_{BY LISETTE VOYTKO. EDITED BY ROB LAFRANCO.
ADDITIONAL REPORTING BY STEVEN BERTONI.}

There has never been a better time to be a sellout–especially if you’re a superstar holding the rights to decades of hits. Almost half of the top 25 earners, including Lord of the Rings director Peter Jackson and rocker Bruce Springsteen, secured their spots in the ranks by unloading all or pieces of their studios or music catalogs.

In December, Bruce Springsteen sold the masters and publishing rights to all his recorded music and songwriting—including 11 multi-platinum albums and five gold singles—for what sources say was almost $500 million. The buyer was Sony Music, parent company of his longtime label, Columbia Records. The blockbuster deal lands the 20-time Grammy winner at No. 2 on the Forbes list of Highest-Paid Entertainers of 2021, behind Lord of the Rings director Peter Jackson, who collected $600 million in cash after selling part of his visual-effects company for $1.6 billion in November. That deal made Jackson a billionaire.

The Boss isn’t the only rocker on a financial roll. Other classic acts to sell their lucrative music catalogs in the past year include Bob Dylan, Paul Simon and Neil Young, who hauled in a combined $500 million before fees, enough for each to earn a spot in this year’s rankings. “These deals haven’t been hand-to-hand combat,” says Jon Landau, Springsteen’s manager of nearly half a century. “Everybody is getting what is in their interest.”

Music libraries aren’t the only pieces of content selling for far more than a song. In the past two years, major streaming services have spent some $3.7 billion to secure the rights to TV hits such as Friends and Law & Order, helping land the creators of both shows on this year’s entertainers list. A world crazy for content nabbed South Park creators Matt Stone and Trey Parker a spot on this year’s list and a $900 million deal with Viacom, who wanted the 25-year-old hit for its streaming service. The top earning woman in entertainment last year, No. 12 Reese Witherspoon, makes the cut after selling a piece of her production company Hello Sunshine to private equity firm Blackstone at a $900 million valuation in August.

Jay-Z, Dwayne “The Rock” Johnson and Kanye West all grabbed spots among the top five with their own 9-figure sums, most of it earned not from rapping, producing or acting, but from selling champagne, tequila and sneakers. Even the comparatively fresh-faced Taylor Swift, No. 25 with $52 million, made most of her money re-recording albums she first released a decade ago.

Altogether the 25 Highest-Paid Entertainers earned a combined $4.4 billion before taxes and fees in 2021, the vast majority of whom did it without creating anything new. (This is double the $2.2 billion that the top 25 celebrities earned in 2020.) Says Tom Freston, the former Viacom executive who greenlit South Park back when VHS tapes were still circulating: “There is so much choice these days. People gravitate to what they know.”

| 1 | Peter Jackson • $580 million

The Lord of the Rings director sold part of his visual effects firm Weta Digital to Unity Software for $1.6 billion in November, making him only the third person in history to become a billionaire (after Steven Spielberg and George Lucas) by making movies.

| 2 | Bruce Springsteen • $435 million

The Boss unloaded his entire body of work to his longtime label home Sony Music Group in December. The sale, estimated at nearly $500 million, included five decades of iconic songs, recordings and songwriting credits from 20 studio albums, multiple box sets and live recordings.

| 3 | Jay-Z • $340 million

Hip-hop’s first billionaire showed his business chops in 2021 when he cashed out stakes in music streamer Tidal and the Armand de Brignac champagne brand.

| 4 | Dwayne “The Rock” Johnson • $270 million

One of the few actors to make the ranking this year, The Rock got only about a quarter of his earnings from roles in films like Jungle Cruise and Red Notice, with most of his Jumanji-sized payday coming from his buzzy tequila brand Teremana.

| 5 | Kanye West • $235 million

The billionaire rapper-producer now earns most of his money from a multi-year deal to design Yeezy sneakers for Adidas. His first Yeezys designed for the Gap—a hoodie and jacket— arrived last year, quickly selling out. But the 52-year-old brand wants more and is reportedly frustrated by the slow rollout.

| 6 | Trey Parker and Matt Stone • $210 million

Shocking. Hilarious. And cheap to make. The creators of South Park–and its offshoots–oversee a cottage industry that now nets more than $80 million a year and, in August, they signed a six-year, $900 million deal with Paramount+.

| 7 | Paul Simon • $200 million

The folk rock musician sold hundreds of song compositions, including “Mrs. Robinson,” “59th Street Bridge Song (Feelin’ Groovy)” and “The Sound of Silence” to Sony Music Publishing for some $250 million in March.

| 8 | Tyler Perry • $165 million

The billionaire do-it-all creator and actor is bringing back the Madea franchise that made him famous – but everything he built around it is what brings in most of his earnings, from a multi-year production deal with BET to the 330-acre production studio he works out of in Atlanta.

