Joyelle Ronan
When Sydney Sweeney began promoting her new romantic comedy, Anyone But You (2023), she proclaimed on The Kelly Clarkson Show that, “We’re making the rom-com big again.” The idea of a romantic comedy renaissance might evoke screwball films of the ’30s and ’40s, Barbara Stanwyck tripping Henry Fonda in The Lady Eve. Or Audrey Hepburn and Gregory Peck Vespa-ing through Italy in 1953’s Roman Holiday. Maybe it’s the diner scene in When Harry Met Sally (1989), after all, the ’80s to early ’00s is when romantic comedies were really in their prime. But, even in the genre’s golden age, the ’90s really stand out as a decade when rom-coms flourished in both frequency and quality.
The year 1990 started off strong with Pretty Woman, yet it wasn’t until the latter half of the decade that rom-coms started to be released more frequently. While Nora Ephron may have penned her last Tom Hanks and/or Meg Ryan romance in 1998 and Shakespeare in Love took home the Oscar for Best Picture, the genre had yet to see one of its best years. While 1999 is often regarded as one of the best years in the history of film, the same rings true of rom-coms. During that year, at least one romantic comedy was released nearly every month—a total of around 15, depending on how strictly a rom-com is defined.
Examining the state of romantic comedies 25 years ago will give insight into why Sweeney and others are hoping for a renaissance of the genre. Besides the sheer amount of films, what made 1999 a good year for rom-coms?
She’s All That
In his 2019 book Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen, author Brian Raftery details the seedy reality of the high school fairy tale She’s All That. While it might have been a power move by the Weinstein brothers to prove their company Miramax could compete with bigger studios, what may have been a cash grab is now a teen classic. Unlike many of its rom-com predecessors, She’s All That didn’t have a cast of big name celebrities. While Freddie Prinze Jr., who plays a popular soccer star named Zack Siler, already had I Know What You Did Last Summer under his belt, it was Rachel Leigh Cook’s first starring role. That doesn’t mean that the movie didn’t have talent, it featured up and coming actors and performers like Usher, Kieran Culkin, and Anna Paquin. Loosely based on the 1913 play Pygmalion, which has inspired other films including My Fair Lady (1964,) Cook’s character Laney is an art nerd who becomes the object of Zack’s affections when he’s challenged to turn her into the prom queen. Even though critics gave the film mixed reviews, it reached Number One at the box office in the first week of its release.
Even if a person has never actually seen the movie, they are likely familiar with the troupe of “girl takes off her glasses and guy suddenly realizes she’s hot.” But, without seeing She’s All That, they wouldn’t know that Laney actually mocks Zack when he tells her she should wear contacts because she has beautiful eyes. Her big makeover should have been anticlimactic; she got a haircut and contacts. But, the way the scene is shot is what made it so effective. Laney descends from the staircase in her red dress and the way Zack looks at her is the way everyone wants someone to look at them. The audience has watched him fall for her slowly, but in that moment, it’s finally clicked. It’s not really about Laney’s change of appearance, it’s about Zack’s change of character. He’s in love and Kiss Me by Sixpence None the Richer plays. Then she trips and he catches her fall, because after all it’s a romantic comedy.
Because the genre is heavily built on predictably, a romantic comedy needs to have memorable imagery to make it stand out. They are built on short impactful scenes that make the audience feel something. An action movie needs explosions and stunts, but a rom-com just needs two people bumping into each other on the street or a prolonged moment of eye contact while the perfect song plays. There are plenty of interesting and funny scenes in the film, basically anytime Matthew Lillard, who plays a reality television loser, is on screen. But it’s the simplicity of the staircase scene that makes it perfect. A call for more “big” rom-coms is really asking for small moments that are executed to perfection.
10 Things I Hate About You
If She’s All That was the prototype for the ’90s version of a John Hughes teen movie, then 10 Things I Hate About You was the superior final product. They have a lot in common—both are based on classic literature (Taming of the Shrew in the case of 10 Things), have iconic soundtracks, and end with a prom. But where She’s All That found success in a pared-down plot, 10 Things benefits from following the complicated comedy of its Shakespearian source material. When sweet and slightly nerdy Cameron (Joseph Gordon-Levitt) starts Padua High, he is immediately entranced by popular Biana (Larisa Oleynik). The problem is that Bianca isn’t allowed to date until her sister Kat (Julia Stiles) does. Surly feminist Kat has no desire to date so Cameron and his friend Michael (David Krumholtz) hatch a plan to set up Kat with the mysterious and scary Patrick (Heath Ledger) while tricking Joey (Andrew Keegan), the object of Bianca’s affections, into funding the scheme.
Screenwriters Karen McCullah and Kirsten Smith managed to fit a lot of story into only an hour and 37 minutes. The duo has a knack for writing romance, together they wrote Legally Blonde (2001), Ella Enchanted (2004) and another Shakespeare adaption, this time Twelfth Night, She’s the Man (2006). As a high school student, McCullah titled a diary entry about her boyfriend “10 Things I Hate About Anthony” which served as inspiration for the name and Kat’s ending speech, concluding with “I hate it that you’re not around. And the fact that you didn’t call. But mostly I hate the way I don’t hate you, not even close, not even a little bit, not even at all.” The movie even weaves in some dialogue from Taming of the Shrew as an homage to its source material, Cameron says to Michael “I burn, I pine. I perish,” regarding his feelings towards Bianca. While McCullah and Smith successfully wrote two endearing love stories within the film, they also nailed the comedy, which is equally as important.
