You can easily guess the wealthiest living musicians, but how do they stack up to the richest musicians ever? It helps to emerge at the right time (the late 1960s and early ‘70s or the mid- to late-‘90s, the two moments when the now-shrunken industry was at its largest), make shrewd investments (in publishing and elsewhere, but also by capitalizing on one’s own brand), and working across different media platforms (television, film, and touring). Adjusting fortunes going as far back the the pre-rock-and-roll era for inflation, we made some surprising discoveries.
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. (It helps that live theater has proven resistant to recent economic challenges.) On top of all this, Webber’s Really Useful Group, which he wisely set up in 1977, profits from his works in any form, incorporating ticketing agencies and venues.
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, and “Mull of Kintyre” becoming the first song to sell 2 million copies in the UK. His late wife Linda, herself part of the Eastman fortune, left him an inheritance of £200 million, and his recent tour “Up and Coming” grossed $87 million.
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. (2005-06’s “Vertigo” tour is fifth on that list.) Combine that with Bono’s many investments (including private equity stakes, a clothing line, and a five-star hotel), the fact that the band owns all the rights to its own music, and Bono’s Romney-esque tax-dodging investment schemes, and the numbers add up quickly.
4. Bing Crosby: $550 million
The man who sang “I Haven’t 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.
5. Sean “Diddy” Combs: $550 million
Sean Combs was first out of the gate in rap’s nascent empire-building moment of the early 1990s, 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. The music biz accounts for only 20% of his revenue at this point, with his attention most recently focused on Ciroc Vodka and his own cable music network.
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.
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-founded 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.
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.
9. Jimmy Buffett: $400 million
Buffett has been drawing his faithful Parrotheads and their battery-powered margarita blenders to ampitheaters every summer since 1976 via lucrative tours with titles like “Last Mango in Paris,” “Beach House on the Moon,” and “Summerzcool.” (2011’s tour raked in $22 million). 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. If you need a satirical primer for these khaki-clad weekend pilgrims, check out 30 Rock’s “Crabcatchers” episode.
10. Michael Jackson: $350 million
At its peak, his empire was vast—he was earning $50 million a year through the 1980s and 1990s. In 1985, with one of the biggest-selling albums ever (Thriller sales have been inflated, but the 66 million copies were sold worldwide), a series of incredibly lucrative tours, and a record $5 million deal with Pepsi (worth $11 million today), the questionable investments started coming quickly. He dropped $47.5 million to buy ATV Music ($101 million today), 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 (a total of $111 million today). By 2003, he held $200 million in debt, and even that wasn’t enough to break him.