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The 25 Highest-Paid Athletes Of All Time

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The NBA is flush with cash right now thanks to its $24 billion TV deal with ESPN and TNT, as well as its global opportunities. Players are sharing in the riches, with 29 current NBAers in the middle of contracts worth at least $94 million in deals that range from three years in the case of LeBron James to five years for most of the 28 others, according to data from Spotrac. The significance of $94 million: It is more than the career earnings from playing salary of the sport’s greatest player, Michael Jordan, who earned $93.8 million with the Chicago Bulls and the Washington Wizards.

But don’t shed a tear for MJ. Sure, he made more than $4 million during only two of his 15 seasons in the NBA (Bulls owner Jerry Reinsdorf also paid Jordan his $4 million salary during the full season he took off to play baseball). Yet Jordan elevated athlete endorsements to an entirely new level, which has continued long after he hung up his high-tops for good in 2003. The result: Jordan is the highest-paid athlete of all time at $1.85 billion in 2017 dollars (the tally is $1.5 billion in current dollars).

Jordan has partnered with dozens of brands since he turned pro in 1984, including Gatorade, Hanes, MCI, Oakley, Upper Deck, Wheaties and more. His biggest backer has always been Nike, which signed Jordan ahead of his rookie year to a five-year deal worth $2.5 million, plus royalties. The Jordan Brand exploded for Nike and is now a $3.1 billion global business with revenue up 13% over last year and $800 million from two years ago. Jordan’s estimated cut of the business is $140 million this year.

Jordan showed the path to a fortune built on endorsement earnings that has since been followed by Tiger Woods, who ranks second at $1.7 billion. Like Jordan, Woods reached the pinnacle of his sport while shying away from any controversy, making him a marketing darling for sponsors like Accenture, American Express, EA Sports, General Motors and Nike.

READ MORE: Serena Williams Heads The Highest-Paid Female Athletes 2017

Woods banked $600 million (adjusted for inflation) between 2006 and 2010, with endorsements and appearance fees fueling most of the earnings. The image of Woods as the perfect pitchman came crashing down on a Thanksgiving night eight years ago, but he remains the top draw in golf when healthy. His earnings are off 68% from their peak but still rank among the highest in golf.

Forbes‘ earnings estimates include salaries, bonuses, prize money, endorsements and licensing, as well as fees from books, golf course designs and appearances. Earnings cover from the time the athletes turned pro through June 1, 2017, and include money earned after playing careers were over, as well as earnings by the estate in the case of Arnold Palmer. We do not include investment income, and we back-filled years where we did not publish earnings figures, such as prior to 1990 for Palmer and Jack Nicklaus. We adjusted all figures for inflation.

The 25 highest-paid athletes of all time played a mix of eight sports, with golf, basketball and boxing landing five entries each. The top 25 have earned a cumulative $19.4 billion since turning pro ($15.9 billion without adjusting for inflation).

READ MORE: Ronaldo, Le Bron Top World’s Highest-Paid Athletes Of 2017

From branding it like Beckham to the Golden Bear’s Midas touch, these sports legends are so money when it comes to career earnings and endorsement deals.

The Highest-Paid Athletes of All-Time

1. Michael Jordan

Career earnings: $1.85 billion (2017 dollars)

Jordan still maintains his longtime endorsement relationships with Gatorade, Hanes, Nike and Upper Deck, but the investment that made him a billionaire was the $175 million fire-sale price he got the Charlotte Bobcats (now the Hornets) for in 2010. Jordan bumped his Hornets stake to 90% in 2013, and the team is now worth $780 million.

2. Tiger Woods

Tiger Woods

Tiger Woods during the Hero World Challenge at Albany, Bahamas in Nassau, Bahamas. (Photo by Mike Ehrmann/Getty Images)

Career earnings: $1.7 billion

The 14-time major winner has played only 18 official PGA Tour events since the start of 2014 because of injuries (he’s missed the cut or withdrawn from half of them). Sponsors still see value in partnering with Woods, with TaylorMade, Bridgestone and Monster Energy the most recent additions to his endorsement portfolio.

3. Arnold Palmer

Career earnings: $1.4 billion

Palmer died in September 2016, but his estate still banked $40 million during the last 12 months. More than 400 stores sell Arnold Palmer-branded apparel in Asia, with plans to move into new markets like Thailand and Vietnam. His estate has agreements with 39 licensees. The partnership between IMG founder Mark McCormack and his first client, Palmer, revolutionized sports marketing.

