Few names in the romantic comedy genre loom as large as writer/director Nora Ephron. Her trilogy of Meg Ryan hits, When Harry Met Sally… (1989), Sleepless In Seattle (1993) and You’ve Got Mail (1998), sit mightily atop the genre canon, but her talents and influence go much deeper than these classics. The romance of the films is tinged with a darkness and cynicism that carries over from the wry, caustic writing she did for years as a reporter, essayist and novelist. Indeed, her unique voice comes from an inherent contradiction - that between the fairytale, Hollywood romances she grew up loving, and the world-weary edginess of the hard-drinking Jewish screenwriters who raised her.

Ephron was born in New York City, a location that would become an indelible character in many of her films, but her parents, the playwright and screenwriting team of Henry and Phoebe Ephron, soon whisked her and her three sisters off to Beverly Hills. There, they wrote such comedy classics as the Spencer Tracy / Katharine Hepburn vehicle Desk Set, but after much success, their screwball comic stylings went out of fashion in the counterculture 60s. Phoebe slowly succumbed to drinking and died at 57 from cirrhosis of the liver, but not before she achieved her life’s mission: to make sure that all four of her daughters became writers. 

Though Nora Ephron had many great mentors across a long career, the first and most important was her mother. And chief among Phoebe’s pearls of wisdom were: “everything is copy” and “write it funny.” Over a career that spanned countless articles and upward of a dozen films, with the highest of highs and many rocky lows, Nora Ephron distinguished herself by hitting that narrowest of targets over and over again - pulling out truths from the rawest and most painful parts of her own experience, and making sure to deliver them with a cutting sense of humor that was all her own. 

Much can be learned by taking a journey through the career of the great Nora Ephron. 

Meryl Streep in 'Silkwood'

1. Nichols Film School: Silkwood (1983)

Ephron rose to fame by breaking glass ceilings in the journalism world and writing biting essays and cultural critiques. She garnered further attention when she married famed Watergate journalist Carl Bernstein. Her first dalliance into screenwriting came when she collaborated with Bernstein on a rewrite of William Goldman’s script for All The President’s Men, itself based on Bernstein’s book that he wrote with Bob Woodward. Goldman hated the changes, and only one of Ephron’s scenes made it into the final film, but she continued to write unproduced screenplays and even got one made into a 1978 TV movie, Perfect Gentleman.

Ephron’s film career might’ve felt like it was over before it began until Meryl Streep, hot off a star-making Academy Award win for Kramer Vs Kramer (1979) asked for a meeting. Streep had attached herself to a movie based on Karen Silkwood, a whistleblower and union activist who suffered from radiation poisoning while working at a chemical plant in Oklahoma in the early 70s, and then mysteriously died in a car accident on her way to a testimonial interview with a New York Times reporter. Streep thought Ephron’s cutting journalistic voice could be right for the project, but Ephron wasn’t convinced that the tragic story fit her sensibility until she heard an anecdote about Silkwood mischievously flashing a co-worker, and suddenly, she knew this was someone she wanted to write about. Ephron enlisted fellow reporter and culture writer Alice Arlen, who had researched the real case, to co-write the script with her.

Director Mike Nichols signed on to direct the film, and was so collaborative with his writers on location in New Mexico and Texas that Ephron deemed her experience the Nichols Film School. The ever generous Nichols answered any questions Ephron had about the directorial process, and always advised her to ask, “What is this story about? What is this scene about? What is this section of the movie about?” Through Nichols’ mentorship, Ephron honed her skills as a storyteller and began her journey toward directing films. 

Silkwood launched during the December awards season of 1983, and became a hit, garnering 5 Academy Award nominations including a first Original Screenplay nod for Nora Ephron and Alice Arlen. By fusing her experience in journalism with her mischievous “make it funny” mantra, and treating Mike Nichols as a storytelling mentor, Ephron was able to channel the humanity of the Karen Silkwood story perfectly, and establish herself in Hollywood. 

2. Everything is copy: Heartburn (1986)

After filing for divorce in 1980, having caught Bernstein in the midst of an affair, Ephron found that the only way to work through the pain was to resort to her mother’s old idiom: “everything is copy.” She wrote a thinly fictionalized account of the marriage and divorce called Heartburn, and though it received defensive criticism from the literary world, who thought it an attention-seeking hit piece, Ephron’s new pals, Mike Nichols and Meryl Streep, saw a film in it. Streep signed on to play the Ephron character, and in spite of Ephron’s objections, Nichols fired the original lead, Mandy Patinkin, after one day’s shooting, and cast Jack Nicholson as the Bernstein character. Ephron thought Jack’s abundant charms would make him too sympathetic to play the villain of the piece, but Nichols wanted to make a more balanced story about the dissolution of a marriage. 

