“Remember this moment, because it’s a hit—and they don’t come along very often,” Nora Ephron reportedly said the night her 1998 film You’ve Got Mail premiered. Her words rose from experience. While the acclaimed reporter turned filmmaker is remembered for creating some of the best romantic comedies of all time, including When Harry Met Sally… and Sleepless in Seattle, Ephron was also no stranger to a flop.

It is the unavoidable truth nestled within Nora Ephron at the Movies, a new book devoted to the writer-director’s career, written by Ilana Kaplan (a past Vanity Fair contributor): Most of Ephron’s films didn’t work.

Ephron’s filmography was bookended by success. She earned an Oscar nomination for her first feature-film screenplay, Silkwood, directed by Mike Nichols and starring Meryl Streep. Streep also got an Oscar nomination for Ephron’s final film, Julie & Julia. But you’d be forgiven for forgetting some of her other titles, like 1989’s father-daughter mobster comedy Cookie, or the 1996 John Travolta vehicle Michael—a movie that made more than that year’s Jerry Maguire in its opening weekend, but has otherwise evaporated from public consciousness. Ephron also helmed not one, but two Steve Martin bombs (1990’s My Blue Heaven, for which she wrote the screenplay, and 1994’s Mixed Nuts, which she wrote and directed), showing how the sardonic voice of her essays didn’t always translate to film. Her seminal debut novel, Heartburn, which recounted the end of her marriage to Washington Post Watergate reporter Carl Bernstein, had a similarly rocky transition to the screen: The adaptation, starring Streep and Jack Nicholson, was met with a far chillier reception than the book had received.

“Failure, they say, is a growth experience; you learn from failure. I wish that were true,” Ephron wrote in her 2010 book, I Remember Nothing. “It seems to me the main thing you learn from a failure is that it’s entirely possible you will have another failure.” But while she was well aware of her misfires, they didn’t stop Ephron, who “did not want to just be seen as a rom-com queen,” Kaplan tells Vanity Fair. “That is a part of her identity, but I don’t think it’s her full identity.”

Kaplan, who was introduced to You’ve Got Mail as a nine-year-old and later referenced the filmmaker in her own wedding vows, admits to falling for the popular conception of Ephron. “Honestly, I romanticized my whole life,” she says. “I thought that I was living a rom-com and that every year on Christmas—I’m Jewish, by the way—I would meet my husband. I was totally delusional.”

Yet it is Ephron’s own contradictions—an iconic filmmaker with more misses than hits, an often prickly person now forever associated with coziness—that have kept people fascinated even more than a decade after her 2012 death. “Her life is boiled down to the equivalent of one of her rom-coms. But Nora’s work wasn’t always loved—it was often divisive, reviled, and written off by critics,” Kaplan writes. “Of course, there have been some reappraisals over the years, but the conflation between the adoration for Nora and her work remains.”

Vanity Fair: You come to the conclusion that Nora’s “everything is copy” credo was less about divulging everything than shaping one’s own narrative. What was vital to you in telling the story of Nora?

Ilana Kaplan: I wanted to capture how she revitalized the rom-com genre, how she was progressive in certain ways, but there were also blind spots in her work because of the time, because of her social status. I wanted it to be largely a celebration of her work, but it was important to really grapple with things that might’ve been problematic in it. There are barely any people of color in her movies. You can count the ones that you’ve heard of on one hand, or they’re just side characters like Dave Chappelle in You’ve Got Mail. If you’re looking at a movie like Mixed Nuts, in some ways you could be like, oh, this is progressive because there’s a trans character in it, but it’s pretty transphobic. You can celebrate the way that she pushed the genre forward by also critiquing what she could have done better.

It was also important to me, as much as her rom-coms are celebrated, she has all this other work that maybe the mainstream doesn’t really know. When I was putting the book together, I didn’t realize she was involved in a movie called Cookie, which is a campy mob movie directed by Susan Seidelman. It’s a deep cut for most people. Silkwood is a revered movie, but it’s not available online anywhere. You have to order the DVD or get it from your library. Sometimes that’s forgotten in the streaming age. So it’s fun to really dig into those movies and remind people that they exist.

The 42 Best Romantic Comedies of All Time

The third part for me was—and I always go back to Rachel Syme’s piece in The New Yorker—that with history, we’ve kind of conflated Nora with her rom-coms, that she was this sentimental, sweet figure. But she could be pretty biting and had a wry sense of humor. I think that dichotomy is so interesting to explore. It’s those things that made people feel like she was their best friend, because she was this brutally honest writer who could point out your flaws even though she wasn’t actually sitting next to you.

Reading the book, you’re confronted with the truth that most of Nora’s movies flopped in one way or another. After making a few hit rom-coms, other filmmakers would’ve rested on their laurels. Could Nora have done that and had a very different career, or would that have been totally antithetical to her as a person?

She didn’t want to be pigeonholed, and she really liked challenging herself, even though she acknowledged in her writing too that she had flops. If you look at something like Silkwood or Mixed Nuts, there’s romance in it, but it’s not a rom-com. It was great that she was constantly pushing her own boundaries. She really wanted to make dark comedy work, especially with Lucky Numbers, which is a rough watch if you’ve ever seen it. Lisa Kudrow is the best part of that movie, but the movie’s so confusing to me.

I always feel like we talk about her rom-com trio: You’ve Got Mail, Sleepless in Seattle, and When Harry Met Sally. I know those are the most famous, but I always say Heartburn is an honorary fourth to me, even though it’s a breakup rom-com. I also feel like Michael is a rom-com, even though it’s not considered as such, but it’s such a sweet movie and has that main crux to it.

You admit that some of these movies are a rough watch, but write about them all with warmth. How did you acknowledge the misfires while still being respectful to your subject?