4. Jack Nicklaus

Career earnings: $1.2 billion

Nicklaus’ course design company is responsible for 410 courses in 41 countries, with the 18-time major winner involved in three-quarters of the projects. In addition to course design, the Nicklaus business empire includes real estate, wine, ice cream, drinkware, golf academies, lemonade and more.

5. Michael Schumacher

Career earnings: $1 billion

The health of Schumacher, 47, has been precarious since a 2013 skiing accident in the Alps left him in a coma. The F1 titan dominated his sport while racking up seven titles and is one of only six athletes to top the FORBES highest-paid athletes list since 1990.

6. Phil Mickelson

Career earnings: $815 million

Mickelson pitches for Amgen, ExxonMobil, KPMG, Rolex, Grayhawk and the Greenbrier, as well as two new partners in Intrepid Financial Partners and Workday. His $84 million in career prize money ranks second all-time. Coming in second to Tiger has been plenty lucrative for Lefty, who finally outearned his rival in 2015, for the first time since Woods turned pro in 1996.

7. (tie) Kobe Bryant

Career earnings: $800 million

Bryant’s earnings during his playing career were tops all time among team athletes, and he had the highest NBA salary the final six seasons of his career. The Black Mamba is attacking retirement the way he did opposing guards during his 20-year NBA career. He launched Kobe Inc. and a venture capital firm, Bryant Stibel, with $100 million in funding.

7. (tie) David Beckham

Career earnings: $800 million

Beckham’s most lucrative years have come in retirement thanks to royalty deals with Diageo, to launch a new single-grain Scotch whisky called Haig Club, and Global Brands Group, to create Beckham-branded consumer products. Beckham is inching closer to bringing an MLS expansion team to Miami, which he got the rights to at the bargain-basement price of $25 million.

9. Floyd Mayweather

Floyd Mayweather Jr. v Conor McGregor

Dana White splits Floyd Mayweather Jr. and Conor McGregor apart during the World Press Tour at SSE Arena on July 14, 2017 in London, England. (Photo by Matthew Lewis/Getty Images)

Career earnings: $785 million

Our earnings figure for Mayweather does not include his monster payday for his August bout against Conor McGregor (our scoring period ended June 1). His McGregor paycheck makes Mayweather just the sixth athlete ever with earnings of $1 billion.

10. Shaquille O’Neal

Career earnings: $735 million

O’Neal sold a stake in the business of Shaq last year to Authentic Brands Group, which got the rights to roughly half of O’Neal’s future licensing and endorsement revenue in return for a lump sum payment. Shaq’s low-cost sneaker line has sold more than 120 million pairs during his career.

11. LeBron James

Career earnings: $730 million

The NBA’s top pitchman added Intel and Verizon this year to his endorsement portfolio, which already included Nike, Coca-Cola, Beats by Dre and Kia Motor. King James owns a stake in 17 Blaze Pizzas, the fastest-growing food-service business of all-time.

12. Cristiano Ronaldo

Cristiano Ronaldo

Cristiano Ronaldo of Real Madrid during the La Liga match against Sevilla at Santiago Bernabeu Stadium in Madrid, Spain. (Photo by Power Sport Images/Getty Images)

Career earnings: $725 million

Ronaldo is rising up the charts as the highest-paid athlete in the world the past two years, including $93 million in the 12 months ending in June. His Real Madrid contract extension will push the earnings for soccer’s reigning player of the year even higher.

13. Greg Norman

Career earnings: $705 million

Like Shaquille O’Neal and Muhammad Ali before him, Norman sold his future licensing rights to Authentic Brands Group in March. Norman’s company retains control of his real estate, investments and course design operations, but ABG will work on his other business interests in apparel, accessories, steak and wine.

14. Mike Tyson

Career earnings: $700 million

The youngest heavyweight champion in the history of boxing squandered $400 million in earnings (not adjusted for inflation) before filing for bankruptcy in 2003. Tyson has reinvented himself at 51 as an actor and with business partnerships around gaming, motorcycles and fitness centers.

