E. Jean Carroll, the decades-long advice columnist, has become a figure of resilience in her prolonged legal battle against Donald Trump. Her story, marked by accusations of sexual assault dating back to 1995-1996 in New York City, culminated in two successful court cases—one for defamation and another for sexual assault—that awarded her nearly $90 million in damages. This compelling journey is now the subject of “Ask E Jean,” an official selection of the Telluride Film Festival, directed by Ivy Meeropol. The film offers unprecedented access to the intricate process behind the Carroll-Trump conflict, even as Trump continues to appeal both cases.

Meeropol, whose unique background includes being the granddaughter of Julius and Ethel Rosenberg and having previously examined Roy Cohn, one of the architects of Trump’s rise, brings a distinct perspective to the documentary. Her aim was to tell E. Jean’s entire story, not merely focus on the assault, to help audiences understand the broader context. The film distinguishes itself by including never-before-seen footage of Carroll’s harrowing deposition, led by Alina Habba, Trump’s attorney. Carroll described Habba as “magnificent,” “effervescent and super smart,” yet also “brutal,” likening her questioning during the seven-hour first deposition to a “1700s” case, repeatedly probing whether Carroll screamed during the alleged assault. These difficult-to-watch scenes, showcasing the pre-trial “torture,” are expected to astound viewers, particularly women.

Beyond the legal drama, “Ask E Jean” also explores Carroll’s remarkable legacy as a pioneering female gonzo journalist, a syndicated TV host (under Roger Ailes), and an advice guru. A significant part of the film, and Carroll’s candid reflections, addresses her past professional advice to women. She openly admits that about fifty percent of her answers, particularly regarding women in the workplace, were “bad.” Advice such as “suck it up and get on with it,” “use your looks,” or to “not make a fuss” if a man behaved inappropriately, she now deems “exactly wrong.” Carroll contrasts this with her current conviction that women should “Stand up and scream,” believing it could have sparked a revolution if advised earlier. However, Meeropol highlights that Carroll’s syndicated TV show in the ‘90s, while offering problematic workplace advice, also empowered women by advocating for independence, education, passion, and work, challenging traditional roles.

The documentary’s release comes at a critical time, with Meeropol and Carroll asserting its importance amid a “feeling of suspension” and fear in the current political climate. Despite speculation about difficulties in finding a buyer due to media companies’ fears of Trump’s retaliation, Carroll insists they are “flying” in terms of interest. Meeropol believes the current atmosphere, marked by Trump’s ongoing “damage” and signs of authoritarianism like repression of women and censorship, makes people actively “looking for something to feel that there’s a way out of the madness.”

Carroll remains resolute in the face of ongoing “sludge of garbage” and threats, stating she is willing to pay the price and doesn't care if someone shoots her, embracing the challenges inherent in being an artist. She attributes Trump’s current silence regarding the documentary to his ongoing appeal before the United States Court of Appeals Second Circuit, confidently stating he will have to pay her substantial sums regardless of his behavior. Meeropol also faced challenges during filming, with Carroll’s lawyer, Robbie Kaplan, advising her to stop filming several times as footage could be used as evidence during the trial, leading Meeropol to capture footage resourcefully with limited equipment.

Interestingly, Carroll shares a positive personal and professional history with Roger Ailes, the disgraced media executive, describing him as a “great broadcaster,” a “great boss,” and “one of my best friends.” She expresses astonishment at the “cesspool” that was hidden beneath his public persona. As for her current endeavors, Carroll admits to being in a “horrible stage” with her writing, unsure of her next project. Yet, she maintains her characteristic vigor, asserting that she “grabs that motherfucker” whenever joy appears in her life.