From Hollywood with Love

The Rise and Fall (and Rise Again) of the Romantic Comedy

Scott Meslow

• Publisher: Dey Street Books
• Year: 2022
• Print ISBN: 9780063026292
• eBook ISBN: 9780063026315
• Topic: Media & Performing Arts
• Subtopic: Film & Video

An in-depth celebration of the romantic comedy’s modern golden era and its role in our culture, tracking the genre from its heyday in the ’80s and the ’90s, its unfortunate decline in the 2000s, and its explosive reemergence in the age of streaming, featuring exclusive interviews with the directors, writers, and stars of the iconic films that defined the genre.

No Hollywood genre has been more misunderstood—or more unfairly under-appreciated—than the romantic comedy. Funny, charming, and reliably crowd-pleasing, rom-coms were the essential backbone of the Hollywood landscape, launching the careers of many of Hollywood’s most talented actors and filmmakers, such as Julia Roberts and Matthew McConaughey, and providing many of the yet limited creative opportunities women had in Hollywood. But despite—or perhaps because of—all that, the rom-com has routinely been overlooked by the Academy Awards or snobbishly dismissed by critics. In From Hollywood with Love, culture writer and GQ contributor Scott Meslow seeks to right this wrong, celebrating and analyzing rom-coms with the appreciative, insightful critical lens they’ve always deserved.

Beginning with the golden era of the romantic comedy—spanning from the late ’80s to the mid-’00s with the breakthrough of films such as When Harry Met Sally—to the rise of streaming and the long-overdue push for diversity setting the course for films such as the groundbreaking, franchise-spawning Crazy Rich Asians, Meslow examines the evolution of the genre through its many iterations, from its establishment of new tropes, the Austen and Shakespeare rewrites, the many love triangles, and even the occasional brave decision to do away with the happily ever after.

Featuring original black-and-white sketches of iconic movie scenes and exclusive interviews with the actors and filmmakers behind our most beloved rom-coms, From Hollywood with Love constructs oral histories of our most celebrated romantic comedies, for an informed and entertaining look at Hollywood’s beloved yet most under-appreciated genre.

Chapter 1

When Harry Met Sally . . .

(And When Rob Met Nora and Changed the Course of Rom-Com History)

IF HISTORIANS HAD TO TRACE THE MODERN ROMANTIC COMEDY’S ORIGINS to a single time and place, they could hardly do better than the Russian Tea Room, on Fifty-Seventh Street in Manhattan, in the fall of 1984, when Nora Ephron and Rob Reiner sat down—as writers and directors have done for decades—for what would turn out to be one of the most remarkable lunches in Hollywood history.

Despite the chaperone-like presence of Reiner’s producing partner Andrew Scheinman—who had befriended Reiner in 1974 after he kicked his keys down a grate at a tennis club, which Reiner recalls as so cute it was “almost like a romantic comedy meeting”—this was essentially the professional equivalent of a blind date. Ephron, the daughter of two Hollywood screenwriters, and a successful magazine writer herself, was coming off a prolific prior year; in addition to the publication of her first novel, Heartburn, which was widely (and correctly) understood as a thinly fictionalized version of her breakup and divorce from Watergate journalist Carl Bernstein, she had cowritten the Oscar-nominated script for the biographical drama Silkwood, making her first big splash as a Hollywood screenwriter. Rob Reiner, the son of TV comedy legend Carl Reiner, had shot to fame in the 1970s playing Michael “Meathead” Stivic on the groundbreaking sitcom All in the Family, but had announced himself as a promising talent behind the lens with his 1984 debut feature, This Is Spinal Tap.

Though Ephron and Reiner had never met, it was easy to see why they might be drawn to each other. Both Ephron and Reiner were the children of successful Hollywood writers. Both Ephron and Reiner were recently divorced from well-known public figures: Ephron from Bernstein, and Reiner from Laverne & Shirley star Penny Marshall. Both Ephron and Reiner had achieved further fame by telling stories that self-consciously blurred the lines between reality and fiction. Why shouldn’t they sit down for a casual lunch and see if they might have anything they could work on together?

This meeting of the minds got off to a rocky start. “They told me an idea they had for a movie about a lawyer,” Ephron later recalled. “It didn’t interest me at all, and I couldn’t imagine why they’d thought of me in connection with it.”

Like any awkward date, Ephron had a choice to make: Should she smile and nod while counting the minutes until she could make a graceful exit? Or should she confess that she would never, ever work with these guys on this hypothetical lawyer movie? As was her habit, she decided to be honest and told them she wasn’t interested. And with no pressing business left to talk about, Ephron decided to fill the remaining time by drawing on the skills that had made her a remarkably successful journalist with a particular knack for writing profiles of cultural icons like menswear legend Bill Blass or Cosmo editor Helen Gurley Brown: by asking deep, probing, sometimes intensely personal questions. The subject quickly turned to the personal lives of Scheinman, a perennial bachelor, and the recently divorced Reiner. Ephron wanted to know: What is it actually like to be a single man? By which she meant, of course, What are single men really thinking?

