Vol. 26: Can the Artist Become Bigger Than the Machine?

Six incredible stories of musicians who challenged the industry that helped make them stars.

The music business is built around creating stars.

Record companies spend enormous amounts of money finding artists, recording albums, promoting them, distributing their music and trying to turn an unknown musician into someone millions of people will pay to hear.

Most of those bets don't become superstars.

But every once in a while, it works almost too well.

The artist who once desperately needed the record company suddenly has millions of fans. Their albums sell millions of copies. Their tours sell out arenas. Their catalogue becomes worth a fortune.

And eventually, some of them start asking uncomfortable questions.

Why don't I own my recordings?

Why can't I release an album when I want?

Why can someone else tell me what my music is supposed to sound like?

Why do I need your ticketing system?

And, eventually:

Who needs who more now?

That's when things can get interesting.

Because while the music industry wants successful artists, success creates leverage. And when an artist decides to use that leverage, the relationship between artist and industry can change very quickly.

Here are six examples of what happened when some of music's biggest artists decided to challenge the machine.

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TOM PETTY: REFUSE

In 1979, Tom Petty declared bankruptcy.

Not because nobody wanted his music.

Almost the opposite.

Petty and the Heartbreakers had originally signed with Shelter Records. When Shelter's parent company was acquired by MCA, Petty discovered that his recording contract was effectively part of the transaction.

He wasn't interested.

Petty objected to the idea that he could essentially be bought and sold along with the company.

So he refused to deliver his next album.

MCA maintained that Petty was still under contract. Petty financed the recording himself. His debts reportedly climbed to around $500,000.

Then he played his biggest card.

He filed for bankruptcy.

The move put his contracts into question and gave Petty an opportunity to force the issue.

Eventually, MCA blinked.

The company released Petty from the existing agreement and then promptly signed him to a new deal reportedly worth $3 million through a newly created subsidiary.

And the album Petty had been refusing to hand over?

Damn the Torpedoes.

It became the breakthrough that turned Tom Petty and the Heartbreakers into superstars.

But Petty wasn't finished fighting.

Two years later, MCA wanted to introduce what became known as “superstar pricing” for his next album, Hard Promises. Instead of the usual $8.98, the company wanted to charge $9.98.

One dollar doesn't sound like much today.

To Petty, that wasn't the point.

He believed his fans were being asked to pay more simply because he had become successful enough that MCA thought they would.

So Petty threatened to withhold the album again. He even considered calling it $8.98.

MCA backed down.

Hard Promises sold for $8.98.

The first time Petty challenged the machine, he was fighting for control of his own career.

The success that followed gave him enough power to challenge it again — this time over what his fans should have to pay.

Petty had learned something important.

Once an artist becomes valuable enough, saying no starts carrying considerably more weight.

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PRINCE: REBEL

SLAVE.

Prince began appearing in public with the word written across his face.

To understand why one of the most successful musicians on earth would describe himself that way, you have to understand what Prince believed success should have earned him.

Control.

Prince was extraordinarily prolific. He recorded constantly and wanted to release music at a pace that Warner Bros. believed could ultimately hurt the commercial performance of his own records.

From the record company's perspective, there was logic to that.

Albums needed time to be promoted. Singles needed time at radio. Tours supported records. Flooding the marketplace with Prince albums risked having one Prince record competing against another.

Warner believed it was protecting the Prince business.

There was just one problem.

Prince believed the Prince business belonged to Prince.

The disagreement became increasingly bitter.

In 1993, Prince stopped using the name Prince professionally and instead adopted the unpronounceable symbol that combined the male and female gender symbols.

For years, he became “The Artist Formerly Known as Prince.”

It can be remembered now as one of Prince's many eccentricities.

But it really wasn't. There was much more to it than that.

Prince's argument was that Warner controlled the music released under the name Prince. If that was the case, he would simply stop being Prince.

He also began rapidly delivering albums to satisfy his remaining contractual obligations.

It was one of the strangest and most public artist-versus-record-company battles the industry had ever seen.

Who actually owns the music?

Underneath the symbol and the word SLAVE was a question that would become increasingly important for artists in the decades that followed:

Who actually owns the music?

Prince would later summarize his philosophy perfectly:

“If you don't own your masters, your master owns you.”

Eventually, the story came full circle.

Nearly two decades after their bitter split, Prince and Warner Bros. reached a new agreement in 2014 that returned ownership of his classic Warner-era master recordings to him.

The artist who once wrote SLAVE across his face had finally gained control over the music at the centre of the fight.

But ownership wasn't the only thing a record company could try to control.

Sometimes it was the definition of the artist himself.

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NEIL YOUNG: DEFY

In 1983, Neil Young's record company sued Neil Young for making records that didn't sound enough like Neil Young.

Yes, really.

Young had left his longtime label Reprise and signed with David Geffen's newly established Geffen Records.

The label had landed Neil Young.

What it apparently expected in return were Neil Young records.

