Director R.J. Cutler on getting Martha Stewart, Elton John to open up in new documentaries: 'You've got to earn their trust'

Director R.J. Cutler says “trust” is among his secrets to getting Martha Stewart, Elton John, Billie Eilish, Anna Wintour and other famous people to open up in his documentaries. But he’s found that people really “want to tell their stories.”

Martha — his film about the lifestyle queen’s ascent, descent and reinvention — is now streaming on Netflix. Stewart warned Cutler it was not going to be easy for her to open up, but there she is onscreen spilling about affairs she had during her marriage seemingly without an iota of regret.

Elton John: Never Too Late, which Cutler directed with John’s husband, David Furnish, follows Dec. 13 on Disney+ and looks back at the British singer’s storied music career amid his 2023 retirement from touring. All the layers get pulled back on the larger-than-life, bedazzled, bespectacled personality and it’s so humanizing watching him backstage, in his bathrobe and socks, having his makeup applied for one of the last times on the road. Even more so when the septuagenarian discusses his mortality or shares his young sons’ fears of him dying.

“I like to tell great stories and that’s what I see in common with Martha and Elton and Anna and Billie,” Cutler, who also helmed The September Issue (2009) and Billie Eilish: The World's a Little Blurry (2021), told Yahoo Entertainment. “I don't see them as guarded. I see them as having really fascinating stories to tell.”

Cutler said the “desire to have your story told is the most natural thing in the world” — and “no less so for people I’ve made movies about.”

It starts with connecting with his subjects.

“You’ve got to earn their trust, of course,” he said. “You gotta listen,” “be empathic” and also “resourceful.”

And remember that it’s their story. It’s merely on “loan” to him.

John opening up on camera about mortality 'is what this journey is about'

Sometimes movie magic unfolds in candid conversation — like when John speaks rawly about his mortality as it stares him in the face.

“Elton talking about his mortality is … the film reaching its hand out to you to say: This is what this journey is about,” said Cutler.

He continued, “This is the journey of an extraordinary man. Late in life. He's got young children. He's found happiness. He found happiness in large part because of this incredible risk he took when he was a young man to come out” in 1976. “Now he's facing this consequential decision: How does he want to spend the remaining years of his life? And Elton has chosen to spend them focused on family — not focused on career, not focused on fame, not focused on what's really the last addiction of his life, which is performing.”

For the record, John’s touring retirement has stuck.

“I saw him last night … and I said: Are you missing it at all?” Cutler said. “He said, ‘Zero. Zero.’”

Stewart’s archive had answers when she didn’t

Cutler is always looking for alternatives in filmmaking, so it’s not built entirely around talking head interviews.

In Martha, because she’s telling her story for the first time, she’s the only on-camera interview in the doc. Others giving commentary — from her daughter Alexis to her publicist — are audio only. Doing it that way elevates Stewart’s voice and story.

But Stewart isn’t someone who wants to spend a lot of time reflecting on the past. Even at 83, she’s looking ahead to what’s next. So having access to the lifestyle guru’s personal archive (photos, letters, footage) for the film was better than Stewart sharing her recollections in some instances, Cutler said.

“I'd rather have her letters to her husband during the final years of their marriage than her talking about it,” Cutler said. “She really is revealed in those letters. I'd rather have her prison diaries written in the moment, as we do. I'd rather have … the footage nobody had seen [recorded] in the weeks between her conviction and her sentencing where you see how incredibly vulnerable she is as she prepares for prison. She tells us: You go to the dentist. You go to the gynecologist. You get your body in shape for what might come. That's powerful stuff.”

For John’s doc, a centerpiece was getting access to audio conversations the singer had with ghostwriter Alexis Petridis for his 2019 memoir, Me. In Eilish’s film, Cutler encouraged the singer’s mother, Maggie Baird, to shoot video on her iPhone.

“Maggie's a brilliant cinematographer, it turns out,” Cutler said. “She's as brilliant a cinematographer as her children are musicians, and that footage was incredibly valuable to us. So, you know, you gotta be resourceful, but this is how we do what we do.”

Wintour provided 'a window into who she was' with a few words

Cutler’s listening skills opened the door for memorable parts in The September Issue about the ultra-private Wintour’s relationship with her family.

The filmmaker said he has conversations with all his subjects early on about him having final cut, which he says is essential for the film “to be taken seriously.” He recalled having that conversation with the Vogue editor on the day they met.

“Anna said, ‘My father was a journalist. I'm a journalist. That's not going to be a problem,’” Cutler said. “I thought to myself: Great. I always like to get that out [of the way] as early as possible. … [Then] when I was reflecting on the conversation later that night, I thought: ‘Why did Anna Wintour mention her dad to me? … Was it to impress me? Was she providing a window into who she was?’ I thought: I’ll keep this in mind.”

On the final day of filming, Cutler brought it up. It led to Wintour revealing how her successful siblings, with careers one more brilliant than the next, are “very amused by what I do,” as if her job wasn’t on par with their professions.

“That connection revealed so much,” Cutler said. “Here was this incredibly gifted woman who runs the multibillion dollar international fashion industry, as she has for decades, and who struggled with whether her family took her seriously. … So that's part of it. You gotta be a good listener."

'The story belongs to the subject'

Cutler — who’s currently making a World Series documentary — says it’s “all about earning trust” with his subjects. One way to do that “is to be who you say you are.”

“If you say, ‘We have a tiny footprint. It's just me and a camera and sound, don't show up with 30 people,” he said. “And if you are going to have a crew, make sure that everybody knows and that they're comfortable and that you do know their areas of sensitivity. … It's like any relationship. You want to be a good partner.”

Cutler was schooled in the how-tos of the genre working for “documentary legends” Chris Hegedus and D.A. Pennebaker early in his career on 1993’s The War Room, which was about Bill Clinton’s 1992 presidential campaign.

“I learned from them that the story belongs to the subject,” he said. “The subject is trusting you to tell the story. They loan you the story.”

He continued, “You want to hear them. We always say: It's better to stop shooting 10 minutes before someone says, ‘I'm tired. Can we stop for the day?’ And especially when we're filming over long periods of time, we make sure to take weeks off. You'd rather they miss you than wish you’d go away.”

Martha is now streaming on Netflix. Elton John: Never Too Late premieres Dec. 13 on Disney+.