15. Roger Federer

Roger Federer

Roger Federer of Switzerland celebrates after beating Marin Cilic of Croatia during the ATP World Tour Finals at The O2 Arena, London. (Photo by Kieran Galvin/NurPhoto via Getty Images)

Career earnings: $675 million

Federer recently re-took the crown for highest career prize money on the ATP Tour with his resurgent year on the court in 2017. His $111.9 million tally surpasses the total of Novak Djokovic ($109.8 million), as well as that of Tiger Woods, who sits at $110 million in prize money on the PGA Tour.

16. Lionel Messi

Career earnings: $600 million

Messi has been at Barcelona since age 13, and his contract extension last month will keep him at Camp Nou through the 2020-21 season. The buyout clause for Barcelona’s all-time leading scorer doubled under the new deal to $835 million.

17. Alex Rodriguez

Career earnings: $575 million

A-Rod signed two of the three biggest contracts in the history of baseball during his 22-year career and was paid $20 million by the Yankees in 2017 despite retiring last year. He has been busy in retirement as a Fox Sports analyst and a host for an upcoming CNBC reality show, in addition to his high-profile relationship with Jennifer Lopez.

18. Jeff Gordon

Career earnings: $525 million

Gordon won 93 races during his Nascar career, the modern-day record. He owns a stake in Jimmie Johnson’s No. 48 car and could be in line for a larger ownership role at Hendrick Motorsports.

19. Oscar De La Hoya

Career earnings: $520 million

The Golden Boy’s 2007 fight with Floyd Mayweather was the biggest bout in pay-per-view history, with 2.5 million buys, until Mayweather faced Manny Pacquiao. De La Hoya earned a then-record $52 million because he served as the fight’s promoter through his company Golden Boy Promotions, which he founded in 2002.

20. Manny Pacquiao

Career earnings: $510 million

Pacquiao’s pay-per-view career includes 18.6 million buys and gross revenue of $1.2 billion. The Filipino senator lost to Australian Jeff Horn in his only 2017 bout. Pacquiao’s biggest career payday was his 2015 fight with Mayweather, for which he pocketed roughly $125 million.

21. Derek Jeter

Career earnings: $490 million

Jeter’s tenure as an MLB owner is off to a rocky start in South Florida. The 14-time All-Star put up only $25 million of the $1.2 billion price for the Miami Marlins, but Jeter is calling the shots as CEO of the team.

22. (tie) Peyton Manning

Career earnings: $480 million

The five-time MVP retired as the NFL’s all-time leader in passing yards (71,490) and touchdowns (539) and was the NFL record-holder for earnings on and off the field. Manning remains a popular pitchman in retirement, shilling for Nationwide, DirecTV, Gatorade, Papa John’s and Otterbox. He also hosted the 2017 ESPYs.

22. (tie) Kevin Garnett

Career earnings: $480 million

Garnett earned an NBA-record $334 million in playing salary during his 22-year playing career with the Timberwolves, the Celtics and the Nets. His blockbuster six-year, $126 million contract as a 21-year-old in 1997 helped push NBA owners to lock out the players ahead of the 1998-99 season.

24. Evander Holyfield

Career earnings: $475 million

Holyfield’s career-high payday was $34 million, for his second fight versus Mike Tyson, which ended abruptly when Tyson was disqualified for biting off a chunk of Holyfield’s ear. Despite a quarter-century of boxing purses, Holyfield faced major financial issues with a foreclosure of his $10 million, 109-room Atlanta estate and lawsuits for unpaid child support.

25. Andre Agassi

Career earnings: $470 million

Agassi’s massive Nike endorsement deal earned him $140 million over 10 years, including the appreciation of the company stock he received in the pact.

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The Highest-Paid Tennis Players 2019: Roger Federer Scores A Record $93 Million

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Roger Federer, Novak Djokovic and Rafael Nadal are kicking off play at the U.S. Open as the three favorites to win the title and take home a Grand Slam-record $3.85 million payday as the singles champion. The Big Three are a good bet, having captured 53 out of 63 Slams since the start of 2004, including the last 11.

The on-court dominance has produced a combined $373 million in career prize money for the trio, light years ahead of their peers. But the money off the court is even sweeter for Federer, Djokovic and Nadal, to the tune of a cumulative $1.2 billion during their careers from endorsement partners and appearance fees.

Federer is the highest-paid tennis player for the 14th straight year, with $93.4 million from prize money, endorsements and appearance fees in the 12 months ending June 1. It is a record tally by a tennis player.