Then Young delivered Trans.

The album leaned heavily into synthesizers, electronic sounds and vocoders that distorted Young's familiar voice.

It wasn't exactly Harvest.

Then came Everybody's Rockin', a short, deliberately retro rockabilly album recorded with a band Young called the Shocking Pinks.

Geffen had had enough.

In 1983, the company sued Young for more than $3 million.

Among its complaints was the extraordinary claim that the albums Young was delivering were not commercially viable and were “musically uncharacteristic” of Neil Young's previous recordings.

Neil Young wasn't Neil Young enough?

Think about that for a moment.

A record company had signed Neil Young.

Neil Young made some records.

And the company sued him because the Neil Young records weren't Neil Young enough.

Young countersued.

There is something almost philosophical hiding underneath the absurdity.

A record company investing millions of dollars in Neil Young understandably expects to receive music that people who like Neil Young might want to buy.

But from the artist's perspective, there's an equally compelling argument.

If Neil Young made it, isn't it — by definition — Neil Young music?

When a company signs an artist, is it investing in that artist's creativity?

Or is it purchasing an expectation of what that creativity is supposed to produce?

Eventually, the lawsuits were dropped.

Neil Young kept doing what Neil Young has pretty much always done, which is, whatever Neil Young wanted to do.

But if Neil Young's battle showed how much influence a record company could attempt to exert over an artist's music, Pearl Jam was about to discover something else.

The record company wasn't necessarily the most powerful machine in the music business.

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PEARL JAM: FIGHT

In the mid-1990s, Pearl Jam was one of the biggest bands in America.

Then they decided that they didn't need Ticketmaster.

The dispute began over ticket prices and service fees.

Pearl Jam wanted to keep ticket prices relatively low and objected to the additional charges Ticketmaster was adding.

So the band decided to do something about it.

Pearl Jam filed an antitrust complaint against Ticketmaster with the U.S. Justice Department.

Stone Gossard and Jeff Ament went to Washington and testified before Congress.

And then the band attempted something even more ambitious.

Pearl Jam tried to tour without Ticketmaster.

That sounds relatively straightforward until you consider how deeply Ticketmaster was embedded in the infrastructure required to put on a major American concert tour.

Many of the venues capable of holding a Pearl Jam-sized audience had relationships with Ticketmaster.

So Pearl Jam began looking elsewhere.

Alternative venues.

Outdoor sites.

Alternative ticketing arrangements.

At points, even mail-order ticket lotteries.

Keep in mind, this wasn't some unknown punk band trying to put together a DIY club tour.

This was one of the biggest rock bands in North America trying to prove that it could operate outside the industry norm. I mean, everyone used Ticketmaster.

And after more than a year of trying, Pearl Jam reached an uncomfortable conclusion.

It couldn't.

And that was exactly the point.

The band's manager, Kelly Curtis, eventually acknowledged that under the circumstances it was effectively impossible for a major rock group to mount a normal national tour without Ticketmaster.

Which made for an interesting end to the fight.

Pearl Jam had tried to prove that Ticketmaster had too much control over the concert business.

Ticketmaster survived the challenge.

The Justice Department eventually closed its investigation without taking action against the company.

And Pearl Jam's attempt to operate outside Ticketmaster had largely failed.

But Pearl Jam could point to that failure and say:

Exactly. That's our point.

Sometimes an artist can become one of the biggest acts in music and still discover that the infrastructure surrounding them is even bigger.

Sometimes the artist challenges the machine.

And sometimes the machine wins.

For decades, that was one of the fundamental problems facing musicians who wanted independence.

You could fight your record company.

You could fight the ticketing company.

But eventually you still needed someone to manufacture, distribute, promote or sell your music.

Then something changed.

The internet arrived.

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FRANK OCEAN: OUTSMART

August 19, 2016.

After years of waiting for another Frank Ocean album, fans finally got one.

Ocean released the visual album Endless through the record label, Def Jam.

Then, almost immediately afterward, he dropped another album called Blonde — without any involvement or association with Def Jam.

It was the culmination of what Ocean would later describe as a “seven-year chess game.”

His relationship with Def Jam had become strained over the years, but by 2016 Ocean had finally found his way out of the deal.

Endless satisfied his remaining contractual obligation.

Then came Blonde.

The album everybody had really been waiting for.

And this time, Frank Ocean owned it.

Even without Def Jam's involvement, Blonde debuted at No. 1.

A quick side note about my copy of Blond

Side note: I actually own an original 2016 Black Friday vinyl pressing of this album. It's one of the more valuable records in my collection.

And in researching this article, I realized I've been mistaken about something for a long time.

The album is called Blonde.

But look at my copy and the cover says:

Blond.

For years, I assumed it was a mistake.

I thought someone had somehow managed to misspell the album title on the vinyl cover, and that explained why the record was only available for 24 hours on Black Friday 2016.

Turns out I was wrong.