| 9 | Ryan Tedder • $160 million

In addition to the 500-plus songs he has written for his own band, the OneRepublic frontman has penned hits for Beyoncé, Adele and Ed Sheeran. He sold a chunk of the catalog to investment firm KKR in January.

| 10 | Bob Dylan • $130 million

The 80-year-old Nobel laureate transferred his recorded music and a few future recordings to Sony in July for $150 million. That was on the heels of a reported $400 million megadeal in 2020 to sell his publishing catalog to Universal.

| 11 | Red Hot Chili Peppers • $116 million

London music investment fund Hipgnosis snapped up the California rockers’ catalog including such hit songs as “Californication” in May.

| 12 | Reese Witherspoon • $115 million

The Big Little Lies star sold her female-focused production company Hello Sunshine to private equity firm Blackstone at a $900 million valuation in August; she still has a stake. The actress also got a reported $20 million collected from 10 episodes of The Morning Show’s second season.

| 13 | Chuck Lorre • $100 million

The go-to guy at Warner Bros. TV is still collecting tens of millions a year from the syndication of such hits as Two And A Half Men and The Big Bang Theory, but he’s not been idle. The showrunner has four sitcoms currently airing as well as Netflix series The Kominsky Method.

| 14 | Sean “Diddy” Combs • $90 million

“I ain’t foolin’ around I’m building assets,” the young impresario told Forbes in 1999–and he wasn’t kidding. He still owns the brands he was building back then, including Bad Boy Records and the newly re-acquired Sean Jean fashion label, but most of his earnings these days comes from his Cîroc vodka liquor brand.

| 15 | Dick Wolf • $86 million

Dun-dun! Even after 32 years, Wolf’s Law & Order franchise continues to hook crime junkies with a combo of new shows (Organized Crime) and syndicated older ones (Special Victims Unit)–while making money on it all from a profit-share deal with Universal Television that most creators would kill for.

| 16 | Howard Stern • $85 million

The self-proclaimed “king of all media” moved from radio to SiriusXM satellite 15 years ago. In 2020, the one-time radio shock-jock re-upped with SiriusXM on a five-year, $500 million deal.

| 17 | Kevin Bright, Marta Kauffman, David Crane • $82 million

Friends forever: The show runners responsible for the quintessential 90s sitcom resurfaced for a moment when they brought back the cast for a reunion show on HBO Max. The trio continues to cash in with a deal on the streamer that locked up the laughs for $425 million.

| 18 | Shonda Rhimes • $81 million

The Bridgerton producer made a bet on herself when she signed with Netflix in 2017 and wowed executives there with one of the streamer’s most talked about pandemic releases. She re-upped with Netflix in July and continues to receive hefty residuals from ABC for Grey’s Anatomy.

| 19 | Neil Young • $80 million

In January, a year after he sold his music rights to investment fund Hipgnosis, Young told Spotify to pick between him and Joe Rogan, who allegedly spread Covid misinformation. The streaming service removed his music.

| 20 | Greg Berlanti • $75 million

The showrunner is known for his bevy of CW hits like Riverdale, but most of his income comes from a six-year production deal with Netflix for shows like the psychological thriller You.

| 21 | Lindsey Buckingham• $73 million

Fleetwood Mac’s renowned guitarist offloaded his publishing catalog to London’s Hipgnosis in January 2021, collecting on a lifetime of hits including “Go Your Own Way,” “The Chain” and “Tusk.

| 22 | Mötley Crüe • $72 million

The 1980s heavy metal band, known as much for their hedonism and crazy hair as perhaps their music, sold the rights to songs including “Kickstart My Heart,” “Dr. Feelgood” and “Girls, Girls, Girls” from their nine studio albums to music rights holder BMG.”

| 23 | Beach Boys • $64 million

The godfathers of surf rock sold a controlling interest in their intellectual property to legendary music executive Irving Azoff in February 2021.

| 24 | Blake Shelton • $55 million

The country star sold his music catalog in 2021 but another big payday was in television–where he gets paid a reported $13 million from his coaching gig on The Voice–and from $14.5 million made in a 15-city tour.

| 25 | Taylor Swift • $52 million

The 32-year-old songwriter turned anger into profit by remaking and releasing recordings sold by Scooter Braun without her consent in 2020; she also brought in earnings thanks to lucrative Peloton and Starbucks endorsement deals.

METHODOLOGY

Figures represent 2021 pretax earnings, minus fees for representation – managers, lawyers, agents – and/or business operating costs. Sources include data from Nielsen BookScan, MRC Data, Pollstar, IMDBPro and Variety Insight, as well as interviews with agents, lawyers, managers, executives and industry experts.