Name: Top 20 Worst Decisions in Music History
Uploaded: 2025-12-05T17:04:39.000Z
Duration: 23 min 20 s
Description: Thousands of YouTube videos with English-Chinese subtitles! Now you can learn to understand native speakers, expand your vocabulary, and improve your pronunciation...

today we're counting down our picks for the most disastrous financial and creative decisions in music history.

We have a comment from one of our producers, Ricky Camilleri, saying, does Lars regret the way in which he handled Napster back in the day?

Number 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 Grail Marcus summed up everyone's thoughts when he opened up his famous review with the question, what is this 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.

You are now about to witness the strength of street knowledge.

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 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.

While NWA 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.

I know it's a lot, but you had to know the truth sometime.

You know, Dre and Cube try to warn me about this.

Ja Rule just called us, basically said he wants us to pitch him for his new app, Fire.

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

What attendees actually got was disaster relief tents, wet mattresses, canceled concerts and 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.

I remember I first heard about Fyre festival at a music festival conference in Las Vegas.

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.

They were like, yeah, good luck, Ja Rule.

Like, build a music festival because it's so easy.

Number 17, U2 forces their album onto everyone's itunes.

Even if you're not big into following Apple news, most people by now have heard about the new iPhone 6 models and the Apple watch.

But not everyone was aware of one single smaller detail in Apple's announcement.

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.

Look, if anyone, you know, wanted to call time on us, we've been around a while, and

we just wanted to do something fresh, something that no one else had done.

And, you know, it turns out some people don't believe in Father Christmas.

When they see Father Christmas in their lounge on Christmas morning, they just want to give Father Christmas a good kicking.

Drake comes after Kendrick trying to strike a chord, and it's probably a minor.

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.

Following a series of increasingly personal disses, Kendrick released both Meet the Grams 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.

The Prince Love Symbol was revealed for the first time this morning that cymbal was created in the early 90s that would become part of his legacy for really the rest of his Life.

In the 90s, Prince waged war against his record label by changing his name to a cymbal unpronounceable by human tongues.

Although it went by the name Love Symbol, as political statements go pretty bold.

the media just ignored the statement by calling him the artist formerly known as Prince, and

After adopting the Stage name in 1993, he never again had a top five studio album, and

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.

Elvis says no to A Star Is Born I'm Esther Hoffman Howard.

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 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.

His health worsened further, and he died in 1977 at just age 42.

A major potential comeback slipped through his fingers, and all because his manager couldn't resist playing hardball.

Subtitles ListPlay Video

Top 20 Worst Decisions in Music History

eventually

permanent

regret

reputation