10 of The biggest music deals ever signed by Artists

Moon Walker


We all have a favorite artist whom we just can’t stop listening to their music or buying their concert tickets or merchandise. And even though most artists create music because they have the talent and the passion, they also got to make a living.

Below are 10 of the biggest deals ever signed by music artists.

Michael Jackson — $250 million 

Michael JacksonThe Independent

Does it surprise anyone that Michael is number 1? He’s sold over an estimated 350 million records worldwide! His sixth studio album that he released in 1982, Thriller, remains the best-selling album ever! It’s been sold over 66 million times! What else could an artist ask for? For Michael, that meant big checks even if he isn’t around. 

In 2010, Sony Music Entertainment entered into a deal with the singer’s estate — the biggest record deal ever. For $250 million dollars, Sony got the rights for 7 years to make money off of Michael’s entire music catalog!

U2 — $200 million 

U2Rolling stone

Since their debut in the 70s, U2 has released 14 studio albums and sold around 170 million records around the world. That makes them one of the best-selling artists ever. 

They’ve also won a record 22 Grammy Awards, more than any band in history! The 90s was U2’s biggest decade. Their 1991 album Achtung Baby was one of their biggest albums, both in terms of earnings and the influence it had in the music world. The album’s success was followed up by the Zoo TV Tour from 1992 to 1993. And just like Achtung Baby, the tour pulled in some impressive numbers. It was the highest-grossing North American tour at that time. 

In 1993, U2 signed a 10-year deal with their then record label Island Records. For a whopping $200 million dollars, the record label acquired rights to both the band’s next six albums and their entire catalog! That huge dollar sum made U2 one of the most paid rock bands even to this day.

Lil Wayne — $150 million


Lil WaynePage 2

Lil Wayne had a successful long-term career with Cash Money Records, his very first record label. Aside from his own success, he’s also credited with bringing Drake and Nicki Minaj into the label. That’s something that definitely paid off big time for Cash Money’s founder, Birdman. So it’s only natural that Birdman wasn’t willing to let Lil Wayne go just yet. 

In 2012, the Cash Money Record founder announced that Lil Wayne had signed what he called the biggest deal ever in rap music. The deal was worth an estimated $150 million and covered four more albums with the record label. Birdman acknowledged Lil Wayne’s immense contribution in making Cash Money a big name in the music industry. He told MTV awards that there wasn’t much of the label without Wayne’s input. 

But to make a really long story really short, Cash Money and Lil Wayne had big disputes. Cash Money wouldn’t let Lil Wayne release numerous projects, such as The Carter 5. They eventually completely called it quits in 2018. Who knows how much money Lil Wayne actually saw from that deal!

Jay Z — $150 million

Jay ZBlack Enterprise


Jay Z was another big artist to get a lucrative deal from Live Nation. This mega-deal came just a year after Madonna inked her deal! Jay-Z’s deal covered 3 albums over 10 years and he was getting a $10 million dollar advance payout for each one. 

Other contract terms included $25 million upfront payment, $20 million for publishing and licensing rights, and $25 million overhead for five years. 

Back in 1995, no major record labels would give Jay Z a deal so he sold his early music out of his car. That same year, he went on to launch Roc-A-Fella label together with Damon Dash and Kareem Burke. 

Amazingly, in 2017, Jay signed a 200 million dollar touring deal over 10 years with Live Nation as well!

Bruce Springsteen — $150 million 

Bruce SpringsteenUSA Today

Bruce got some recognition earlier on in his career in the 70s with the release of his debut album, Born to Run. But his ultimate win came several years later with the release of Born in the U.S.A. The album is Springsteen’s most successful with at least 30 million copies sold worldwide. It’s easily one of the best-selling albums of all time. He followed it up with a few others such as Tunnel of Love, Human Touch, and Lucky Town among others. 

Beyond the albums and tours, probably his career highlight was in 2005 when he signed a whopping $150 million dollar deal with Columbia Records. There’s not much on the exact details. But we can guess the label probably still got a good deal as Springsteen is still pulling in impressive numbers!