When the film was released, Ephron got a hard lesson in the dangers of writing what you know. Critics savaged the film as a bitter bit of vengeance that was too close to home, a series of untethered recollections that didn’t cohere into a meaningful story because it was written by its central character. After translating someone else’s story to the screen so well with Silkwood and being showered with praise, Ephron was faced with her first critical disappointment by dramatizing her own experiences. Luckily for her, the failure wouldn’t last long. She’d struck up a friendship with another recently divorced filmmaker, Rob Reiner, and together, they were about to make cinema history. 

3. The art of collaboration: When Harry Met Sally… (1989)

Not long after Ephron’s divorce, Rob Reiner asked if she was interested in writing a courtroom drama for him. The answer was no, but the two struck up a rapport talking about their new dating lives. Ephron was horrified by how coarse and stupid single men could be about dating, and Reiner found humor in many aspects of Ephron, including the very particular way she would order a sandwich. Finally, Reiner came up with a movie pitch that Ephron found interesting: the question of whether a man and a woman could be friends without sex getting in the way. The idea provided a springboard off of which Ephron could bounce many of her observations and witticisms about modern life and dating that usually lived in her essays. A back and forth between the two quickly evolved into the iconic banter of Billy Crystal and Meg Ryan’s titular characters in When Harry Met Sally…

Reiner was from the more spontaneous, fast-moving world of sitcom television, and once they cast Crystal and Ryan, Ephron got a crash course in being less precious with her writing. Reiner loved involving every voice in the creative process, and taught Ephron that movie sets were like parties, and the director is the host, intent on creating the atmosphere and making sure everyone has a good time. So Crystal and Ryan began throwing in lines and pieces of their personalities as well, with Ephron fusing all of the ideas and personalities together into the tightest, funniest romantic comedy script of the modern era. And while Ephron and Reiner had originally intended for Harry and Sally to wind up apart in the end, proving that women and men can in fact be just friends, over the course of the creative process, Ephron married crime reporter Nicholas Pileggi, and Reiner fell in love with his wife-to-be, Michelle Singer. When it finally came time to shoot the finale, the lovestruck duo couldn’t help but give it a Hollywood ending. The result? One of the most influential films of the last 50 years. 

The movie became one of the biggest hits of 1989 and got Ephron another Academy Award Nomination for Best Original Screenplay. To this day, movie fans quote “I’ll have what she’s having,” and “When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible,” or this fan’s personal favorites, “Oh, but Baby Fish Mouth is sweeping the nation,” and “Six years later you find yourself singing ‘Surrey with a fringe on top’ in front of Ira!” Ephron had finally stumbled into creating one of the romantic comedy classics she grew up adoring. And she did it through the art of collaboration, through loosening her grip, kibitzing instead of writing, embracing the good and brushing off the bad, and then transcribing the spontaneous comic diamonds from the conversations. The banter between gal pals Meg Ryan and a fantastic Carrie Fisher crystalized Ephron’s sharp observational humor into its clearest on-screen form, and Hollywood took notice. 

4. Becoming a director: This Is My Life (1992)

In 1987, Dawn Steel became one of the first women to head a major studio as the president of Columbia Pictures, and oversaw the distribution of smash hit, When Harry Met Sally... Amidst the film’s success, Steel identified Ephron as a possible director. Ephron had just written My Blue Heaven (1990), a comic spinoff of her husband’s own mobster projects, true crime book, Wiseguy (1980), and its Martin Scorsese adaptation, Goodfellas (1990). Ephron’s script found a comic opportunity in Pileggi’s research and she created the story of a fictional mobster living in witness protection. But when director Herbert Ross proved unable to capture the comic flavor of Ephron’s vision, she realized that sometimes to get the job done right, you have to direct it yourself. 

Ephron’s old journalism friend turned producer, Lynda Obst, gave her Meg Wolitzer’s novel, This Is Your Life, about a stand-up comic who struggles to balance her career with her responsibilities as a single mother of two daughters. The resemblance to Ephron’s own upbringing was uncanny. Nevermind the fact that she planned to embark on her own brave new career path as a director while mothering two young kids. She set the film up with Steel at Columbia, and aptly retitled it, This Is My Life. Nervous about juggling her newfound responsibilities as director with her screenwriting duties, Ephron recruited an additional screenwriter, her trusted sister, Delia. Julie Kavner of Simpsons fame played the stand-up comic to hilarious, complicated effect, and Ephron’s friend, Carly Simon, who had worked on Heartburn, created a soundtrack of original music to accompany the lovingly photographed New York City setting. The Ephron sisters pulled from their own joys and pains as daughters of struggling creatives and “wrote it funny,” but the film failed to make a splash at the box office and received mixed reviews. 