When thinking about what separates a bad rom-com from a good one or even a good one from a great one, it’s easy to focus too much on the romance and forget to make it funny. There are so many different styles of humor, this slightly raunchy teen comedy approach would fail horribly in a movie like You’ve Got Mail. But it really works in this context: the story feels balanced. The humor is quick-witted and perfectly delivered by the cast. In comparison to the current romantic comedies being churned out by Netflix and Hallmark, 10 Things I Hate About You feels refreshing despite being 25 years old. In his review of the film, Roger Ebert said, “The movie almost but not quite achieves liftoff against the gravitational pull of the tired story formula.” But, the formula isn’t the problem. People watch romantic comedies with the expectation of meet-cutes, clichés and true love. Just because the genre follows a formula, doesn’t excuse it from a poorly-written, unfunny dialogue and characters. The scene of Heath Ledger running across the bleachers singing “Can’t Take My Eyes Off Of You” while being chased by security guards will never fail to make me laugh.
Never Been Kissed
Of every character Drew Barrymore has played, Josie Geller in Never Been Kissed might be her most memorable—Barrymore even resurrected the awkward teen known as “Josie Grossie” for a segment on The Drew Barrymore Show. But whereas She’s All That and 10 Things I Hate About You were about teenage romances, Josie is actually a 25-year-old journalist undercover as a 17-year-old in order to find a story. Josie was unpopular and ruthlessly bullied during her actual high school years and now has a chance to rewrite her past. Her love interest is her English teacher, Sam Coulson, played by Michael Vartan, who struggles with his feelings for Josie, believing her to be a high school student.
Never Been Kissed is an important case study in understanding why rom-coms remain so beloved. Cinema has the ability to allow the audience to relate to their own life and explore fantasies and a life they can never have and Never Been Kissed accomplishes both. Love is something humans instinctively seek and romantic love can be a struggle to find, therefore romantic comedies can uniquely provide comfort to audiences by watching others fall in love in a lighthearted way that other genres cannot. They are both relatable—Josie desires a romantic connection where she can be herself, and not relatable—the circumstances in which she finds love. Still, however fantastical they may be, rom-coms need to provide a certain level of hope and belief in love. In 2023, Allora Campbell went viral after sharing her real life never-been-kissed story. The 32-year-old was interviewed by Barrymore and shared that like Josie, she’s always dreamed of a fairytale romance and didn’t receive her first kiss until her current age.
“We all have a little Josie Grosie in all of us,” Barrymore said on her talk show in response to a fan question asking why she wanted to play the role of Josie. “We all feel awkward. We all want to fit in. We admire a group of people and wonder if we can see ourselves in it or if they’ll let us in. We put so much value in those other people. And along life, you learn that you have to accept yourself and you’ll find your pod.” In 1999, a time when the lines of popular and nerd were blurring, this was an important message that is still relevant and relatable today.
Notting Hill
At this point, it may seem like all romantic comedies in 1999 were made to appeal to teens. But, not only was Notting Hill targeted towards a more mature audience, it’s one of the rare rom-coms to get award buzz. At the 57th Golden Globes Awards, the film was nominated for Best Motion Picture–Comedy/Musical, Best Motion Picture Actor–Comedy/Musical for Hugh Grant, and Best Motion Picture Actress–Comedy/Musical for Julia Roberts. While it didn’t take home any awards, Notting Hill became the highest-grossing British film of all time and is regarded by many as one of the best romantic comedies of all time. Roberts plays Anna Scott, a famous actress who wonders into a bookshop owned by William Thacker, played by Grant. Featuring not one, but two meet-cutes, they later bump into each other causing William to spill his juice on Anna.
The film takes place over a longer period of time than most romantic comedies where falling in love happens fast. To allude to more literature, they’re star-crossed lovers threatened by fame which complicates the conflict beyond the lying and seeking forgiveness seen in the previous films discussed. Also, She’s All That, 10 Things I Hate About You, and Never Been Kissed featured, at the time, mostly unknown or up-and-coming actors, Notting Hill brings star power. While A-list celebrities aren’t required to make good rom-coms, good actors are. The actors not only have to nail the subtleties of falling in love and have the comedic chops, they also need to believe in the very concept of a rom-com. Roberts told the New York Times, “This is a genre that I love to participate in and watch, and I think they are hard to get right. There is a really simple math to it, but how do you make it special? How do you keep people interested when you can kind of predict what is coming?”
For years actors who previously stared in romantic comedies have been denouncing them. Kate Hudson recently spoke out about the difficulty of getting male movies star to want to star in rom-coms. It’s not only a problem to get the stars, but to get them to commit. In 2023, rom-com veterans Reese Witherspoon and Ashton Kutcher starred in Your Place or Mine. It should have been an instant hit, but was a huge disappointment. The pair had zero chemistry which could be surmised by their red carpet photos without ever needing to see the film. Chemistry can’t be faked in a rom-com, and Hugh and Roberts delivered earnest chemistry. Roberts, especially, when delivering her now iconic line, “I’m just a girl, standing in front of a boy, asking him to love her.”
There are many more rom-coms from ’99 including another Roberts-led, albeit less successful, film, Runaway Bride. There’s also Blast From the Past, Simply Irresistible, Drive Me Crazy, and Mansfield Park. While certain elements and scenes from these films have aged poorly, the universal messages remain true. Judging from these four films, rom-coms require memorable moments, strong scripts that balance both romance and comedy, a foot in reality and fantasy, and authentic performances. That’s a tall order and likely the reason why the genre slowly started to disappear. Given the success of Anyone But You (unsurprisingly loosely adapted from Much Ado About Nothing,) there’s hope that “big” romantic comedies can make a comeback in 2024.
