.
20:46There are countless reasons as to why the Beatles broke up, but a big one was Alan Klein.
20:52In their final tension-filled years, the Beatles couldn't even agree on management. Paul wanted Lee
20:58Eastman, a respected business mind, and conveniently his future father-in-law. The rest chose Alan Klein,
21:06a music manager with a reputation bordering on professional chaos agent. Klein pushed aggressive
21:12financial tactics which strained already strained relationships to their breaking point and
21:17accelerated the group's breakup. Years later, accusations of mismanagement piled up, along with
21:24some lawsuits. Yes, the Beatles already had internal issues, but everything collapsed once
21:29Klein took control of Apple.
21:391. The Rolling Stones Hired The Hells Angels
21:59for Altamonts.
22:09Numerous things are blamed for ending the 60s, and the Altamont Free Concert is one of them.
22:15Trying to recreate Woodstock on the West Coast, the Rolling Stones hosted the concert, and reportedly
22:21allowed their management to hire the Hells Angels as security, and paid them in beer. It was a disaster
22:27waiting to happen. The environment soon became dangerous, with countless people being injured,
22:32one drowning in a canal, and two being killed in a hit-and-run. And then, of course, there was
22:38the death of Meredith Hunter, stabbed and killed by Hells Angel, Alan Pissarro. Instead of delivering a
22:45harmonious moment of counterculture peace and love, Altamont became a horrifying cautionary tale of violence.
22:50Rock and roll may celebrate rebellion, but hiring actual outlaws was a little too on the nose.
22:58What do you make of these decisions?
23:11Right call or no?
23:13Let us know in the comments below!
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