Ephron’s unquenchable curiosity, her near-peerless ability to get to the heart of something, and her knack for repackaging those truths and sharing them with the widest possible audience was a skill set she had come by very honestly. Nora’s mother, Phoebe—a successful screenwriter alongside husband Henry, with romantic comedies like 1944’s Bride By Mistake and 1957’s Desk Set under their belts—had drilled into her children the immortal philosophy that “everything is copy.” She meant, more or less, that writers can and should use all of their life experiences—yes, all of them—as raw material for the stories they wanted to tell. Nora had taken this advice to heart. Heartburn was a “novel,” but its damning narrative was so close to the reality of her divorce from Carl Bernstein that he fought for script approval over the film adaptation Ephron was writing.

And while that lunch ended without Ephron agreeing to collaborate on Reiner’s idea for a lawyer movie, the conversation stirred something in all of them. A month later, the trio met again. Reiner had an idea: If the seemingly tiny but all-important differences between men and women were so stimulating to all three of them, why not write a movie about that?

Practically everything in When Harry Met Sally, which arrived in theaters five years later, sprang from Ephron’s ability to draw and then use the raw, messy material from other people’s lives. “She interviewed us like a journalist, got all these thoughts down, and that became the basis for Harry, and she became the basis for Sally,” recalls Reiner. The movie chronicles twelve years of an ever-evolving relationship between Harry Burns, a charmingly cynical chatterbox, and Sally Albright, a bright romantic optimist. (Ephron had originally imagined Harry Albright, a neurotic Gentile, meeting Sally Burns, an upbeat Jewish woman. But when Reiner revealed he intended to cast his then-girlfriend Elizabeth McGovern as Sally, Ephron concluded that McGovern couldn’t plausibly play a Jewish woman and swapped the characters’ last names.) After an early scene in which Harry and Sally debate whether or not men and women can be friends without sex getting in the way, they end up becoming close friends. When they finally have sex, many years later, their friendship is briefly ruined before they make up and get married—so I guess we’ll call that debate a draw.

Ephron, who called the writing sessions for When Harry Met Sally “as much fun as I’ve ever had,” fondly recalled how she and Reiner “fought bitterly” about everything, with her taking Sally’s side and Reiner taking Harry’s side in their debates about what men and women don’t understand about each other. Often, Ephron ended up working the substance of those debates directly into her script.

Ephron originally called the screenplay Scenes from a Friendship—an homage to Ingmar Bergman’s Scenes from a Marriage, which also zooms in on a relationship between a man and a woman. (It’s no coincidence that the most obvious precursor to When Harry Met Sally is Woody Allen’s Best Picture–winning Annie Hall, which New York Times critic Vincent Canby said was “essentially Woody’s Scenes from a Marriage.”)

By the time When Harry Met Sally was in preproduction, both Ephron and Reiner were confident in the strength of the script and the alchemical purity of its balance between the male and female perspectives. The challenge, they knew, would be finding the actors who could translate that balance to the big screen. Ephron, who once said that the movie itself has “no plot,” was aware that finding the perfect Harry and Sally would be just as important as, if not more important than, the writing. “Rob always said it’s the kind of movie that has a very high degree of difficulty in that it has no safety net,” she said. “It entirely depends on your caring about those two people.”

It Had to Be Him

For the music for When Harry Met Sally, Billy Crystal recommended Marc Shaiman, with whom he’d previously worked on Saturday Night Live. Reiner knew he wanted to score the movie with Great American Songbook standards, and Crystal was convinced that Shaiman was uniquely equipped to track down all the perfect deep cuts. “I, for some reason, do know every song ever written,” says Shaiman. “I went and met with Rob, and I went with my Rodgers and Hart songbook, because I was so sure that ‘I Could Write a Book’ was the most perfect song for the movie. The last line of it is, ‘Then the world discovers as my book ends how to make two lovers of friends.’

“It was Rob’s idea to use that song,” says Shaiman. “I don’t know whether I ever voiced it out loud to him—but I wondered if it was a good choice, because Diane Keaton sings that in Annie Hall, and there’s no question about the fact that When Harry Met Sally is a descendant of Woody Allen movies. But when Rob has an idea, he sticks with it.”

The soundtrack album for When Harry Met Sally was as much a hit as the movie itself, launching the career of an up-and-coming pianist named Harry Connick Jr. and sparking a national tour. But the album itself—which consists of Connick Jr.’s versions of classics like “Autumn in New York” and “Let’s Call the Whole Thing Off”—was indeed a Hail Mary effort when several labels refused to release the rights to the original recordings of the songs by performers like Ella Fitzgerald. Since a deal had already been struck with Columbia to release the When Harry Met Sally soundtrack, Shaiman and Connick Jr. were given what Shaiman calls “a little bit of money” to go off and record new versions with an orchestra. The resulting album went double-platinum.