READ MORE | Inside Serena Williams’ Plan To Ace Venture Investing

His sponsor portfolio is unmatched in sports, with a dozen partners together paying him more than $60 million a year, well ahead of other global sports icons like Tiger Woods, LeBron James and Cristiano Ronaldo.

Credit Federer’s long run at the top—his Slam titles span 15 years—and the strong demographics of tennis fans, who spend heavily on equipment, apparel, cars, watches and financial services. The global nature of the sport also allows brands to use the players in marketing around the world.

Federer turned 38 this month, and Father Time will catch up at some point, but Japanese apparel brand Uniqlo is betting $300 million that Federer will continue to resonate with fans long after he hangs up his racket.

READ MORE | Business Is Booming For Tennis Ace Naomi Osaka, On Track To Be The Highest-Paid Female Athlete

After two decades with Nike, Federer signed a ten-year deal with Uniqlo last year that is guaranteed whether he is playing or not. In the coming months, Federer will also likely take back control of his RF logo, which stayed with Nike after their split.

After a two-year Slam drought, Djokovic has roared back to capture four of the past five majors. The titles helped push his 12-month earnings to $50.6 million, including $30 million off the court from appearances and sponsors Lacoste, Head, Asics, Seiko, NetJets and Ultimate Software. He ranks as the second-highest-paid tennis player.

Rounding out the top five players are Kei Nishikori ($37.3 million), Nadal ($35 million) and Serena Williams ($29.2 million).

Tennis is the only major sport in which women and men are in the same zip code in terms of earnings. The U.S. Open was the first Slam to offer equal payouts for the men’s and women’s events, and now each of the four Slams has equal pay. While Williams was the only woman to crack Forbes‘ 100 highest-paid athletes this year, the top ten earners in tennis are split evenly between men and women.

The top ten collectively made $312 million, up 23% from last year, fueled by huge gains by Federer, Djokovic and Naomi Osaka. See the full top ten below.

10. Sloane Stephens

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Total earnings: $9.6 million

Prize money: $4.1 million

Endorsements: $5.5 million

The 2017 U.S. Open champion returns to Flushing Meadows this year wearing a tennis shoe based on the “Aqua” colorway of Nike’s retro Air Jordan VIII. Her Nike pact, which began last year, is one of the biggest in the sport. Stephens recently announced her engagement to soccer star Jozy Altidore.

9. Simona Halep

The Championships - Wimbledon 2019
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Total earnings: $10.2 million

Prize money: $6.2 million

Endorsements: $4 million

Halep has won only one event in 2019, but it was a big one: Wimbledon, and its $3 million payday, her second career Grand Slam title. The Romanian pro counts Nike, Wilson, Mercedes-Benz and Hublot among her sponsors.

8. Angelique Kerber

Nature Valley International - Day Four
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Total earnings: $11.3 million

Prize money: $5.3 million

Endorsements: $6 million

Kerber triggered lucrative bonuses from sponsors, namely Adidas, with her 2018 Wimbledon title and year-end rank of second in the world. In addition to Adidas, the German pro has also renewed deals with SAP, Generali and NetJets since Wimbleon and recently inked a new pact with Procter & Gamble’s Head & Shoulders brand. Other endorsements include Yonex, Porsche, Rolex and Lavazza.

7. Alexander Zverev

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Total earnings: $11.8 million

Prize money: $6.3 million

Endorsements: $5.5 million

The 22-year-old German is a rising star on the ATP Tour and has 11 career titles, including the 2018 year-end ATP Finals, which was worth $2.5 million in prize money. He has a large deal with Adidas, in addition to endorsements with Head, Peugeot, Richard Mille and Zegna.

6. Naomi Osaka

Western & Southern Open - Day 5
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Total earnings: $24.3 million

Prize money: $8.3 million

Endorsements: $16 million

Osaka will see her endorsement number soar even higher, having signed a series of deals since her 2018 U.S. Open win. The biggest is with Nike, which was inked just ahead of our June 1 cutoff and is worth an estimated $10 million annually. She also recently added a series of endorsement partners—Hyperice, BodyArmor and Muzik—where she received equity stakes in the businesses.