Viewed now, it’s hard to believe that This Is My Life doesn’t have a better reputation. It’s a hilarious and moving New York story that would become Ephron’s trademark. Unlike with Heartburn, Ephron put her personal experiences into someone else’s story and got the balance just right. But despite the middling reception, Ephron had caught the directing bug and knew what she was doing now. Rather than turn back in the face of a perceived failure, Ephron did what she did best. She persevered and doubled down, charging ahead into her sophomore directorial effort, which would become a romantic comedy classic. 

Tom Hanks, Meg Ryan, and Ross Malinger in 'Sleepless in Seattle'

5. Blending real life and old Hollywood romance: Sleepless In Seattle (1983) 

With her directorial debut in the can and no money in the bank, Ephron was desperate for a job. Her directorial passion project was an adaptation she and Delia wrote of the French comedy play, Santa Claus Is A Stinker, about the employees of a suicide hotline on Christmas, but with a recent failure on her hands, no one would touch it. She threw her hat in the ring to write Adrian Lyne’s Indecent Proposal, regretting having passed up the opportunity to write Lyne’s smash hit Fatal Attraction on the grounds that it was misogynistic. The job would’ve put her kids through college and she later confessed she found the movie brilliant and hilarious with its male nightmare premise, but Lyne hired William Goldman for Indecent. 

Finally, she received the script of a romantic melodrama called Sleepless In Seattle, by unknown screenwriter Jeff Arch with rewrites by The Sting’s David S. Ward. The script, about a woman who falls in love with a widowed man by hearing him on the radio, was unfunny and very syrupy, but the An Affair To Remember ending on top of the Empire State Building resonated with Ephron. Her mother had taken her to a screening of the 1957 Leo McCarey film at a movie palace in Westwood as a kid and before young Nora could dry her eyes after the tearjerker ending, her mother introduced her to the film’s real life star, Cary Grant. So began a lifelong fascination with the delicate, blurry line between the stories on the movie screen and the realities of life. These are the themes she was intent on injecting into Sleepless by way of those two, golden Phoebe Ephron ingredients: pulling from lived experience, and making it funny.

The Ephron Sisters penned a romantic comedy rewrite of Sleepless that became a sensation around town, but caused the film’s director, Nick Castle, to leave the project. The producers invited Ephron to direct instead, and she cast her beloved Meg Ryan as the female lead, and hired the great Tom Hanks as the widowed man. She became more meticulous as a director this go round, recruiting Ingmar Bergman’s cinematographer, Sven Nykvist, demanding specifics of camera, lighting and production design, and even firing and recasting the actor who played Tom Hanks’ young son when his performance wasn’t cutting it. Her natural cynicism and the characters’ wry banter about the craziness of a premise in which the romantic leads don’t actually meet until the final scene, helped to undercut the tearjerker sentimentality. But regardless of the clever self-critique, when Ryan and Hanks finally meet atop the Empire State Building in a call back to Affair, it’s absolute, old Hollywood movie magic. Ephron couldn’t help but embrace the romance whole-heartedly.

Sleepless came out in the middle of summer as counterprogramming to shoot-em-up action movies like Cliffhanger and Last Action Hero, and became a smash hit. It wound up one of the highest grossing films of 1993, produced a top-selling soundtrack album, and got Ephron another Academy Award nomination for writing. Ephron had wanted to direct her cynical French farce, but in taking a romance rewrite job out of desperation, she wound up honing her truest gift - combining contemporary real life with the fairytale romance of old Hollywood. The results were undeniable. Ephron was now an A-list director, but in resorting back to her more cynical creative impulses, her career was about to hit some bumps. 

6. Returning to what you’re best at: You’ve Got Mail (1998)

The Ephron Sisters were able to get a green light for their Christmas suicide hotline movie, Mixed Nuts, after the success of Sleepless. And though it epitomized their sick, caustic senses of humor, with a miscast Steve Martin in the lead and a failure to properly translate the tone of the French original it was based on, the movie was critically panned and bombed at the box office. Luckily, they’d already signed on to rewrite Michael, a movie about an eccentric angel, to be played by John Travolta during a run of renewed popularity after Pulp Fiction. Ephron directed, and though the premise certainly has hints of the screwball comedies the Ephrons’ parents wrote, the finished film was tonally muddled and received mixed reviews from critics. 