The different spelling was intentional. Ocean used both Blonde and Blond around the project. The album is generally known as Blonde, while the original vinyl release shows Blond on the cover. The use of both spellings has often been interpreted as another expression of the duality running through the album.

And that 24-hour sale?

It wasn't a frantic attempt to get a typo off the market.

The vinyl really was offered for only 24 hours through Ocean's website on Black Friday 2016.

So, after owning the record all these years, researching DMM Vol. 26 managed to teach me something about my own collection.

He found the exit.

But the record also represents something bigger in this story.

Tom Petty needed bankruptcy.

Prince spent years publicly battling Warner.

Pearl Jam discovered how difficult it was to construct an alternative to Ticketmaster.

Frank Ocean didn't defeat the machine.

He figured out where the exit was.

Technology had fundamentally changed the equation.

An artist could now reach millions of listeners without necessarily needing the same infrastructure artists had relied upon for decades.

That didn't make record companies irrelevant.

Far from it.

But the machine was no longer the only machine.

And that brings us to today.

Because artists may now have more ways to reach their audiences than ever before.

But the companies behind the world's biggest music have also become enormous.

Which brings us to Drake.

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DRAKE: CONFRONT

Drake isn't simply one of the world's most streamed artists.

He is an extraordinarily valuable music business.

In 2022, details emerged of a massive deal between Drake and Universal Music Group covering recorded music, publishing, merchandise and other parts of his business.

Industry sources reportedly valued the arrangement at $400 million or more.

At the time, estimates suggested Drake's music alone could be generating around $50 million annually. And that doesn't include his many endorsement deals and side projects.

That's important context for what came next.

Because this isn't really a David-versus-Goliath story.

It's one extremely valuable artist confronting one extremely powerful corporation.

Then came Kendrick Lamar.

In 2024, Drake and Kendrick Lamar became involved in one of the biggest rap battles in years, exchanging increasingly personal diss tracks.

Then Kendrick released Not Like Us.

Among other attacks, the song repeatedly portrayed Drake as a sexual predator and included the now-famous line referring to him as a “certified pedophile.”

The record became enormous.

It topped the charts, won multiple Grammys and turned what had begun as a rap battle into a global pop-culture event.

But Drake's next move wasn't another diss record.

In January 2025, he sued Universal Music Group — the company behind his own music as well as the company involved in distributing Kendrick Lamar's.

Drake did not sue Lamar.

Instead, he alleged that UMG knowingly published and aggressively promoted Not Like Us despite what he argued were false and defamatory accusations contained in the song.

UMG denied the allegations and argued, among other things, that Drake had participated willingly in a rap battle in which both artists hurled extreme accusations at one another.

Had Drake become too valuable?

But there is another part of Drake's argument that is particularly interesting in the context of everything we've been talking about.

Drake alleged that UMG had an economic incentive to diminish the value of his brand ahead of future contract negotiations.

Think about that.

One of the world's most commercially valuable artists was essentially arguing that becoming enormously valuable to the machine had itself created a new source of tension with the machine.

UMG's response raises an obvious question:

Why would it intentionally damage one of its most valuable assets?

The company has invested heavily in Drake and makes a lot of money when Drake succeeds.

Those two positions get right to the heart of this entire article.

Drake's lawsuit was dismissed by a federal judge in October 2025.

The judge ruled that, viewed in the context of an escalating rap battle, the disputed statements in Not Like Us amounted to nonactionable opinion rather than statements that a reasonable listener would interpret as verifiable facts.

Drake appealed.

And as I write this, the story isn't finished.

Which makes Drake different from everyone else we've talked about.

We know how Petty's fight ended.

We know what happened with Prince.

We know Neil Young kept making whatever he wanted.

We know Pearl Jam eventually abandoned its attempt to tour without Ticketmaster.

We know Frank Ocean walked away and released Blonde independently.

With Drake, we're watching the relationship between artist and machine being tested right now.

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WHO NEEDS WHO?

It's tempting to tell these stories as brave artists fighting evil corporations, but I don't think it's that simple.

Record companies take risks. They invest money in artists who may never sell enough records to recover that investment. They provide marketing, distribution and infrastructure that can help turn musicians into global stars.

And when an artist signs a contract, the company understandably expects that contract to mean something.

But occasionally the bet pays off beyond anyone's imagination.

The artist who once needed the machine suddenly has something the machine needs too:

the audience.

And that changes things.

Petty fought his contract.

Prince fought for ownership and control.

Neil Young fought for the right to sound like whatever version of Neil Young he wanted to be.

Pearl Jam tried to bypass an industry gatekeeper and discovered just how powerful that gatekeeper was.

Frank Ocean found another way out.

And Drake's fight is still happening.

The music business wants to create stars.

But the bigger those stars become, the more leverage they have.

And maybe that's the irony in all of this.

The machine spends millions trying to create artists powerful enough to reach the entire world.

Then one day, those artists may become powerful enough to ask:

Who really needs who?

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