Director Alex Gibney looks back on a career of profiling liars and shady characters, from Elizabeth Holmes to Lance Armstrong, and crowns the most despicable

Axel Schmidt/AP Photo; Seth Wenig/AP Photo; Greg Allen/Invision/AP; Anthony Devlin/Reuters; Paul Sakuma/AP Photo; Samantha Lee/Business Insider(L-R) Dick Cheney, Steve Jobs, director Alex Gibney, Elizabeth Holmes, and Julian Assange.

For close to 40 years, Oscar-winning documentary filmmaker Alex Gibney has made movies about some of the most complex and controversial figures of the last century.

He’s examined the maddening drive of Steve Jobs (“Steve Jobs: The Man in the Machine”), the bald-faced lies of people like Lance Armstrong (“The Armstrong Lie”) and Julian Assange (“We Steal Secrets: The Story of WikiLeaks”), and even the mind games done by the head of Scientology, David Miscavige (“Going Clear: Scientology & the Prison of Belief”).

Now you can add to the list disgraced Theranos founder, Elizabeth Holmes, the subject of his latest documentary, “The Inventor: Out for Blood in Silicon Valley.”

So what attracts Gibney to do movies on people like these?

“Abuse of power,” Gibney told Business Insider. “The way that power gets abused is sometimes appealing to people’s sense of idealism. Then that allows a kind of latitude we otherwise wouldn’t give them. They blind us.”

Here Gibney looks back on some of the shady people he’s made movies about over the years, and says who is the most despicable:

Elizabeth Holmes — “The Inventor: Out for Blood in Silicon Valley” (2019)

Courtesy HBOTheranos founder Elizabeth Holmes at the company’s headquarters.

Like many of the people on this list, Holmes falls into the group that Gibney described as “prisoners of belief.” These are people who are so sucked into their “cause” that they can convince others to join them and can’t see the wrong being done.

“Her goal was so high minded and she fell so far so fast, to me it seemed like a good opportunity to explore the psychology of fraud,” said Gibney on what fascinated him about doing a movie on Holmes. “Not only how somebody like Elizabeth deceives herself but how she deceives investors and journalists and customers.”

Lance Armstrong — “The Armstrong Lie” (2013)

Getty ImagesSeven-time Tour de France winner Lance Armstrong.

In this documentary, Gibney first set out to make a comeback film about Armstrong’s return to cycling after retiring in 2005. Then the movie changed after the cancer survivor and seven-time Tour de France winner was hit with a lifetime ban from the sport following a doping investigation. Gibney’s movie became a search for answers from Armstrong. But like Holmes, Armstrong is too much a prisoner of belief.

“Lance could stand up after a race and say, ‘How dare you say that I, as a cancer survivor, would ever use performance enhancing drugs.’ And I think in the moment he said that he believed it,” Gibney said. “But then he would get off the stage, go into the bus, and do a bag of blood. So it wasn’t like he was unaware of the cheating that he was doing, he just felt that in that moment that was a lie that everybody wanted to believe so badly he could say it as if it were true.”

Julian Assange — “We Steal Secrets: The Story of WikiLeaks” (2013)

Gibney looks inside what led to the birth of WikiLeaks and in doing so discovers the dark side of its creator: from sexual assault allegations to the time Assange abandoned whistleblower Chelsea Manning, who was imprisoned for seven years for providing WikiLeaks with what is believed to be the largest release of state secrets in US history.

“Assange is the perfect example of the prisoner of belief, he believed that what he was doing was so good that he was entitled to do anything,” Gibney said. “The truth is that Assange knew damn well who Bradley Manning, now Chelsea Manning was. But pretended that he had this anonymized leaking machine, which prevented him from knowing the identity of the leaker. That just wasn’t so. He knew the identity of the leaker and then when the leaker needed him most he deserted her.”

Steve Jobs — “Steve Jobs: The Man in the Machine” (2015)

YouTube/Magnolia PicturesApple co-founder/CEO Steve Jobs.

The founder of Apple was what Holmes aspired to be, but Gibney said there was a big difference between the two.

“The storytelling was more important than anything else to Jobs, and that was his great power,” Gibney said. “He could weave a tale of idealism about Apple, even as Apple did some ruthless things. But at the end of the day the very lesson that Elizabeth should have known about her hero ruined her. Jobs comes back out of the failure of NeXT with an understanding that he has to surround himself with people who are more talented than he is and he needs to be able to listen to them even if they criticise him – instead of hearing only the good news, like Elizabeth wanted to hear. He’s willing to hear the bad news so that he can correct and make things better. That was a key lesson Elizabeth never learned.”

David Miscavige — “Going Clear: Scientology & the Prison of Belief” (2015)

As Gibney shows in his gripping documentary, Miscavige was the puppet master for all the shadowy actions of the Church of Scientology – especially pushing forward the attacks on those who spoke out against it. This is the movie where Gibney births the phrase “prison of belief,” and it’s clear why.

“He would do anything to vilify or undermine people who come after the church or criticise the church in his view, so that is the prisoner of belief,” Gibney said. “And the prisoner of belief in that story is also many of the people in the Church of Scientology who learn of the abuses but don’t leave the church. It’s like they are a prisoner in which the door to the cell is open but they can’t leave. Because for them to leave would be to admit that they have been captured by a poisonous belief system that forced them to attack their own families.”

Dick Cheney — “Taxi to the Dark Side” (2007)

“The worst is the one you haven’t mentioned, which is Dick Cheney,” Gibney said when asked who out of these people is the one he feels is the most despicable.

In Gibney’s Oscar-winning doc, he explores the US torture policies after 9/11, which Cheney was one of the chief architects of. “Dark Side” in the title refers to what Cheney said on “Meet the Press” days after the attacks on September 11: “We have to work on the dark side, if you will,” he said. “We’re going to spend time in the shadows.”

“Here’s a guy who thought the torture was justified in the service of protecting the American people,” Gibney said. “By protecting the American people through torture he basically transgressed on the very principals that we hold in highest esteem.”

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