‘Ask E. Jean’ Review: Urgent Documentary Sharply Follows the Pioneering Media Personality Who Sued Trump With Sexual Assault and Defamation Allegations — and Won Twice

For decades, trailblazing journalist E. Jean Carroll had been among the most influential voices in media, penning a dedicated advice column for Elle Magazine until 2019, after countless accolades to her name as a TV host, “SNL” writer, bestselling author and pioneering woman editor at Esquire, Playboy and Outside magazines. Since 2019, after coming forward with her sexual assault and defamation allegations against President Trump, Carroll added not one but two more triumphs to her resume: winning two separate legal battles against the current president through a civil court jury that found him liable for both sexually assaulting Carroll and defaming her. She was first awarded $5 million in 2023 and then, upon re-suing Trump, $83 million in 2024.

With the sharply structured documentary “Ask E. Jean,” director Ivy Meeropol accomplishes the near-impossible, telling the story of Carroll in a manner as consistently enthralling and unapologetic as its subject. How can one possibly fit the multiple electrifying lives that Carroll thrived in into 90-something compact minutes? Throughout her movie, Meeropol shows the way with panache, refusing to limit the main appeal of Carroll to her recent lawsuit wins against Trump. In that, “Ask E. Jean” isn’t at all interested in painting a false sense of victimhood — instead, it succeeds as a celebration of a singularly authentic person, one that beat Trump not only against the odds and in spite of his powers, but also thanks to who she has always been as a truth-teller in the male-dominated spaces of her career.

Meeropol’s approach seems immediately fitting as Carroll spells out her intentions in suing Trump early on in the film. After all, Carroll had built her entire reputation around her brutally honest voice; she wasn’t going to stand for anyone attacking that foundation. Patiently and engagingly, Meeropol takes the viewer through the early days of Carroll’s career, constructing the main details of her life with archival photos and footage (with especially colorful clips from her mid-90s TV program), as well as original on-camera interviews with Carroll herself.

Thanks to editors Leah Goudsmit and Ferne Pearlstein’s perceptive work, a clear picture of the subject quickly emerges. For starters, Carroll always aimed to lift women up, encouraging them to take charge in patriarchal spaces. And with her no-nonsense style of fearlessness, she was always destined for great things in media — less concerned about her starter New York City apartment that had no kitchen or bathtub, but more focused on opportunities that eventually led her to high-profile interviews with the likes of Fran Lebowitz, and brought her face-to-face with icons in the city’s iconic venues like Elaine’s.

And so the once-upon-a-time reader of advice columns rose steadily in her path, landing a job at Elle Magazine on the heels of the unique, gonzo-style journalism work that she did for Esquire. Here, Meeropol lovingly dedicates a healthy slice of the film to a sense of media nostalgia, reminiscing about a time when names like Joan Didion wrote in consumer publications, and a proud editorial process was the valued norm. In one scene, Carroll playfully asks Meeropol, “Does your audience today even know what a magazine is?” It’s a longing, reverent wink at the pre-Substack days of journalism. Back then, she could hold the pulse of America in her hands through the types of questions her readers often asked her.

Still, “Ask E. Jean” isn’t really a movie about the good-old days, knowing all too well that the olden times were not exactly good for certain groups of people, including women. Carroll was lucky to have some role models that she could look up to, including her adventurous, admirably formidable mother. “Being raised by someone like her, I was either going to become a wimp, or a hard-nose,” Carroll reflects, wondering if she became a little bit of both in retrospect. From today’s lens, she is soberly critical of some of the advice she gave back in the ’90s: an era where women were truly coming into their own, questioning whether she was always empowering advice seekers in the right way. Consequently, Carroll confesses that without the #MeToo movement, she probably wouldn’t have publicly shared her allegations of sexual assault against Trump. As such, Meeropol’s film compassionately follows Carroll as she ponders whether she was good at taking the advice that she gave to others for herself. As Carroll puts it, “Do not give the other person the power. Always press charges.”

Thoughtfully weaving together Carroll’s two hearings in 2022 and 2023, Meeropol pieces together details of the events in 1996, when Carroll says Trump raped her in a Bergdorf Goodman dressing room. (Despite being found liable for sexual assault by the jury, and despite the fact that more than 20 women have come out with allegations against the President, Trump has continued to claim that said assault never took place, and that Carroll is “not his type.”) It was a seemingly New York moment when she met him at the department store’s revolving doors, thinking that they were engaging in an enjoyable repartee, before things took a very dark turn.

One of the more disturbing things to emerge from “Ask E. Jean” is not only Trump’s maddening assertion that sexual assault has something to do with a woman’s looks, but also how Carroll had to navigate a similar type of male gaze philosophy before taking a stand in front of the jury. Deep down, she anticipated that the jury might look at her 80-year-old face with doubt if she didn’t look similar to her former self. So for the trial, she hired the same make-up artist from her younger days, just to project an image. In the end, the emotional resonance of Carroll’s story is heartbreaking, especially when she says she kept blaming herself about the assault, all as she would be telling other women, “This is not your fault.” Meeropol goes deep into Carroll’s psyche in these moments, examining what the aftermath of the assault meant for her romantic relationships, marriages and sexual desire.

“Ask E. Jean” is smart in never turning Carroll’s story into a partisan issue, a stance that makes the movie deserving of a wide and urgent release beyond a festival run. Indeed, anyone with a moral compass and reserves of empathy is invited to share Carroll’s feelings —optimism, anger, confusion, joy and all things in between — in light of the facts that Meeropol carefully steers across Carroll’s wins and losses, and various heart-to-hearts with her good friends and her attorney Roberta Kaplan. It’s also worth noting that Carroll still hasn’t seen a single dime of her $88 million total win. (Her future spending aspirations remain as selfless as opening a support center for women, and as modest as buying a good toaster.) And she lost her long-standing post at Elle amid the legal battle. (The magazine claims they just made a business decision unrelated to Carroll’s lawsuits against Trump.) But to Carroll, it was always her name and reputation that mattered the most, anyway. Watching her defiantly claim both is what makes “Ask E. Jean” a most rewarding experience.