Pitt had just seven minutes of screen time in the Geena Davis and Susan Sarandon cult classic "Thelma and Louise." The 1991 movie gave Pitt his first big break, albeit with a rather small payday of just $6,000, according to The Telegraph.
In 1995, Pitt earned $4 million for "Se7en" and in 1996, he earned $10 million for "Sleepers," according to Refinery29. By the late 1990s, Pitt's baseline paycheck was in the neighborhood of $17.5 million.
Today, Pitt's movie appearances still yield multimillion-dollar paydays.
His role as a 1960s stuntman in Tarantino's movie earned him his first Oscar win for acting, but his upfront payday for the film was significantly lower than the typical $20 million Pitt pulls in from other blockbusters like "World War Z." This can be attributed to differences in payment models.
The payment model varies for actors from movie to movie, and Pitt certainly isn't struggling because of it.
But that number isn't just from his paychecks as an actor — Pitt is also a producer.
He produced and acted in the 2015 Oscar-winning film "The Big Short," which grossed over $133.3 million worldwide.
That same year, he also produced and acted in "War Machine," which Netflix reportedly paid $60 million to acquire.
Pitt is currently the sole owner of Plan B, as he bought out Aniston's stake upon their divorce in 2005.
The production company's first movie was "Charlie and the Chocolate Factory," which ultimately grossed half a billion dollars worldwide. The company was also behind 2006's "The Departed," 2010's "Eat, Pray, Love," and 2011's "Moneyball."
More recently, Pitt and Plan B would go on to produce a number of culturally significant films, including "12 Years a Slave," "Selma," "Moonlight, "If Beale Street Could Talk," and "The Last Black Man in San Francisco."
While it is unclear how much money Pitt takes home as a producer, The Hollywood Reporter estimates that actors who cross over into producing successfully take home a decent chunk of change — for example, Adam Sandler earned $5 million to produce "Grown Ups 2," a movie he also starred in.
Pitt was paid $20 million to star in "Mr. & Mrs. Smith," where he met ex-wife Jolie.
The power couple went on to monetize their relationship in a number of ways. They sold never-before-seen photos of their growing family to media outlets — including some of the most expensive exclusive photos to date. After the birth of their twins, Knox and Vivienne, in 2008, Pitt and Jolie sold photo rights of the children to People and Hello! magazine for $14 million. They then reportedly donated those earnings to charity.
Both were involved in multiple philanthropic projects, even creating a joint foundation in 2006. Through the Jolie-Pitt Foundation, the pair made donations including $1 million toward humanitarian efforts in Darfur in 2007 and $2 million toward wildlife protection in Namibia in 2011.
In 2016, when the pair announced their split, Forbes estimated they had earned a combined $555 million since 2004. The divorce proceedings for their two-year marriage have been tricky, with parts of their real-estate portfolio still yet to be divvied up.
Jolie and Pitt have had a messy custody battle on top of difficulty separating assets: They are still arguing over who gets to keep the French estate, albeit privately with a judge.
Chateau Miraval, a 1,200-acre estate in Correns, France, has been part of the Jolie-Pitt real-estate portfolio since 2012, but they've reportedly rented the property since 2008. They bought the property for $67 million, according to Us Weekly.
It features 35 rooms and other non-residential spots like the chapel the pair were married in and a recording studio that Pink Floyd and Sting have used. The property also includes a vineyard that specifically produces rosé.
Pitt and Jolie brought in the Perrins, a French winemaking family known for their experience in Châteauneuf-du-Pape, to produce the wine. It is a 50-50 partnership, according to The Telegraph.
This business venture also undoubtedly earns Pitt a decent chunk of change. In June 2019, a single magnum bottle of Miraval sold for nearly $3,000 at a charity auction, according to Forbes. The rosé is now widely sold and was even featured at the "Once Upon a Time in Hollywood" premiere after party.
In addition to the French chateau, the Pitt-Jolie family enjoyed several other homes around the world.
Their homebase was presumably the compound in Los Feliz, California, that Pitt bought for $1.7 million in 1994. He reportedly spent years buying up adjacent property for added privacy in the Los Angeles neighborhood.
The pair bought a mansion in New Orleans' historic French Quarter for $3.5 million. They were neighbors with Matthew McConaughey for a while, until they listed the home for $6.5 million in 2015.
In 2007, they also purchased an apartment in Manhattan's Waldorf-Astoria, known for its prime location and heavy security.
The couple also reportedly purchased a home in Mallorca, Spain, for $2.65 million in June 2016. The eight-bedroom home has views of the Balearic Sea.
Pitt has also held other properties, including a Beverly Hills mansion he once shared with ex-wife Aniston that is currently on the market for $44.5 million and a bachelor pad in Malibu.
Through the Jolie-Pitt Foundation, Pitt has donated millions of dollars to various causes, personally donating part of his movie deal earnings to the foundation on a yearly basis. According to the Daily Mail, the foundation was worth $41 million in March 2019.
In addition to the Jolie-Pitt Foundation, Pitt has also been involved in other philanthropic endeavors indvidually.
He founded the Make It Right foundation in 2007 to rebuild homes in New Orleans following Hurricane Katrina. Through the foundation, Pitt put $26 million toward building 109 homes. The project was not without its pitfalls — rotting and collapsing new homes led to a lawsuit. Pitt made a statement through a spokesperson to NBC about the debacle in 2018: "I made a promise to the folks of the Lower Ninth to help them rebuild — it is a promise I intend to keep." In the most recent development, Pitt and other foundation directors asked the court to remove them from the lawsuit, but the request was denied by a judge in New Orleans in October 2019.
He also cofounded a humanitarian assistance organization called Not On Our Watch with "Ocean's Eleven" castmates George Clooney, Matt Damon, and Don Cheadle. The fund merged with an anti-war crime organization called The Sentry in 2019.
Those include spending family time aboard a superyacht that costs $100,000 per week to rent and riding limited edition Ducati motorcycles.
He has also teamed up with upscale brands like Breitling and Brioni, which outfit him in €7,000 ($9,000) wristwatches and tailored Italian suits that cost upwards of $6,000 in exchange for his services as a brand spokesperson.
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