‘When Harry Met Sally’ succeeded after Rob met Nora, Billy, and Meg

Meg Ryan and Billy Crystal helped redefine the modern rom-com in 1989’s “When Harry Met Sally …” (Columbia Pictures/MovieStillsDB.com)

Ultimate Movie Year finds the best films from weekends past to build an all-star lineup of cinema.

"When Harry Met Sally ..."
Released July 12, 1989
Directed by Rob Reiner
Where to Watch

It takes a remarkable confluence of talent and circumstance to not only make a great movie, but also one that is remembered throughout the ages. "When Harry Met Sally …" was a notable hit in the summer of 1989, but its endurance and legacy over the other romantic comedies of its era stem from a director in the midst of one of the all-time great runs, a recognizable comedy star entering the apex of his career, and the emergence of two women who would launch powerful and influential careers equal to their male counterparts.

The movie follows the journey of its title characters, Harry (Billy Crystal) and Sally (Meg Ryan). They meet as college graduates sharing an awkward ride from Chicago to New York, and then finally reconnecting a decade later to begin a friendship. The new friendship forces Harry and Sally to overcome their negative first impressions of each other while using the opportunity to understand the opposite sex better because they are not in a romantic relationship … until they are. Can they retain there past connection to each other?

Born to actress Estelle Reiner and comedy writer Carl Reiner, Rob Reiner entered show business as an actor, notably as a regular on TV's "All in the Family." In the 80s, he became a director, starting with 1984's "This is Spinal Tap." Over the next few years, Reiner would distinguish himself as a director by switching genres and making one of the best films in that particular genre. The mockumentary "This is Spinal Tap" is still regarded as one of the funniest movies ever. Still, Reiner also was behind the coming-of-age drama "Stand By Me" in 1986, the fairy tale fantasy "The Princess Bride" in 1987, and later, the Stephen King horror adaptation "Misery" in 1990, and the courtroom drama "A Few Good Men" in 1992. Both aspiring and veteran filmmakers would be thrilled to make a movie as good as any one of these in their careers.

By the time Reiner decided to tackle the romantic comedy genre, he was reentering the dating world after coming out of a divorce from Penny Marshall, as one does. He connected with Nora Ephron, a journalist and screenwriter who spun her own divorce into the novel "Heartburn," which she eventually adapted into a 1986 movie.  After a lunch conversation, Reiner and Ephron decided to combine their observations about dating with a great hook, "Can a man and woman sleep together and remain friends?"

"I had known a couple of guys who I went out with in college and just hated," Ephron said in the behind-the-scenes documentary, "How Harry Met Sally …" "I saw them again and just hated them. At that point, if you've seen enough movies, you kind of know that you're destined to be together because you hate them so much. I thought I could have some fun with that idea, of two people just keep brushing up against one another and just think the other one is impossible."

What transforms "When Harry Met Sally …" over so many other romantic comedies is that the collaboration between Reiner and Ephron was a partnership, each bringing their perspectives to the table to balance the gender dynamics. For the male lead role, Reiner brought in his friend Crystal, whose career in comedy continued to climb throughout the 80s. That collaborative spirit behind the film continued, as Crystal punched up the humor as Harry. The final piece of the puzzle was Ryan, then a young actress known for mostly supporting roles, as Sally. Diane Keaton's performance as the title character in 1977's "Annie Hall" was somewhat of an inspiration for Sally as far as fashion and adorable neurotic quirks. Still, Ryan brought her own energy to the role of a woman whose doe-eyes belie confidence and experience.

The filmmakers scored on another winning decision by casting Carrie Fisher and Bruno Kirby as Harry and Sally's best friends who end up falling for each other. The conversations between Harry and Kirby's Jess were inspired by Reiner and Crystal's real-life friendship. Meanwhile, Fisher's Marie must be a first-ballot hall of famer in the "Best Friend in a Romantic Comedy" wing because she crushes and wins almost every scene she's in, like Mariano Rivera throwing closeout pitches for the New York Yankees.

"When Harry Met Sally …" is heavily inspired by the films of Woody Allen, such as the location of New York City, the jazz soundtrack (here composed by Harry Connick Jr.), and even the font design of the credits. And yet, it is as good, if not better, than any of Allen's work, and that's because of the strong collaborative spirit between Reiner, Ephron, Crystal, and Ryan. For a movie that markets itself as the journey of the relationship between a man and woman, you really can see an authentic voice and balance between the genders on screen. Harry and Sally feel honest, real, and genuine. That's because of the behind-the-scenes representation that came from Reiner and Ephron, instead of having a male develop a female character and vice-versa. 

"When Harry Met Sally …" faced stiff competition at the box office, as the summer of 1989 saw several sequels to popular franchises and the monster debut of Tim Burton's "Batman." "When Harry Met Sally …" opened in a handful of theaters in Week 28, and then, it expanded in the following weeks and would become a surprise success of the crowded summer with $92 million domestic gross. The movie received only one Academy Award nomination, a Best Original Screenplay nod for Ephron. Like another 1989 film, "Do the Right Thing," "When Harry Met Sally …" would continue to cement its place in the hearts of movie lovers everywhere. Countless cable viewings and video store rentals kept the film fresh in our minds, and while the success of "When Harry Met Sally …" revived the romantic comedy genre and spawned many imitators, few, if any, were able to match its heights. 

"Harry and Sally may be a match made in hell, but watching them is movie heaven," Peter Travers wrote in Rolling Stone. "Reiner's fifth feature … is a ravishing, romantic lark brimming over with style, intelligence, and flashing wit."