Lucky Numbers was one where I was personally struggling with. But I feel even within some of the movies that weren’t as critically acclaimed or as cohesive, there were still elements that showed how brilliant Nora was—whether that was through the dialogue, her character development. Even if the plot was suffering, there were still elements that made the films Nora, and helped show how she grew as a writer-director. Everyone tries and fails to move out of their comfort zone at some point and it’s pretty admirable she did it.

Strangely enough, it seems that whenever Nora got more obviously autobiographical like This Is My Life or Hanging Up, some people bristled. Do you have the sense that those flops hit differently for her?

Hanging Up was tough…I feel like there were elements of her and her sisters throughout all of that, because her sister wrote the book. But Diane Keaton ended up stepping in to direct it. There’s not a ton of information available on whether or not there was a falling out between anybody, but it was very clear that the content was quite close to [Nora]— maybe too close for comfort. So getting someone else to direct was maybe a move to protect herself and her relationship with their family.

This Is My Life, even at the time it felt like a film that she would be defined by. It’s not her most famous film, but it’s a beautiful film. It’s so interesting that that is the movie that made Lena Dunham want to make movies. Julie Kavner is incredible in it. The exploration of the mother-daughter bond in that movie is just so incredible and true to life. And I don’t know if she necessarily saw it as a flop, because it was a really great movie.

Is there a Nora Ephron film that is most due for rediscovery?

I feel like it’s a tie. Silkwood, I’ve talked to some people and they didn’t realize she was involved in it. That was a groundbreaking role for Cher; Meryl’s amazing in it. I’m very particular about biopics, but I really loved that one. And I want to say Bewitched because, while I don’t think that Will Ferrell was the best casting—and I love him—I do think that it was super meta and ahead of its time. Nicole Kidman is just so charming in it. With time, opinions change. That movie even has a cult following now.

Just as Nora loved to reference other movies in her films, you make the case that a lot of modern rom-coms wouldn’t exist without Nora. Was there a recent project with ties to Nora that most amused you?

I love drawing the connections of epistolary storytelling between Nora’s work and To All the Boys I’ve Loved Before or P.S. I Love You. Sleeping With Other People, that’s a fun one. At the time I wasn’t thinking about it, but re-watching that I was like, ‘Oh, wow, this is like When Harry Met Sally—but lots of sex.’” Jennifer Kaytin Robinson, who I interviewed for the book, Nora is a huge inspiration for her. Someone Great is obviously an amazing breakup rom-com. To me, that was like her Heartburn—less scathing, of course. I see a lot of parallels with [Robinson] and Nora because she’s trying to push the genre forward in a way that I don’t think we’ve seen with a lot of writer-directors.

As you recounted Nora’s influence on a lot of modern films, I couldn’t help but wonder what she would think of recent things that have happened within her thematic purview, like the concept of Girl Dinner or the reality show Love Is Blind.

My mind did go to, “Would Nora be on social media now?” I feel like she would publicly hate social media, but secretly have a burner account, like Lorde’s Onion Ring account. She would have some weird thing. Or she’d pull a Susan Orlean and start drunk-tweeting one night for the first time in 20 years. It would go viral, be the thing we talk about for years. Love Is Blind would be a guilty pleasure for her. I don’t know if she’d admit how much she loves it. How she would publicly portray the way that she feels about certain things would be totally different than how she privately enjoys them.

You have said that, like Julia Child’s reaction to Julie Powell in Julie & Julia, you don’t think Nora would’ve liked your book publicly, but maybe she would have secretly kept a copy. As you point out, we often forget that this person we associate with fall and coziness was a far more prickly and complicated person in reality.

As much as she made great work, she could be tough on sets. I didn’t know her personally, but I do think part of that was maybe a protective layer too. Because there were so few female directors during that time. She wanted this career for herself, and she felt like she had to compete with the boys club. There are a lot of women in Hollywood that get reputations for behaving a certain way, when maybe they’re actually not being all that tough, they’re just trying to survive. So it’s a nuanced conversation. People would say that even though she could be tough, they also saw how wonderful she could be, how much of a mentor, the lunches or dinner parties she would throw. She was just a complex person.

You interviewed some of Nora’s friends and collaborators for the book. What stuck with you from those conversations, and was there a dream interview that you couldn’t secure?

There are a few things that stuck with me. One is that Julia Roberts could have played Cookie, which would’ve been interesting. Heather Burns, I knew that she was cast in a couple of Nora movies [You’ve Got Mail, Bewitched], but she was her mentee, which I didn’t really know. She told this story about how she found out that Nora died when she was at dinner. She was so upset, but realized, “Nora would literally yell at me and tell me not to be upset and eat my food, because I would be wasting it.” And I just thought that was really sweet. Hearing friendship stories from [Sleepless in Seattle executive producer] Lynda Obst, Andie McDowell recounting the pie song [from Michael].

In terms of who I wanted to talk to, I tried to talk to everyone you could think of. I almost got Cher, which was like, “Please just let me get to Cher.” [Her team was] like, “We’ll try to make it happen after the holidays.” After a year and a half of me trying, it didn’t happen. I really wanted Meg [Ryan], but it did not happen.

In some alternate timeline, if you had the chance to have a meal with Nora, what would you ask her and what would you be eating?

That’s such a good question. I would ask her if she secretly wishes Mandy Patinkin had played the Carl Bernstein character in Heartburn—if she thinks it would’ve been a better movie. [Jack Nicholson eventually played the role inspired by Ephron’s second husband, after Patinkin was fired and Kevin Kline declined to replace him.] Because I know Meryl wanted Mandy—and I just love Mandy. And we would be eating her meatloaf with a side of key lime pie.

This interview has been edited and condensed for clarity.