Why Did Brad Pitt Do Two Harvey Weinstein Movies After Gwyneth Paltrow and Angelina Jolie Were Attacked?

The A-List actor and producer knew that Weinstein was a predator, yet still made ‘Inglourious Basterds’ (2009) and ‘Killing Them Softly’ (2012) with the mogul.

Photo Illustration by Elizabeth Brockway/The Daily Beast

In the wake of Tuesday’s shocking New Yorker exposé, several more actresses came forward with harrowing stories of sexual harassment and coercion at the hands of movie mogul Harvey Weinstein.

One of these brave women was Angelina Jolie, who said the lecherous studio executive had made unwanted advances to her in a hotel room around the release of 1998’s Playing by Heart, which was distributed by Weinstein-owned Miramax Films. “I had a bad experience with Harvey Weinstein in my youth, and as a result, chose never to work with him again and warn others when they did,” she told The New York Times. Another was Gwyneth Paltrow, who alleged that, prior to shooting what would prove to be her breakthrough role in 1996’s Emma, Weinstein approached the then-22-year-old actress in a Beverly Hills hotel suite, put his hands on her shoulders, and intimated that they move to the bedroom for “massages.” She immediately left, disgusted. “I was a kid, I was signed up, I was petrified,” she recalled to the Times.

The testimonies of Jolie and Paltrow proved particularly disturbing because they proved that Weinstein had the power and influence to silence anyone—even Hollywood royalty. Jolie, after all, is the daughter of Oscar-winning actor Jon Voight, and Paltrow the progeny of director Bruce Paltrow and actress Blythe Danner, and the goddaughter of Steven Spielberg.

Another thing these two talented women have in common is their proximity to the actor Brad Pitt. Paltrow dated Pitt from 1994-1997 before breaking off their engagement, while Jolie was Pitt’s partner from 2005-2016. Their divorce is still pending. In the Times piece, Paltrow said that she’d confided in Pitt about the Weinstein episode, and that the actor proceeded to confront Weinstein at a film premiere and warn him to never do anything like that to his girlfriend again. (Pitt confirmed as much to the Times.)

“Brad threatened Harvey. He got right in his face, poked him in the chest, and said, ‘You will not ever do this to Gwyneth ever again,’” a source told People, adding that if Weinstein did try anything again, the Springfield native told the portly New Yorker he’d get a good “Missouri whooping.”

Many online were quick to praise Pitt, then a rising star, for giving a studio bigwig like Weinstein the business—something that precious few Hollywood men felt compelled to do both during the mogul’s three-decade reign of terror and after the sickening revelations came to light. But why, then, did Pitt continue to work with Weinstein not once, but twice: on 2009’s Inglourious Basterds and 2012’s Killing Them Softly?

The Weinstein allegations have led to a broader discussion of Hollywood complicity—the power brokers who were not only aware of his despicable behavior but may have helped facilitate his hotel liaisons with a bevy of up-and-coming actresses. Paltrow told the Times that her hotel “meeting” with Weinstein was listed “on a schedule from her agents,” while the actress Rose McGowan, who reportedly agreed to a $100,000 settlement with Weinstein after a 1997 hotel incident during the Sundance Film Festival, tweeted out an alleged email sent from an agent to the actress Lindsay Lohan requesting a hotel “meeting” with Weinstein at the Peninsula Beverly Hills, the site of many an alleged Weinstein attack, for a cameo in an unnamed Scream sequel. The tweet has since been deleted.

While a parade of agents, executives, producers, and assistants were no doubt aware of Weinstein’s appalling behavior, it’s not entirely clear how many actors were—particularly big-name male actors who had, as Lena Dunham so eloquently wrote in the Times, “the least to lose and the most power to shift the narrative, and are probably not dealing with the same level of collective and personal trauma around these allegations.” McGowan charged on Twitter that the actor/filmmaker Ben Affleck, who dated Paltrow from 1997-2000, knew full well about Weinstein’s reputation (McGowan starred alongside Affleck in Phantoms, released by Miramax one year after her alleged hotel incident with Weinstein).

