July 17, 2019 / 5:30 PM

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Biggest Contracts in Music History: Jay Z, Lil Wayne, Michael Jackson and More



Stevie Wonder struck it rich 40 years ago on this day when he signed what was, at that point in history, the most lucrative music contract ever: $13 million for seven years and seven albums for Motown/Tamla Records. Granted, things have gotten bigger in the four decades since—both in terms of payouts and inflation rates. Here are the five biggest contracts signed in music history, not adjusted for inflation. Understand that many of these deals won't ever be surpassed due to the increasingly smaller likelihood that a performer or band will sign for such lengthy periods. Jay Z, Lil Wayne and more cash in:

05) Bruce Springsteen and Columbia Recordings = $150 million (2005)

There's always a risk when considering what kind of money to offer music legends. On one hand, Bruce Springsteen is one of the biggest names in music, but that's almost entirely based on his discography up until this point. If he puts out another record, will it bring in the kind of money that Columbia is considering putting into it? Consider that The Rolling Stones entered its loathed '80s recording period after signing the then-biggest contract of all time with CBS, and Virgin ended up paying Mariah Carey to axe the massive contract it signed with her prior to Glitter's failure. So far, it seems that Columbia made the right move by offering one of the largest contracts ever to The Boss: All five of the albums that he and The E Street Band have released since signing the megadeal have gone to no. 1 on the Billboard 200.

04) Jay Z and Live Nation = $150 million (2008)

Hov may only be at no. 5 overall on this list, but he also secured one of the most solid deals from a personal standpoint: Not only was Live Nation paying him $150 million, it was so that he could release his music on his own imprint, Roc Nation. Of course, Live Nation was getting a lot more than albums for its massive deal with the biggest name in hip-hop at the time-in fact, Jay was "only" getting paid $10 million for three expected albums over ten years. The rest of his paycheck came as a result of exclusively using Live Nation for his tours and business deals for the 10-year period (what's called a "360 deal," encompassing the act's entire profitable identity, essentially). Pitchfork headlined its summary of the deal at the time by saying "Jay-Z signs with Live Nation for a Bazillion Dollars." Live Nation was on a heck of a spending spree during 2008, coughing up $120 million to handle Madonna's career, and a deal with U2 worth a similar amount.

03) Lil Wayne and Cash Money Entertainment = $150 million (2012)

One of the most popular music stories of 2015 is tied to Lil Wayne's attempts to leave the Cash Money label because of its hesitation in releasing The Carter V, and Weezy's lawsuit against the label for refusing to let him go. That kind of set up might lead you to think that Wayne is the 100 percent victim here...but it's not quite true. Going back a short way to 2012, we see that Cash Money realized it would have to shell out to keep one of the biggest names in hip-hop from leaving for a more major label. Birdman and company offered him $150 million for four albums, which was the deal Wayne reported at the time. We have no idea why Cash Money is allegedly sitting on a new Carter title. But up to this point, if it drops that album, Wayne will still owe the label two more before he can split (as the Free Weezy Album was released on Tidal without Cash Money's consent). On one hand, Cash Money owes Wayne for bringing profit-machine Drake under the label's umbrella, but then again, Wayne probably owes Birdman for his career. Money doesn't solve everything.

02) U2 and Polydor = $200 million (1993)

It would be logical to expect, after three $150 million deals, that the next biggest entry on the list would occur more recently than 22 years ago. Although U2 may still hold the title for the "biggest band in the world," it truly has nothing on the massive sales/critical successes the band experienced with The Joshua Tree and Achtung Baby. Polydor, the owner of Island—the label that U2 released its biggest hits on—was certain that the band could do so again, so it offered the band $200 million to stick with the label. The move wasn't a bad one, necessarily, from a record label's point of view: The following albums both went to the top of the sales charts. Zooropa (1993) and Pop (1997) are generally considered among the worst of the band's releases. Fortunately the band got back on the quality wagon as well for 2000's All That You Can't Leave Behind.

01) Michael Jackson and Sony Music = $250 million (2010)

You may have raised an eyebrow when you saw the date at which point "Michael Jackson" inked his record-breaking deal with Sony Music...more than a year after his death. The contract was actually negotiated between his estate and Sony. One could say that the label was being rather cynical, but numbers don't lie: The King of Pop's catalogue had sold more than 31 million albums in the 12 months following his death and Sony wanted to ensure that it was still the label that was reaping the benefits for the next seven years (the deal will probably be renegotiated during 2017). The deal also involved plans to release ten albums—consisting of both hits compilations and rereleases of classics such as Thriller—but also a few collections of new music, which we've seen in Michael and Xscape. Sony also got the benefit of benefitting from productions such as Cirque de Soleil's ONE project. That's about the best testament you can give for Jackson's role in music history...Sony paid $250 million for the almost-guarantee of no new music.

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