Adele — $130 million 

AdeleVanity Fair

Adele has been breaking and setting records ever since she released her debut album in 2008. That album achieved multiple platinum sales both in the UK and US, propelling her to top music status early on in her career. Her second album further built on her established legacy with record sales and won her music awards all over. That album called 21 scooped six Grammy Awards — making Adele the only other artist apart from Beyonce to achieve such a feat. 

The album also has a cumulative sales record of 31 million copies worldwide, the highest count so far this century for a single album! She took a four-year break and in 2015, she came back with yet another successful album going by the name 25. 

But in the same year, her deal with XL Records had come to an end. This means she was free for a new signing. So Sony Music grabbed the opportunity to offer her a $130 million dollar deal, setting a new milestone in Adele’s decorated music career. This deal meant that Adele had broken the record for the most expensive deal ever signed by a female artist, beating both Madonna and Whitney Houston.

Robbie Williams — $125 million 

Robbie WilliamsMusic Week

Robbie Williams’ 2001 £80 million deal with EMI is the 2nd biggest record deal ever in history for a British artist. That basically translated to $125 million back then. 

Robbie Williams launched his solo career in 1996, and it was a bit unlikely he was going to land the biggest UK deal ever at that time. His first single titled Before I Die didn’t perform well in other countries but managed a second position in UK charts. It took his fourth single Angels to gain a foothold in the larger European music scene. More success followed with his second album, I’ve Been Expecting You in 1998 with over 3 million copies sold in the UK alone. 

A few years later, he landed the £80 million deal giving EMI rights over subsequent recordings, tours, publications, and merchandise. The deal included a £10 million pound advance, £15 million pounds for the first album, and £55 million pounds for the remaining 3 albums.

Madonna — $120 million 

MadonnaDaily Mail

Madonna holds the highest sales for tour tickets with a record of $1.4 billion dollars. This makes her the highest-grossing solo touring artist ever. She also has sold over three hundred million albums! 

Do we need to say she’s among the best-selling artists of all time? So it’s pretty easy to see that she’s been landing big deals since the 1990s. 

Her first major deal was in 1996 when she got a $60 million dollar contract with Time Warner and an additional 20% in royalties. Her second big deal was in 2007 with Live Nation worth $120 million. In the 10-year deal, Madonna got a $17.5 million advance and another $50 million in cash and stock.

Whitney Houston —  $100 million


Whitney HoustonPitchfork

Whitney Houston holds the Guinness World Record for the most number of awards won for a female artist ever, with around 600 awards. The record was awarded in 2006 and it was just icing on her already accomplished music and acting career. 

As a singer and songwriter, she already had major milestones including millions of album sales worldwide and had several of her tracks on the Billboard Hot 100. 

Back in the late 90s, she was already the best-selling artist of her label Arista. At that point in 2001, she had sold more than 140 million records worldwide since 1983! So it was only natural that they’ll try to retain her. Arista reached a $100 million dollar deal with Whitney. The full details of the deal weren’t made public, but we do know that she had to deliver 6 albums, and she also got royalties per sale.

Prince — $100 million 


With over 130 million record sales worldwide, Prince was no doubt one of the best-selling artists in history. Sales aside, he was also known for the prolific amount of music he made over his career. 

At the time of his death in 2016, he had released around 39 albums give or take! He also had unreleased projects at his home stored away in a vault! This work ethic was probably the reason why Warner Bros was willing to extend an earlier contract at the hefty sum of $100 million in 1992. The amount came as a huge surprise since it was way more than the biggest pop icons at that time. 

Prince was slated to receive a $10 million dollar advance per album, and he would get between 20–25% in royalties. While the royalty was unconditional, the advance wasn’t. For him to keep the $10 million dollars advance, he had to sell over 5 million albums to keep it! And, Prince didn’t get any guaranteed money in this deal.

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Jack is a freelance writer and editor who loves to inspire others with his words and also share interesting stories to the world.

New York City, NY

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