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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.
Most recently, Pitt was paid $10 million for his role in Quentin Tarantino's "Once Upon a Time in Hollywood."
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.
For movies like "Ocean's Eleven" and "Inglorious Bastards," Pitt was paid a base salary, but he also received bonuses depending on the success of the film post-release.
Pitt founded a production company, Plan B Entertainment, with ex-wife Jennifer Aniston in 2001.
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."
Pitt's high-profile relationship with Angelina Jolie also earned the couple millions.
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.
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.
One of the couple's disputed assets is their sprawling French vineyard. The two were married on the estate in 2014.
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 still co-own the rosé brand made on the estate's property.
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.
As far as other real estate goes, Pitt and Jolie shared several properties.
In addition to the French chateau, the Pitt-Jolie family enjoyed several other homes around the world.
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.
Occasionally, Pitt will indulge in other millionaire activities.