5. Serena Williams

Rogers Cup Toronto - Day 6
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Total earnings: $29.2 million

Prize money: $4.2 million

Endorsements: $25 million

The world’s highest-paid female athlete four years running had a record year off the court after her return to tennis following the birth of daughter Olympia. She added deals with Pampers, Axa Financial and General Mills to her roster. Williams’ next act is tackling venture investing, focused largely on companies led by women or people of color.

4. Rafael Nadal

Rogers Cup Montreal - Day 10
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Total earnings: $35 million

Prize money: $9 million

Endorsements: $26 million

The Spaniard is one of the biggest draws in tennis and can command appearance fees of more than $1 million a pop. His primary sponsors include Nike, Babolat, Kia Motors, Telefónica, Richard Mille and Mapfre.

3. Kei Nishikori

TENNIS: AUG 07 Coupe Rogers
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Total earnings: $37.3 million

Prize money: $4.3 million

Endorsements: $33 million

Nishikori and Zverev are the only non-Slam winners among the ten highest-paid tennis players. But Nishikori’s robust endorsement portfolio is fueled by his status as the most successful Japanese player ever. He is set to be one of the faces of the 2020 Olympic Games in Tokyo. His sponsors Asahi, NTT, Japan Airlines, Lixil, Procter & Gamble and Nissin are all official Olympics partners.

2. Novak Djokovic

Western & Southern Open - Day 6
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Total earnings: $50.6 million

Prize money: $20.6 million

Endorsements: $30 million

There have been ten tennis seasons in which a player won more than $12 million in prize money. Djokovic owns seven of those years. His $135 million in career prize money has him $9 million ahead of Federer. Djokovic’s Lacoste endorsement is one of the richest deals in the sport.

1. Roger Federer

Day Eleven: The Championships - Wimbledon 2019
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Total earnings: $93.4 million

Prize money: $7.4 million

Endorsements: $86 million

In addition to his blockbuster Uniqlo pact, Federer added a multimillion-dollar deal with Rimowa last year. The luggage brand joined Credit Suisse, Mercedes-Benz, Rolex, Moet & Chandon, Barilla and others in Fed’s endorsement stable.

-Kurt Badenhausen; Forbes

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The Highest-Paid Actors 2019: Dwayne Johnson, Bradley Cooper And Chris Hemsworth

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A bankable leading man is still one of Hollywood’s surest bets, even if your name isn’t Leonardo DiCaprio. While the lucrative twenty-twenty deal ($20 million upfront and 20% of gross profit) doled out to the likes of Harrison Ford and Tom Cruise may be more or less gone, Hollywood still has its big-money brands, those actors who can promise an audience so big that they command not only an eight-figure salary to show up on set but also a decent chunk of a film’s nebulous “pool”—or the money left over after some but not all of the bills are paid. 

Dwayne Johnson, also known as the Rock, tops the Forbes list of the world’s ten highest-paid actors, collecting $89.4 million between June 1, 2018, and June 1, 2019.

READ MORE | Marvel Money: How Six Avengers Made $340 Million Last Year

“It has to be audience first. What does the audience want, and what is the best scenario that we can create that will send them home happy?” Johnson told Forbes in 2018.

It seems he makes the audience happy. Johnson has landed a pay formula as close to the famed twenty-twenty deal of yore as any star can get these days. He’ll collect an upfront salary of up to $23.5 million—his highest quote yet—for the forthcoming Jumanji: The Next Level.

He also commands up to 15% of the pool from high-grossing franchise movies, including Jumanji: Welcome to the Jungle, which had a worldwide box office of $962.1 million. And he is paid $700,000 per episode for HBO’s Ballers and seven figures in royalties for his line of clothing, shoes and headphones with Under Armour.

READ MORE | ‘Black Panther’: All The Box Office Records It Broke (And Almost Broke) In Its $235M Debut

While Johnson’s deal is the biggest in the business right now, he’s not the only one with a lucrative deal. Robert Downey Jr. gets $20 million upfront and nearly 8% of the pool for his role as Iron Man, and that amounted to about $55 million for his work in Avengers: Endgame, which grossed $2.796 billion at the box office. 

That gross was so big that it secured spots on this year’s top-earner list for Chris Hemsworth, Bradley Cooper and Paul Rudd, in addition to Downey; together, they earned $284 million, with most of that coming from the franchise. 

