Ask E. Jean

by Mike McGranaghan

Long before she successfully sued Donald Trump for sexual assault, E. Jean Carroll was a famous advice columnist. She had her own live television show for a few years in the ‘90s, where she gave no-nonsense guidance to women with relationship issues. Even without the Trump angle, she’s a fascinating subject for a documentary. Ask E. Jean looks back at her illustrious career and, yes, her eventual legal victory against an American president.

The one-time Miss Cheerleader USA grew up to become a practitioner of “gonzo journalism,” a format pioneered by Hunter S. Thompson - whose biography she penned - in which the author writes less about the story itself and more about their own reaction to the story. Success in this realm led her to become the first female editor at Esquire and Playboy. In 1993, she was given a chance to pen an advice column for Elle magazine, a gig that turned her into a frequent talk show guest and host of her own nightly show.

With a sharp wit and a penchant for straight talk, Carroll provides plenty of enlightening stories about her career. Director Ivy Meeropol wisely lets her subject speak, knowing full well that E. Jean's personality helps convey the importance of her professional journey. What comes across most strongly is that American women were facing a new series of concerns, and Carroll’s strong feminist perspective was just what the doctor ordered in terms of helping make them public. The film proves to be an inspiring portrait of the art of breaking glass ceilings.

Ask E. Jean points out that Carroll frequently advocated for women to stand up to men and to report assault, yet she was initially too afraid to report Trump’s abuse of her in a dressing room at the Bergdorf Goodman department store. She knew her name would be dragged through the mud, that people would rally around the man. Carroll acknowledges that irony, explaining how the #MeToo movement inspired her to take the advice she gave so many others. Footage from her deposition, in which she describes the assault in sickening detail, will leave you rattled.

There might be a tendency among some people to assume the documentary is heavily anti-Trump. E. Jean Carroll certainly (understandably) is, but Meeropol’s intent is less overtly partisan. She aims to explore how Carroll’s past perfectly set her up to take on Trump. The movie celebrates the power and courage of women who speak up, knowing sexual assault is an uncomfortable topic and that there’s an overall societal desire to sweep discussion of it under the rug.

Ask E. Jean is deadly serious on that count, although there are plenty of funny moments, too, courtesy of Carroll’s colorful persona. That makes it one of 2026’s most indispensable non-fiction films.