The Best Documentaries of 2019 (So Far)

From the competing Fyre Fest docs to news-breaking investigations into Michael Jackson and R. Kelly, it's been a banner year for documentaries.

You know it's a good year for documentaries when two docs about the same subject stir up incredible buzz. 2019 is the year that brought us the competing Fyre Fest docs, as well as news-breaking investigations into pop stars R. Kelly and Michael Jackson, plus an unbelievable deep dive into alleged scammer Elizabeth Holmes. Here are the best documentaries of 2019 ... so far.

Leaving Neverland

While there have been reports of alleged abuse by late pop icon Michael Jackson for decades, in this two-part HBO documentary, two of his accusers share their emotional, detailed, and disturbing accounts. Wade Robson and James Safechuck met Jackson when they were 7 and 10, respectively, and they and their families open up to filmmaker Dan Reed about years of alleged sexual abuse in Leaving Neverland.

Fyre Fraud

You could say one doc about the disaster that was the Fyre Festival would be enough—but you'd be wrong. In Fyre Fraud, the Hulu one, festival mastermind Billy McFarland sits down for an interview with the filmmakers who ask him point-blank about his lies and the crimes he committed to cover up the fact that the music festival he orchestrated was a poorly planned disaster. McFarland dodges nearly every question, but it's still fascinating to watch him respond.

Fyre: The Greatest Party that Never Happened

The Netflix version of events is a more sober look at the effects and aftermath McFarland and this festival had on ticket holders and the people in the Bahamas who helped put the event together. Plus, the Netflix film has the unforgettable interview with McFarland's business partner, Andy King, who offered to go far and beyond the call of duty to get some boxes of Evian water bottles past customs.


Surviving R. Kelly

Like Jackson, there had been years of allegations against singer R. Kelly—even resulting in a trial. But in the Lifetime docu-series Surviving R. Kelly, filmmaker dream hampton speaks with the women who say they suffered abuse for years. In the case of the women still living with the singer, Hampton speaks with their family members, even filming one mother trying to convince her daughter to come home.

Ask Dr. Ruth

Everyone knows Dr. Ruth, the iconic sex therapist who has been doling out advice for decades. But in this intimate Hulu documentary, Ruth Westheimer gets personal, talking about losing her parents in the Holocaust, her path to fame, and her own relationship with sex.

The Inventor: Out for Blood in Silicon Valley

It's impossible to look away from the story about Elizabeth Holmes, the founder of blood-testing technology company Theranos, who went from the tech industry's darling to a pariah in just a matter of years, after it was discovered her company was faking medical test results. This HBO doc features interviews with those who saw the collapse first hand like whistleblower Tyler Schultz.

Conversations with a Killer: The Ted Bundy Tapes

Before Zac Efron's portrayal of serial killer Ted Bundy in Extremely Wicked, Shockingly Evil and Vile, this doc told the real story. Conversations with a Killer was created by Joe Berlinger, the same person who made Extremely Wicked. For the Netflix doc, Berlinger interviewed journalist Stephen Michaud about his revealing conversations with Bundy while he was in prison.

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The Black Godfather

This Netflix doc looks at the life of Clarence Avant, who grew up in the segregated south and went on to become a hugely influential music executive and film producer. Director Reginald Hudlin interviewed more than 75 people over three years. "There's the power that needs the spotlight," Barack Obama says of Avant, "and there's the power behind the scenes."

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Kate Storey
Kate Storey is a Writer-at-Large for Esquire covering culture, politics, and style. She spent two years as Hearst Digital Media's News Director, managing an international shared news desk. Her book, White House By the Sea, about the Kennedys in Hyannis Port, is out summer 2023.
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