“Celebrities such as Downey and (Scarlett) Johansson currently have extreme leverage to demand enormous compensation packages from studios investing hundreds of millions of dollars in making tent-pole films, such as The Avengers series,” entertainment lawyer David Chidekel of Early Sullivan Wright Gizer & McRae told Forbes. 

READ MORE | Worldwide Box Office, The Best It’s Ever Been

Cooper is the rare actor who can thank a bet on himself for his 2019 ranking. The actor earned only about 10% of his $57 million payday for voicing Rocket Raccoon in Avengers. 

Seventy percent came from A Star Is Born, the smaller musical drama that he directed, produced, cowrote and starred in with Lady Gaga. The movie was a passion project for Cooper, and he forfeited any upfront salary to go into the film and Gaga’s salary. It paid off—the movie, which had a production budget of only $36 million, grossed $435 million worldwide, leaving Cooper with an estimated $40 million. 

The full list is below. Earnings estimates are based on data from Nielsen, ComScore, Box Office Mojo and IMDB, as well as interviews with industry insiders. All figures are pretax; fees for agents, managers and lawyers (generally 10%, 15% and 5%, respectively) are not deducted.

The World’s Highest-Paid Actors Of 2019

10. Will Smith

Earnings: $35 million

9. Paul Rudd

Earnings: $41 million

8. Chris Evans

Earnings: $43.5 million

6. Adam Sandler (tie)

Earnings: $57 million

6. Bradley Cooper (tie)

Earnings: $57 million

5. Jackie Chan

Earnings: $58 million

4. Akshay Kumar

Earnings: $65 million

3. Robert Downey Jr.

Earnings: $66 million

2. Chris Hemsworth

Earnings: $76.4 million

1. Dwayne Johnson

-Madeline Berg; Forbes

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Comedian Jim Gaffigan Rakes In $30 Million By Ditching Netflix And Betting On Himself

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Gripping a lukewarm Heineken, Jim Gaffigan hunches his six-foot-one frame over a peeling table in the green room of the An Grianán Theatre in Letterkenny, Ireland. Summer nights are never terribly hot in these parts, but this one is warm enough to need some air conditioning, which the theater almost never uses. It’s hardly a glamorous moment. But then again, glamour isn’t really his thing.

“There’s nothing sexy about Jim Gaffigan,” he says, sweat dotting his brow. “I’m not young. I don’t have a full head of hair. I’m out of shape. I don’t talk about having dinner with Kanye.”

Fortunately for him, he is funny. Just ask the more than 300,000 people in 15 countries who’ve paid an average of $56 to see his latest routine. For the 53-year-old father of five, it’s been a grueling schedule: more than 75 cities in the past year, including whistle-stops like Letterkenny, a northern community of 20,000 that was once lauded as the Republic’s “tidiest town.”

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They may not offer much sizzle, but places like this are the lifeblood of Gaffigan’s business. He has raked in $30 million this year, putting him at No. 3 on Forbes’ list of the highest-earning stand-up comedians. Half of that was earned by putting “butts in seats.”

The rest comes from spreading his punch lines far and wide. And in this business, if those jokes are funny enough—and your reach wide enough—you can fill a lot of seats with a lot of butts. With the right distribution deal, those jokes can deliver exponential returns. But that’s where it gets a bit tricky.

“In the entertainment industry, every house is made of ice and it’s melting,” Gaffigan says. “So you’d better be building a new house.”  

Gaffigan’s been building. In 2016, he agreed to partner with Netflix, the industry’s dominant force and home to original specials from all but one of the comedians on Forbes’ ranking. Last year he cut loose from the kingmaker and placed a bigger bet on himself, pairing up with Comedy Dynamics, an independent producer, to release his next special everywhere but Netflix. 

Gaffigan will star in the first original stand-up special on Amazon, which is going after the streaming giant with a push into comedy. Quality Time goes live today, and it can be shopped on the open streaming market when its exclusive run with Amazon Prime Video is up in two years. And that market is only expanding.

Gaffigan has learned a bit about home building in the entertainment industry. He cut his teeth on the club circuit in the early 1990s, when HBO was the primary destination for stand-up specials and Comedy Central was a fledgling cable network.

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In 2000, he landed what was then the holy grail of comedy success—a broadcast sitcom—which was the source of the fortunes the creators of Seinfeld and Roseanne minted once they had enough seasons on the air and could sell the series into syndication.