You also can't underestimate the impact the movie had for its filmmakers and cast. Reiner would go on to make several more stone-cold classics, and while his batting average has fallen in recent years, you can put up his first decade of films against any other directors. Crystal's career and popularity grew, even more, leading to starring roles in hits like "City Slickers," chances to direct his own films, and most notably, a longtime host of the Academy Awards. Ephron received Oscar nominations for her first two films and turned the success of "When Harry Met Sally …" into her own distinguished directorial career. Finally, Ryan's breakout performance created a new marketable star in Hollywood, and she would continue to work with Ephron on movies like 1992's "Sleepless in Seattle," and 1998's "You Got Mail."

"When Harry Met Sally …" remains one of the funniest and best romantic comedy films of all time. Its heart lies in the collaborative spirit of Reiner and the representative talents of Ephron, Crystal, and Ryan to elevate the director's already considerable abilities. It's witty, smart, moving, and heartwarming, like the classic movie romances Ephron is so fond of, and we're all lucky to have what they're having.

The Weekend: Falling in-between Independence Day weekend and the mid-July sweet spot that usually sees the last of the summer's significant blockbusters released, Week 28 is an excellent spot to catch some sleeper hits of the season, like "When Harry Met Sally …"

"Easy Rider," a classic and influential movie in film history, made its debut in theaters this weekend in 1969. Directed by, written by, and starring Dennis Hopper (who co-starred with Peter Fonda), the movie documents the trip (road and otherwise) of two motorcycle-riding hippies across America. "Easy Rider" helped bring the underground cinema to the mainstream, and was crucial in the development of the New Hollywood of the 70s.

In addition to the release of "When Harry Met Sally …," there are several other movies that use the unique elements of New York City to make the location another character. Kurt Russell broke into a dystopian version of the city in the 1981 John Carpenter classic, "Escape from New York." The Muppets completed their original trilogy of films while marrying off Kermit and Piggy at the height of their popularity in 1983's "The Muppets Take Manhattan." That same weekend in 1983 also saw John Travolta return in the sequel to "Saturday Night Fever," "Staying Alive," which was directed by (checks notes) … Sylvester Stallone? Speaking of unexpected filmmakers, Bill Murray made his directorial debut in 1990, starring as a bank robber unable to leave town in the very underrated, "Quick Change." Still, it had the misfortune of opening against "Ghost," the haunting romantic film with Patrick Swayze, Demi Moore, and Whoopi Goldberg that became the biggest hit of the year.

It's also an excellent weekend for science fiction movies. The beginnings of the video game revolution and computer-generated effects helped set the stage for 1982's "Tron," which features Jeff Bridges entering the digital world. Director Robert Zemeckis, whom we discussed last week with "Back to the Future," looked up to the stars in his film, "Contact," from 1997. 2000's "X-Men" boosted Marvel superheroes' profiles in film, a success that would go on to change the industry. The Planet of the Apes series returned to respectability in the mid-10s, thanks in part to director Matt Reeves' "Dawn of the Planet of the Apes" in 2014 and "War of the Planet of the Apes" in 2017.

Two young Black filmmakers released their debut features on Week 28, dealing with the trauma of violence in their communities. John Singleton's "Boyz n the Hood" from 1992 is a drama about the struggles of Black teens growing up in gang-filled streets of South Central Los Angeles. Ryan Coogler dramatized a true-life story about Oscar Grant, an unarmed Black man killed by police in Oakland, in 2013's "Fruitvale Station." Both are going out of your way to see.

It's pretty crazy that two of our best American action directors, James Cameron and Kathryn Bigelow, were married once upon a time. After their short-lived relationship ended in a divorce, they individually produced two notable films in the 90s. Bigelow directed Patrick Swayze and Keanu Reeves in the surf-boards-and-bank-heists flick from 1992, "Point Break." Meanwhile, Cameron collaborated with one of his biggest stars, Arnold Schwarzenegger, for the last time in 1994's "True Lies." 

By the time the 00s rolled around, Reese Witherspoon had taken over Meg Ryan's spot as Hollywood's leading blonde comic actress with roles in "Legally Blonde," released in 2001. But for the most part, movie comedy during that decade was ruled by the so-called frat pack. Will Ferrell fully unleashed his comic persona, along with several funny supporting men who would break out on their own, in 2004's "Anchorman: The Legend of Ron Burgundy." Vince Vaughn, who has a small role in "Anchorman," got his mojo back while teaming with Owen Wilson in 2005's "Wedding Crashers."

For a time, the biggest movie franchise in the world was Harry Potter, and several films in the series were released here. "Harry Potter and the Order of the Phoenix" debuted in 2007, and the eagerly anticipated finale, "Harry Potter and the Deathly Hallows - Part 2" premiered in 2011. The Harry Potter series (and subsequent fandom) would end up being referenced in Richard Linklater's "Boyhood," the 2014 fictional film the director spent 13 years making.

The Illumination animation studio has made a profitable business producing family films that are not the worst of the genre, but you could also definitely do better. Nonetheless, the studio launched several of its biggest hits in July, including 2010's "Despicable Me," 2015's spinoff "Minions," and 2016's "The Secret Life of Pets." 

Other notable movies released on this weekend include 1989's "License to Kill," 1993's "In the Line of Fire," 1998's "Pi, 1999's "American Pie," 2001's "Made," 2003's "Pirates of the Caribbean: Curse of the Black Pearl," 2005's "Charlie and the Chocolate Factory," and 2009's "Bruno."

Next Week: "Aliens"

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