Unable to match the acclaim of her earlier romantic comedies, Ephron jumped at a suggestion from Warner Brothers that she and Delia write a modern remake of Ernst Lubitsch’s A Shop Around The Corner (1940). The film told the story of two antagonistic coworkers who don’t know that they are each other’s anonymous romantic pen pals. Given the new prevalence of email culture, it was ripe for remaking, and Ephron reenlisted her Sleepless leads for the AOL-tinged, Upper West Side set, You’ve Got Mail. 

The film is maybe the perfect encapsulation of Ephron’s brilliance, pumped full of her pure love for her little Manhattan neighborhood, and classical Hollywood romcoms and reading, but undercut by a cynicism around corporate culture, and the death of independent business in the modern world. While in the end, independent bookshop owner Meg Ryan winds up with her secret e-mail penpal, corporate overlord Tom Hanks, in a tearful kiss in the park, he ultimately runs her little bookshop out of business. Ephron complicates the ending by acknowledging that though the leads get together, there’s no magical effort to save the indie bookstore. The cause is hopeless in this modern world, and the shop goes under. But the screwball mechanics, joke-a-minute screenplay and star chemistry somehow convince you that it’s a happy ending. It’s pure Ephron. 

In You’ve Got Mail, Ephron teaches us one of the best tricks in the book. If you ever find yourself in a creative rut, try to go back to what you love about movies. You’ve Got Mail is one of those films that has very little bearing on reality, or the hard-edged point of view Ephron often took on the world, but as a movie, it’s about as sumptuous as escapist entertainment gets, and only a true lover of cinema could have made it. It was as massive a hit as Sleepless, but as had become a pattern, Ephron would swerve away from what she did best to a few head-scratching failures before finding the perfect swan song a decade later. 

Meryl Streep in 'Julie & Julia'

7. Ending on a high note: Julie & Julia (2009)

Ephron began her film career with Meryl Streep, and 25 years later, ended it the same way. She’d had trouble in the 2000s, following the success of You’ve Got Mail. She helped Delia adapt her novel Hanging Up (1999) for Diane Keaton to direct and co-star in with Ephron muse Meg Ryan, but the film was panned. She acted as director-for-hire on another writer’s script, reteaming with Travolta and experimenting with action and thriller direction for dark comedy Lucky Numbers (2000). And finally, she and Delia adapted the sitcom Bewitched (2005) for Ephron to direct, but the Will Ferrell/Nicole Kidman starrer was what The New York Times called “an unmitigated disaster” and was nominated for five Razzie awards including worst director and screenplay. As ever, Ephron could only really thrive in Hollywood when presented with material she loved, and in what would be the final years of her life, producer Amy Robinson brought her just such a project. 

Robinson had conceived of combining the Julia Child autobiography My Life In France, and the Julie Powell book, Julie & Julia, based on Powell’s experience of starting a blog while attempting to cook every recipe in a Child cookbook in a year, into one film. A longtime lover of cooking, hosting and writing about food, Ephron found the project irresistible. It had everything, a story about marriage, about New York, about food, and a perfect role for her old friend, Meryl, which would gain her an Oscar nomination. For Julie, Ephron cast Amy Adams, who in recent starring turns in Enchanted and Sunshine Cleaning, was becoming an heir apparent to the Meg Ryan mold of America’s sweetheart. Ephron had even begun blogging as a contributor to the Huffington Post in recent years, so the titular blogger was a natural fit.

Ephron passed from cancer a few years later, in 2012, and in retrospect, Julie & Julia is a true gift of a final film. After a few years of uninspired work for hire that never seemed to find that perfect groove of Ephron’s earlier films, this project seemed to re-engage her and sum up so many of the things she loved to write about. The deliciousness of the food and French and New York settings and lush cinematography, are with a bit of the Ephron darkness in how the film addresses Child’s struggle to have children and Powell’s tragic example of fandom gone awry. Ephron was both the aspiring writer wanting so badly to be one of her heroes, and the aging hero that had no interest in said fan. It’s a movie as melancholy as it is delightful, delivered with that classic Ephron mixture of identifying the darkness in life, and making it funny. 

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To learn more about the great Nora Ephron, seek out Erin Carlson’s wonderful I’ll Have What She’s Having, and Kristen Marguerite Doidge’s Nora Ephron: A Biography. And of course, pick up one of the many wonderful essay collections, novels or memoirs written by Ephron herself.