George Clooney, a work friend of Pitt’s, claimed to The Daily Beast that he and many of his high-profile actor friends in Hollywood were unaware of Weinstein’s purported penchant for sexually harassing and assaulting women. “If you’re asking if I knew that someone who was very powerful had a tendency to hit on young, beautiful women, sure. But I had no idea that it had gone to the level of having to pay off eight women for their silence, and that these women were threatened and victimized,” he offered.

But Brad Pitt knew. By his own admission, Paltrow informed him that Weinstein had sexually harassed her all the way back in 1996. While Paltrow explained to the Times how she felt she had to “suppress the experience” of being attacked by Weinstein, and, after being threatened by the exec, went on to act in several other Weinstein-shepherded films (including an Oscar-winning turn in 1998’s Shakespeare in Love), by the late-Aughts Pitt had the power to affect change. He was, as Clooney told Esquire, “the biggest movie star in the world… he’s bigger than me, bigger than DiCaprio.” He ran a successful production company in Plan B Entertainment, responsible for hits like The Departed. And yet, he opted to star in Quentin Tarantino’s 2009 film Inglourious Basterds, which was distributed by The Weinstein Company.

A source close to Pitt confirms to The Daily Beast that Pitt knew of the Paltrow incident with Weinstein but that “Quentin went to him directly to bring him into the project, and Brad did it because of the relationship and the contact. Interaction with Harvey was very limited.” The source, however, went on to explain that since every Tarantino project has been distributed by Weinstein, Pitt understood that Inglourious would be as well. They could not confirm whether Pitt knew at the time of his then-girlfriend Jolie’s alleged incident with Weinstein, and representatives for Jolie and Pitt would not respond to multiple requests for comment on this story.

And, while Pitt’s interactions with Weinstein may have been limited, the exec’s involvement in the project was anything but. Weinstein, who’s earned the nickname “Harvey Scissorhands” for his tendency to demand film edits, usually shies away from meddling with Tarantino movies but was rumored to have demanded that its initial three-hour running time be cut down by at least a half-hour (its final running time: 153 minutes). Weinstein also launched aggressive Oscar campaigns for the film and Pitt, fresh off a Best Actor nod the previous year for The Curious Case of Benjamin Button, doing interview after interview touting their credentials and flooding Academy voters with cheap, non-watermarked DVD screeners. 

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You see, there was a lot riding on Inglourious Basterds. The Weinstein Company was in dire financial straits, having recently hired a high-powered financial advisory firm to restructure after incurring heavy debt. The film’s ultimate success, earning eight Academy Award nominations and grossing over $321 million worldwide, helped keep the company afloat.  

Following the release of Inglourious, Pitt agreed to star in and produce an adaptation of the book Cogan’s Trade, directed by Andrew Dominik and developed by Plan B. After a heated bidding war, the distribution rights to the film were sold to The Weinstein Company, who promised a $20 million ad spend. The film, ultimately titled Killing Them Softly, was released in 2012 by Pitt and Weinstein, earning a meager $15 million stateside. 

Our source in Pitt’s camp said that they were “unable to provide any context” about exactly why Pitt chose to collaborate with Weinstein again on the crime drama (and in a much more involved capacity) despite his ex-fiancée telling him that she’d been accosted by the exec, and that he’d allegedly—perhaps unbeknownst to Pitt, perhaps not—attacked his then-partner Jolie.

The Harvey Weinstein sexual-assault scandal has not only underscored the remarkable courage of the women who chose to come forward, but the cowardice and complicity of the myriad men in power who didn’t.

As Lena Dunham wrote, “Hollywood’s silence, particularly that of men who worked closely with Mr. Weinstein, only reinforces the culture that keeps women from speaking. When we stay silent, we gag the victims. When we stay silent, we condone behavior that none of us could possibly believe is O.K. (unless you do). When we stay silent, we stay on the same path that led us here. Making noise is making change. Making change is why we tell stories. We don’t want to have to tell stories like this one again and again. Speak louder.”