“If you were concerned about being dragged through the mud,” asks lawyer Alina Habba, “Why would you choose to sue Donald Trump?”

Calm and composed, E Jean Carroll removes her glasses and replies firmly: “Because he called me a liar. He called me a liar. And I couldn’t let it stand.”

Carroll’s private deposition from 2022 is made public for the first time in Ask E Jean, a documentary by Ivy Meeropol about a woman of strong character, deep resilience and sharp wit who refuses to be cast in the role of victim or bit-part player in the Trump cinematic universe.

Carroll, 82, a journalist, author and advice columnist, is the only woman to beat Trump in court, a feat she accomplished not once but twice. In 2019 she alleged that he raped her in a dressing room at a department store in Manhattan in the mid-1990s, leading to two blockbuster court cases.

Ask E Jean examines the question of why she waited decades to come forward and makes a convincing case that she belongs to the “silent generation” – a cohort of women who were conditioned to endure the predatory behaviour of men with a shrug and a smile.

“I was born in 1943,” she explains in the film. “We are the chin-up, move-it-on, grin-and-bear-it generation. We didn’t complain. It would never occur to me. We actually smiled about it and moved on. That’s how we handled things.”

Carroll is a former Miss Indiana University and Miss Cheerleader USA who became the first female contributing editor at Playboy magazine and wrote the feisty “Ask E Jean” column for Elle from 1993 to 2019. She hosted her own cable TV show, wrote for one season of Saturday Night Live and penned an unauthorised biography of fellow gonzo journalist Hunter S Thompson.

When Trump sexually abused her in a dressing room at Bergdorf Goodman, Carroll did what countless women of her era did, confiding in trusted friends – the author Lisa Birnbach and television journalist Carol Martin – and then buried the memory deep down. And her initial reaction, attempting to laugh it off, has frequently been weaponised against her.

Meeropol handles this with empathy, showing how laughter served as a desperate shield. “She is unapologetic and so many women will recognise that in themselves,” she says via Zoom from her home in Cold Spring, New York. “Of course, you can try to laugh because it’s – ‘Wait a minute, what’s happening here? I don’t want this person to get angry.’ It makes perfect sense but it gets so warped by how we talk about these things.”

Carroll’s journey to the courtroom was not premeditated. She initially penned a list of “hideous men” – including Trump – because the #MeToo movement had deeply affected her, and her readers were begging for guidance on whether to come forward with their own stories of abuse.

It was Trump’s reaction that lit the fuse. Standing on the White House lawn, the US president – who has been accused of sexual misconduct by an estimated 27 women, something he has denied – branded her a liar and “whack job” and insisted she was “not my type”. For Carroll, who had spent decades building a career on her credibility and wit, the relentless defamation was intolerable.

She teamed up with Roberta Kaplan, a civil litigator described by peers as a “street fighter” and a “force of nature”. In 2023 a jury found Trump liable for sexual abuse and defamation but did not determine that he raped her, awarding Carroll $5m.

During his deposition, Trump was shown a photograph from 1987 of himself with his first wife, Ivana Trump, and Carroll and Carroll’s then husband, John Johnson, at a public event in New York. Trump misidentified Carroll as his ex-wife, Marla Maples, undermining his “not my type” defence.

In 2024 a second jury awarded Carroll $83.3m for defamation regarding Trump’s continued social media attacks – intended as a punitive measure to deter him from further defamation. But Trump’s lawyers are seeking to overturn the rulings and Carroll has not yet received a cent.

Carroll says in the film: “When I accused Donald Trump of sexual assault, I had no idea what I was in for. The avalanche of slime has been unbelievable.”

In that context, getting her to agree to a documentary required the kind of dogged persistence that Meeropol, 57, has honed over a career exploring the intersections of personal lives and political forces. Initially, Carroll wanted nothing to do with it.

“I was lucky because she basically told everybody – I’m not going to use an expletive – but the line that she relayed from her agent to my manager was, ‘I’d rather eat my shoe.’ I find it very funny because it’s classic her.”

The breakthrough came when a mutual friend persuaded Carroll to watch Meeropol’s acclaimed HBO documentary Bully. Coward. Victim. The Story of Roy Cohn, about the notorious lawyer who mentored the young Trump and prosecuted Meeropol’s grandparents, Julius and Ethel Rosenberg. A Zoom meeting followed, the connection was immediate and Carroll declared: “All right Ivy, let’s do it.”

Meeropol discovered a woman who is still energetic, eccentric, funny, generous in her support and, despite her status as a public figure who belonged to New York’s media elite, protective of her solitude. “She needs her time alone; she’s a writer; that’s what she loves to do. She likes to be in her cabin with her dogs, drinking her tea and writing or reporting. A lot of what she had to endure with the trials and all the publicity was very hard for her.”

But securing funding for the project proved harder. Financiers and studios repeatedly turned the film down, blaming Trump fatigue, too many #MeToo films or Carroll not being famous enough. “I was surprised and disappointed,” says Meeropol. “I thought, we’ve got the most incredible character in documentary history, possibly.”

The film eventually secured independent equity investment in 2023, with a budget of less than $2m. Meanwhile Meeropol and her team had been digging through Carroll’s packed storage unit and the basement of her home, rescuing boxes of dusty VHS tapes.

“The very next day she called me and said, ‘You’re not going to believe this. The basement flooded.’” The rescued tapes, along with 25 further episodes unearthed by NBCUniversal, yielded footage of Carroll’s 1990s television show, broadcast on the America’s Talking cable network, run by Roger Ailes.

Watching the footage, Meeropol was struck by how radically progressive Carroll’s advice was for the era. “She is giving incredible advice at a time when women were not hearing that. Like, ‘You don’t have to be married at 30. Who told you that? Don’t beat yourself up because you’re not married at 30. If you’re bored at home because your husband goes off to work and you drop your kid off at school, go to college.’

“It’s so interesting to see because it’s such a time capsule moment in the mid-90s. As E Jean says, women were finally talking about their careers and what they want to do with their lives, which was not something she’d experienced except that she was this outlier who had paved her own way when she got to New York City and launched her career in the male-dominated magazine world.”

Meeropol was determined not to frame Carroll as a victim. “She rejects those terms herself – even ‘survivor’. I’m at a loss sometimes what language to use because it’s so current but she embodies the opposite of that. That’s what Gisèle Pelicot [a Frenchwoman who waived her right to anonymity as the victim in a multiple rape case] has been talking about and the Epstein survivors coming out: shame has got to switch sides.

“I thought about that a lot with E Jean. She herself embodies the flip side of shame because she will sit there and say, yeah, I was flirting with Donald Trump, I did try to laugh it off and I do love men. It’s refreshing. The worst thing for her would have been – she says it in her show when she’s talking to a young woman who is talking about being raped – is to make yourself the victim.”

Meeropol hopes the documentary speaks beyond one woman’s experience. “We can’t let these stories be buried,” the director insists. “The Trump administration or whoever is hiding in the Epstein files? I’m sick of it and E Jean is too. Many of us, men and women, are fed up so put things out and show the truth.”

• Ask E Jean is playing in New York now and will open in Los Angeles on 29 May with a UK date to be announced