Gaffigan’s shot proved to be short-lived, but six years later he scored a second chance and headlined a Comedy Central special called Beyond the Pale. This time it paid dividends, landing him his first theater show a month later. The butts were now coming to the seats, and while his rise was live, in person, with microphone in hand, his breakout was digital.

At the time, YouTube was changing the rules of the game, providing comedians a global platform with unprecedented distribution. Then Twitter emerged, giving comedy bookers a real-time assessment of who was attracting audiences.

READ MORE | The World’s Highest-Paid Comedians Of 2018

Then came the debut of streaming on Netflix, which latched onto comedy as a cheap and effective way to lure subscribers, while some, notably the now disgraced Louis C.K., used streaming to control their own distribution, making their shows available for fans to purchase directly.

“It was a technological wave that crashed over the stand-up world,” says Wayne Federman, a comedian and professor of the history of stand-up at the University of Southern California. “And we’re still all trying to figure out what’s going on.”

Gaffigan’s first original Netflix special aired in 2017, long after the company had reshaped the industry. It was a promising place to be: Aziz Ansari and Ali Wong were propelled into superstar status through their Netflix specials, while household names like Dave Chappelle and Jerry Seinfeld reportedly cashed in with $60 million (Chappelle) and $100 million (Seinfeld) paydays in exchange for long-term, multi-program deals. Gaffigan’s first special, Cinco, sold for a more modest seven-figure sum.

Jim Gaffigan stand up comedy specials for Netflix and Amazon Original
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It was more than just a check; it was access to a potential audience of nearly 94 million. Although Netflix’s subscriber base has grown since then, so has its stand-up library. The platform now shops nearly four times the number of original stand-up specials than when Cinco debuted.

That makes it harder to stand out in the scroll. Plus, the streamer often holds onto specials in perpetuity, including Cinco. The up-front money is nice, but there is no ability to earn on the back end. 

Gaffigan used his next special, 2018’s Noble Ape, which was directed and cowritten by his wife, Jeannie Gaffigan, to test the waters. Comedy Dynamics bought the rights and made it available everywhere Netflix wasn’t. It had a theatrical release and could be purchased and rented on multiple services, including  iTunes, YouTube and Walmart’s VUDU.

Later, there were short streaming windows on Comedy Central and Amazon Prime. According to Comedy Dynamics CEO Brian Volk-Weiss, it was even syndicated to planes and cruise ships. The up-front payment to Gaffigan from Comedy Dynamics was lower than at Netflix, but the wide distribution allowed him to earn on the back end, bringing in a total of $10 million, according to Forbes estimates.

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And new services are on the way from Apple, WarnerMedia, NBCUniversal and Disney, any one of which could choose to pursue cheap-to-produce and popular stand-up specials. 

Because of this widening field, stand-up specials may have more life (and revenue) in them, and that could be good for comedians looking to gamble on their success with deals that offer back-end participation. “We have titles in our library that are making more in year 12 than they made in year one,” says Volk-Weiss, whose company also owns specials by Bob Saget, Iliza Shlesinger and Janeane Garofalo.

Still, leaving Netflix means walking away from a partner that has now established itself as a formidable entertainment company. Netflix has some 180 original hour-long stand-up specials and is singularly focused on exploiting content around the world. Gaffigan, though, is content to keep the bet on himself.

“In the entertainment industry, every house is made of ice and it’s melting. So you’d better be building a new house.”

In the stuffy backstage room in Letterkenny, Gaffigan reviews some of the new material he tried out on stage. A joke about Ireland’s nonsensical roads killed it. He stumbled with a bit about the English. The classics played well—“My dad never went to a parent-teacher conference; my dad didn’t know I went to school.”  

And he’s well aware that Amazon’s core mission is to sell stuff, even though it has won critical acclaim for shows like The Marvelous Mrs. Maisel and Transparent. With plans to deliver three more specials over the next five years, he’s got time to see just how good a partner the retailer might be. Along the way, he may decide it’s time to find a new neighborhood.

“The reason I went to Amazon is to expand my audience,” he says. “I don’t know what they’re gonna do and I don’t fully understand their marketing might. I might be pleasantly surprised. I mean, it’s a huge corporation. They could probably make more selling socks.”

-Ariel Shapiro; Forbes

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