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How Brad Pitt bounced back to regain his crown as Hollywood’s golden boy

The Hollywood superstar and two-time Oscar winner is proving that his acting skills are matched only by his mastery for reinvention, a keen business brain and a Midas touch for success.

Brad Pitt

As the charismatic anarchist Tyler Durden in subversive street brawling movie Fight Club, Brad Pitt delivers the line, “Only after disaster can we be resurrected. It’s only after you’ve lost everything that you’re free to do anything.”

It’s a quote the 56-year-old might well reflect on as he polishes his latest Oscar while sipping a (these days, soft) drink and watching his bank balance edge over the US$300 million mark.

There’s no doubt that the past few years have been some of Brad’s rockiest yet. In fact, just four years ago, his personal life and career appeared to be in freefall after his marriage to fellow actor and activist Angelina Jolie collapsed in a media frenzy. Allegations of alcohol and marijuana abuse led to an ugly custody battle while unsubstantiated rumours of infidelity and even an FBI child abuse investigation after an incident with his eldest son, Maddox, then 15, on an airplane hit the headlines and TV news around the world.

No charges were brought, but Pitt’s reputation was in tatters. His fans had just about forgiven him for dumping first wife Jennifer Aniston for Jolie, but exoneration would be a tougher sell this time around. As Pitt himself puts it, certain things in his life had become “a problem”.

Brad Pitt (right) at a 2007 press conference in New Orleans, Louisiana revealing Pitt’s plans to spend US$12 million with his ‘Make It Right Project’ for ecologically sustainable homes to be built in the aftermath of Hurricane Katrina

“I can’t remember a day since I got out of college when I wasn’t boozing or had a spliff, or something,” he said at the time. “I mean, I stopped everything except boozing when I started my family. But even this last year, you know—things I wasn’t dealing with. I was boozing too much.”

“We may have been created equal, but we’re not born equal. It’s a lot to do with luck and you have to pass that on.”

Fast forward to January 2020 and there stood Pitt on the stage of LA’s Dolby Theatre grasping the Academy Award for Best Supporting Actor in Once Upon a Time in… Hollywood (his first Oscar in 2014 was as producer for 12 Years a Slave). He was laconic, charming, heartfelt and funny, his reincarnation to acting royalty complete as he reminded the audience that there’s a lot more to him than salacious gossip and a pretty face.

Having deliberately taken time away from the limelight to focus on his children, his health, and his skills behind the camera, winning that second Oscar means Pitt has once more emerged victorious. Not bad for a boy from Missouri.

And while everyone remembers the first rule of Fight Club, maybe the second is to pick yourself up, no matter how hard you’ve been punched in the gut.

ONE: The Campaign to Make Poverty History. U2’s Bono, Brad Pitt and actor Djimon Hounsou

For those in the know, Pitt is renowned as not only one of the most astute businessmen in the notoriously cutthroat film industry, with an unrivalled instinct for box office success as well as critical acclaim, but also as a globe-trotting philanthropist who has championed environmental causes for the entirety of his career.

Not that Pitt’s one to shout about his altruistic ventures saying, “In Missouri, we don’t talk about what we do – we just do it. If we talk about it, it’s seen as bragging.”

And “just doing it” is exactly how Pitt has always played it.

He supported the ONE Campaign to fight poverty and AIDS in sub-Saharan Africa and, with George Clooney and Matt Damon, founded Not On Our Watch, aimed at preventing ‘mass atrocities’. It wasn’t only his star power, it was his drive and dogged refusal to give up that impressed world leaders, major fundraisers and relief organisations.

After the devastation of Hurricane Katrina in 2005, he created the Make It Right Foundation, writing a personal cheque for US$5 million to help bankroll the construction of sustainable and affordable housing in New Orleans, and enable architects and builders to work together.

Then there is the Jolie Pitt Foundation, which he established jointly with his now ex-wife in 2006, with the aim of assisting “humanitarian causes around the world”. The couple themselves contributed US$8.5 million in the first year, and the foundation has since donated millions to Doctors Without Borders, UN refugee agencies and Global Action for Children.

In honour of the son and daughter the duo adopted from Cambodia and Ethiopia, Pitt also founded health centres in his children’s homelands to treat youngsters with Aids and tuberculosis.

Brad Pitt with his children (from left) Pax Jolie-Pitt, Shiloh Jolie-Pitt, and Maddox Jolie-Pitt at the premiere of Unbroken in Hollywood

And when the genetically blessed power couple welcomed their biological twins Knox Leon and Vivienne Marcheline and in 2008, the US$14 million fee they negotiated from Hello and People magazines went not into the parents’ pockets but straight to one of their charities.

“The latitude and longitudinal lines of where you are born determine your opportunity in life, and it’s not equal,” Pitt says. “We may have been created equal, but we’re not born equal. It’s a lot to do with luck and you have to pass that on.”

On the business front, Brad’s shrewd business acumen has always impressed seasoned studio bosses, even more so when he bought out Aniston from their movie production partnership Plan B Entertainment after they split in 2005 and guided the company to dizzying success.

Having already hit the ground running with blockbusters including Troy and Charlie and the Chocolate Factory, in 2006 The Departed became the first of the company’s three best picture winners (alongside 12 Years a Slave there was also 2016’s Moonlight).

A bottle of Miraval Rose 2012 from Angelina Jolie and Brad Pitt’s French vineyard on display at a German trade fair in 2013

More hits followed, including World War Z (budget: US$150 million, box office gross: US$531 million), Eat Pray Love (budget: US$60 million, box office gross: US$206 million) and The Big Short (budget: US$28 million, box office gross: US$133 million).

But Pitt doesn’t seem particularly bowled over by these wins, declaring emphatically, “Success is a beast. And it actually puts the emphasis on the wrong thing. You get away with more instead of looking within.”

Nevertheless, nine years ago, former wine buff Pitt spread his business empire further with the purchase of a 250-acre French vineyard for US$31 million. He’s spent the ensuing years improving the wine and revitalising the business. “By nature, I keep moving, man,” he explains. “My theory is, be the shark.”

“Our successes are one thing, but our failures are every bit as important.”

So successful was Pitt as a vintner that last year, a magnum of the vineyard’s Muse de Miraval sold for €2,600 at a charity auction, smashing the record for pink blush and prompting respected French newspaper Le Figaro to dub it “the superstar of rosé”.

That Pitt has got himself back on track is testament to both an enviable work ethic, and business decisions made as much with his head as his heart.

For the man who says, “Our successes are one thing, but our failures are every bit as important”, the breakneck speed of the rollercoaster of reinvention and resurrection has come to the end of its ride. How much sweeter that Oscar victory must have been.

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