10. Michael Jackson: $350 million
The King of Pop earned $50 million a year through the 1980s and 1990s.
In 1985, he already had one of the biggest-selling albums ever ("Thriller," which sold 66 million copies worldwide) a series of incredibly lucrative tours, and a record $5 million deal with Pepsi (worth $11 million today) to his name, and the questionable investments started coming quickly.
He dropped $47.5 million to buy ATV Music, which included the Beatles’ catalog (which Paul McCartney would later buy back at a bargain).
In 1987, he bought the “Neverland” ranch for $19.7 million and invested another $35 million in it. By 2003, he held $200 million in debt, but even that wasn’t enough to break him.
9. Jimmy Buffett: $400 million
Buffett has been drawing his faithful Parrotheads and their battery-powered margarita blenders to amphitheaters every summer since 1976. (2011’s tour raked in $22 million).
And if you want an ersatz version of the experience, you might stop in at one of the many locations of Buffett’s Cheeseburger in Paradise chain restaurants, located off an interstate exit near you.
8. Dolly Parton: $450 million
The woman who sang “9 to 5” is worth nearly half a billion dollars, due to a tireless work ethic (she’s written thousands of songs, including "I Will Always Love You," one of the best-selling singles of all time) and a shrewd awareness of how to market her cheerful persona and simple-country-girl backstory.
She does primarily via Dollywood, a theme park she bought and rebranded in 1986, and which draws millions to its gates each year.
7. Jay-Z: $475 million
So what if he doesn’t have the biggest stake in the Brooklyn Nets.
The record-setting solo artist (12 #1 albums!) and erstwhile CEO of Def Jam co-created his Roc Nation entertainment conglomerate with Live Nation in 2008; co-authored Decoded, a bombastic tribute to globetrotting excess in 2011; and co-created the world’s luckiest baby the next year.
6. Mariah Carey: $500 million
Carey’s been banking off that five-octave range since Nicki Minaj was actually playing with Barbies.
Her stats are the stuff of legend: an all-time record 18 #1 singles as a solo artist, more than 200 million albums sold worldwide, five Grammys, and the status as the most wealthy living female musician.
And then, of course, there’s "Idol."
5. Sean “Diddy” Combs: $550 million
Partly known for shepherding the Notorious B.I.G. through his tragically short career, Combs played a key role ushering in hip-hop’s late-1990s “jiggy” era via Bad Boy Entertainment.
With Sean John, he developed a clothing line with appeal beyond rap, to the tune of more than $100 million in annual profits.
Combs made his name in the music biz, but it produces only 20 percent of his revenue at this point. Most recently, he has focused on Ciroc Vodka and his own cable music network.
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4. Bing Crosby: $550 million
The man who sang “I Haven’t Had Time to Be a Millionaire” was incredibly wealthy.
Crosby ranked among the 10 richest Americans in the 1930s—before he sang “White Christmas” and became one of the biggest movie stars of the ‘40s.
His Bing Crosby Enterprises was the first pop artist entertainment empire, with properties ranging from television stations to Ampex magnetic tape technology to horse tracks.
3. Bono: $600 million
Paul Hewson is known as much for his global diplomacy and forays into venture capital as U2’s music.
His investment in Facebook’s IPO—via his Elevation Partners private equity firm—didn’t make him a billionaire, but U2’s “360 Tour” grossed nearly $800 million between 2009 and 2011, making it the biggest tour ever.
Combine that with Bono’s many investments (including a clothing line and a five-star hotel), the fact that the band owns all the rights to its own music, and the numbers add up quickly.
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2. Paul McCartney: $800 million
Guinness lists McCartney as the most successful composer and recording artist of all time. In addition to royalties from the Beatles back catalog, which tops the charts with each reissue, he’s reported to own more than 25,000 other copyrights, and his post-Beatles musical career has been huge, with Wings selling 8 million-plus albums in the U.S. alone.
His late wife Linda, herself part of the Eastman fortune, left him an inheritance of £200 million, and his recent tour grossed $87 million.
1. Andrew Lloyd Webber: $1.2 billion
Webber became the richest musician in history practicing one of its oldest forms: musical theater. His ubiquitous works, which include "Jesus Christ Superstar," "Cats," and "The Phantom of the Opera," continue to bring in bundles with theatrical stagings, soundtrack recordings, and film adaptations.
On top of all this, Webber’s Really Useful Group profits diversified with ticketing agencies and venues.
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