For Reiner, one obvious answer for Harry came very close to home. Since 1975—when he was cast to play Reiner’s best friend on All in the Family—Billy Crystal had been Reiner’s actual best friend. The years had only brought them closer. As Crystal recalls it, they were “inseparable” following Reiner’s divorce from Penny Marshall, and he was in a unique position to understand just how much Harry was drawn from Reiner’s own life. Still, Reiner was reluctant to cast Crystal in the lead—in part because he valued their relationship so much. “Rob’s only concern was, ‘Am I going to ruin a really good friendship by having a friend play Harry?’ ” says casting director Jane Jenkins.

Reiner embarked on a lengthy search for Harry that included conversations with possible stars like Richard Dreyfuss, Michael Keaton, and a hot up-and-comer named Tom Hanks—and all while Crystal quietly waited in the wings, hoping for a call from Reiner, who had carefully avoided the subject with his friends. “I knew from agents and managers that he had met with almost every male actor my age, except me,” says Crystal. “I was not happy about that, but what could I do?” As Jenkins came to see it, it took all those false starts before Reiner had the perspective to see that Crystal was, indeed, the only actor who could play Harry exactly as Reiner saw him: a note-perfect cinematic riff on himself, as channeled through a friend who knew him better than anyone. “Rob finally said, ‘Why am I doing this? This is silly. Let’s go to Billy,’ ” says Jenkins.

At the same time, Reiner’s original plan to cast his girlfriend Elizabeth McGovern as Sally had fallen apart. When Reiner and McGovern broke up before When Harry Met Sally went into production—and Reiner concluded, apparently, that a man couldn’t maintain a professional relationship, let alone a friendship, with an ex—casting director Jane Jenkins and her partner Janet Hirshenson were tasked with finding another actress who could play Sally. Though names like Debra Winger and Molly Ringwald were kicked around, the production zeroed in on its star actress very quickly. “Meg was literally the second actress that came in,” recalls Jenkins. “She left the room, and Rob said, ‘It’s her part. Cancel everything else.’ ”

As it turns out, Reiner had been circling Meg Ryan to play the female lead in something for years. When Ryan was just eighteen, Jane Jenkins brought her in to read for the female lead in Reiner’s 1985 rom-com The Sure Thing. “Rob said, ‘She is actually terrific, this kid—but I don’t think she’s right,’ ” Jenkins recalls. “Two years later, we were doing The Princess Bride, and Meg came in. And Rob said, ‘I love this girl—but she’s not Buttercup. You know, if Bill Goldman had written that Buttercup should be the most adorable girl in the world, I would hire her right now. But I still think we could find the most beautiful girl in the world.’ ” As Reiner saw it, “the most adorable girl in the world” was exactly what he needed for Sally, whose quirks need to be so consistently endearing that by the climax of the movie, when Harry tells her that he loves that it takes her an hour and a half to order a sandwich, the audience nods along in agreement. Ryan, everyone agreed, was perfect. And in a Hollywood-worthy twist that had massive reverberations for the future of the entire rom-com genre, Ryan had to vacate her role in the dramedy Steel Magnolias to star in When Harry Met Sally. The role was recast with Mystic Pizza breakout Julia Roberts, who earned an Oscar nomination and a reputation as a rising star.

Finally, Reiner and Ephron—who was so present during production that Reiner referred to her, affectionately, as “another director”—had their Harry and Sally. Production began in August of 1988, and stretched through November (catching, a...

Table of contents

• Cover
• Title Page
• Dedication
• Contents
• Author’s Note
• Introduction
• Chapter 1: When Harry Met Sally . . .
• Essay: Meg Ryan: America’s Sweetheart (Until She Wasn’t)
• Chapter 2: Pretty Woman
• Essay: Sandra Bullock: Miss Congeniality
• Chapter 3: Four Weddings and A Funeral
• Essay Hugh Grant: The Hardest-Working Cad in Hollywood
• Chapter 4: Waiting to Exhale
• Essay: Bill Pullman, Patrick Dempsey, et al.: The Other Guys
• Chapter 5: My Best Friend’s Wedding
• Essay: Judy Greer: The Best Best Friend
• Chapter 6: There’s Something About Mary
• Essay: Adam Sandler: The Unlikely Leading Man
• Chapter 7: Bridget Jones’s Diary
• Essay: Drew Barrymore: The Self-Made Superstar
• Chapter 8: My Big Fat Greek Wedding
• Essay: Jennifer Lopez: The Triple Threat
• Chapter 9: How to Lose A Guy in 10 Days
• Essay: Reese Witherspoon: The Prodigy
• Chapter 10: Love Actually
• Essay: Will Smith: The Rom-Com Hero We Barely Got
• Chapter 11: Something’s Gotta Give
• Essay: John Cusack: The Reluctant Romantic
• Chapter 12: Knocked Up
• Essay: Katherine Heigl: The Apologist
• Chapter 13: Friends with Benefits
• Essay: Ryan Reynolds and Dane Cook: Two Roads Diverged
• Chapter 14: Untitled Royal Wedding Comedy
• Essay: Mindy Kaling: The Scholar
• Chapter 15: Crazy Rich Asians
• Essay: Henry Golding: New Star in Town
• Chapter 16: To All the Boys I’ve Loved Before
• Conclusion
• Acknowledgments
• Notes
• Copyright
• About the Publisher