Ask E. Jean

E. Jean Carroll broke into the business when a literary quiz she wrote about Ernest Hemingway and F. Scott Fitzgerald was published by Esquire magazine. They brought her to New York City to write a piece on Fran Lebowitz and, falling in love with the city, she never left. She branched out, becoming a friend and fellow practitioner of 'gonzo journalism' with Hunter S. Thompson. Known for her writing on sex and gender issues, she became the first female contributing editor of Playboy. In 1996, she had her dream job as a television advice columnist. Even Donald Trump recognized her from her show, "Ask E. Jean."

Laura's Review: B+

Cowriter (with Leah Goudsmit and Ferne Pearlstein)/director Ivy Meeropol ("Bully. Coward. Victim. The Story of Roy Cohn") may begin with what most know Carroll from today, her two successful lawsuits against Donald Trump for sexual assault and defamation, but there is a whole lot more to E. Jean Carroll, who would still be an intriguing documentary subject even if she'd never met the man. Now 80, E. Jean is still quite the character and clearly was a live wire back in the day. She was also of a generational mindset, one that accepted sexism as part of the business landscape. Now Carroll disavows many of her views of the past, but Meeropol doesn't hesitate to contrast her thirty year-old advice with current mores.

The documentary opens with E. Jean arriving in court for the first trial against Trump, then explaining why she sued him in pre-trial video interview with his lawyer Alina Habba (who Trump later attempted to install as New Jersey's D.A.). 'He called me a liar and I couldn't let it stand.' Sitting in a restaurant booth with Lisa Birnbach, an old writing colleague who is now a close friend, the two recall how E. told her about her encounter with Trump in a Bergdorf changing room right after it happened, expecting her to laugh and getting quite a different reaction. She also told a television colleague, Carol Martin, who, at the time, advised her to say nothing because she'd be crushed by Trump's lawyers.

It is surprising to hear Carroll retell this story years later, as initially she was having a good time, indulging in what she thought a flirtation that would make a good anecdote later. Trump saw her leaving the store, put his hand up to stop her and said 'you're the advice lady,' then asking her to give him advice buying a gift for a woman. As Birnbach points out, she was more famous than he at the time. Everything about Carroll seems genuine, the woman never trying to paint the experience as more than it was, although it did turn grim. That, along with the fact that Trump, who denigrated Carroll's appearance claiming she was not 'his type,' identified her in a picture as his second wife, Marla Maples, is what enabled lawyer Roberta Kaplan to win the case. When Trump continued to defame Carroll after that, Kaplan famously won again, asking the jury to consider just how much money it would take to get him to stop. Carroll was awarded over $83 million in addition to the $5 million she got from the first trial in 2019 (Trump is still appealing and Carroll hasn't received a cent).

But that's only part of the story and Meeropol captures her subject in a cafe, at home and via snippets from her television show relating her experiences, like how the militant lesbian pornographers she interviewed in San Francisco were a fun bunch of folk or how Hunter S. Thompson lived 'in a state of grace,' the man fearlessly driving 90 mph on mountain roads without headlights. Her advice from the time can be cringe worthy now, telling women not to allow themselves to be victimized by men, and, even worse, 'always press charges,' something she famously did not do at the time. Now she marvels at the fact that she had to be made to appear 'f*&able' at 80 for her trial appearance, stylists recreating her look from back in the 90's, while also noting the demeaning questions asked of her by Habba (did she wear underwear, had she been drinking, taken drugs, taken acting classes, etc.). She was also inundated with horrible messages and threats by the MAGA faithful.

In the end, Carroll triumphs, though, glamming up to walk the Time 100 celebration red carpet with Roberta Kaplan, her 90's self leaving us with the worthy advice 'Fate favors the fearless.' "Ask E. Jean" jumps off from a scandalous lawsuit to examine a full and flavorful life.

Robin's Review: B+

E. Jean Carroll has two claims to fame: she had an advice column in Elle magazine and companion TV program for 23 years. She also sued Donald Trump – twice and won both times to the tune of $88.3 million – for defamation of character and sexual assault and continues to suffer the wrath of Donald, without payoff, in "Ask E. Jean."

This is an enigmatic documentary of an enigmatic person whose claim to fame was one of the long-running advice columns. In both print and on TV, she always encouraged her writers/callers and coached them all, if sexually abused, to report it and get it on the record. E. Jean, though, did not follow her own advice because "no one would have believed me." (Just as an aside, is this not the reason that most rapes and sexual assaults go unreported? Just asking, E. Jean.)

As I have always said, a documentary should entertain, teach and enlighten and director Ivy Meeropol accomplishes all three, chronicling Carroll's long career. Beside the advice column in Elle magazine, she also had a call in show, "Ask E. Jean," from '94 to '96, was a writer on SNL in 1987, writer for The Atlantic and Vanity Fair and contributing editor at Esquire, New York and Playboy – also the first female (editor) at Playboy. She also authored a biography of Hunter S. Thompson and considered herself a "gonzo" journalist, too, though a very femme version.

All this success was blunted by her brief encounter with the future president of the United States and that is where the hate of that man entered her life. It is sad that a woman who has such a long and successful career as a writer, journalist and advice columnist has a claim to fame that involves THAT! E. Jean deserves better.

Abramorama released "Ask E. Jean" in select theaters on 5/22/26, expanding in subsequent weeks.  Click here for theaters and playdates.