With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

Rom-coms have happy endings. That fact is such a given that it’s often preemptively held against the genre. Why see a movie when you already know exactly how it’s going to end? It’s ironic, then, that one of the most beloved rom-coms of all time challenges the very nature of what we want from a happy ending. The all-around delightful My Best Friend’s Wedding—more so than maybe any other romantic comedy—benefits from not knowing exactly where things are going.

The 1997 film stars Julia Roberts as Julianne Potter, a commitment-phobic restaurant critic who’s sent into a tailspin when she learns her longtime best friend—and one-time college hookup, whom she made a pact to wed if neither were married by 28—Michael O’Neal (Dermot Mulroney) is about to marry the bubbly, 20-year-old White Sox heiress Kimmy Wallace (Cameron Diaz). So, while pretending to be a supportive maid of honor/honorary best man, Julianne schemes to stop the wedding—which, in classic rom-com fashion, is set to take place in just four days—and win Michael back. At one point, she briefly ropes her gay best friend and editor George Downes (Rupert Everett) into pretending to be her fiancé in order to make Michael jealous. But after her various machinations fail, Julianne eventually takes George’s advice and simply opens up to Michael about her feelings for him.

This is where My Best Friend’s Wedding breaks the rom-com mold: When Julianne confesses her love and impulsively kisses Michael, it doesn’t make him realize he’s in love with her. It only helps him confirm he’s actually in love with Kimmy. And even though she’s heartbroken, Julianne sets about righting her wrongs, ensuring the wedding goes off without a hitch.

There are plenty of meta rom-coms and rom-com parodies, but My Best Friend’s Wedding is something unique. It’s a deconstruction of the romantic comedy genre that’s also a fully functioning, agreeably mainstream version of one. On the one hand, the film unabashedly embraces rom-com tropes, like having an entire restaurant of people spontaneously join in a sing-along of Dionne Warwick’s “I Say A Little Prayer.” On the other, it raises questions about what would actually happen if someone were to engage in rom-com behavior in the real world. Julianne’s outrageous antics don’t land her her dream man. They almost uniformly backfire, threatening a whole lot of other people’s happiness in the process. Julianne is introduced as the heroine who’s nobly trying to win back the man she loves. But we slowly come to realize that she’s actually the villain in Michael and Kimmy’s love story—a fact Julianne has to grapple with as well.

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My Best Friend’s Wedding was such a cable TV mainstay when I was growing up, I more or less absorbed it through osmosis before I ever properly sat down and watched it. So I can’t authoritatively say how well the film’s ending plays as a “twist” on first viewing. That said, this “twist” isn’t explicitly presented as one: George encourages Julianne to tell Michael the truth, but he also warns her that Michael is going to pick Kimmy. Still, I have to imagine it was quite a surprise for audiences to watch Julia Roberts fail to get the guy in a Julia Roberts-led romantic comedy. Rom-coms are often accused of being static or formulaic, but by 1997 the genre was already critically examining its own tropes. And My Best Friend’s Wedding deftly shows how filmmakers can challenge genre conventions while still working within them.

Fairly early on, George also raises the question of whether Julianne is really in love with Michael, or if she’s just motivated by jealousy. And although Julianne claims her initial desire to “win” has since morphed into true love, just having the film pose that question creates a bit of emotional distance into the Julianne/Michael pairing. The film also implies that, despite their close friendship in college and into their early 20s, Julianne and Michael don’t really see each other much anymore. The rekindled spark between them is as much about wistfully trying to recapture their youth as it is a genuine romantic connection. Roberts and Mulroney have natural, sexy chemistry (there’s a shot of Michael sucking a ring off Julianne’s finger that, honestly, feels like it should’ve earned an R-rating), but their love never seems “meant to be.” So it’s not exactly a tragedy when they don’t wind up together.

In the rom-com subgenre about protagonists breaking up weddings or engagements, the romantic rival usually comes in one of three forms: preternaturally good-natured (Sleepless In Seattle, Sweet Home Alabama); explicitly evil (The Wedding Singer); or so goofily comedic that you don’t really invest in them as an actual character (Made Of Honor). When we first meet Diaz’s Kimmy, she seems like she could fall into either of the latter two categories. She’s young, girly, and overly eager to bond with Julianne—all of which is often code for “evil” when it comes to female characters, especially when they’re facing off against Julianne’s Cool Girl archetype. But Kimmy’s giddiness is so over-the-top, she also feels like she could wind up being the comic relief.

However, the film subverts our expectations about Kimmy as well. She’s not as naïve as first she appears to be, but she’s not evil either. She does have concerns about Michael’s close friendship with Julianne, but Kimmy’s only crime is trying a little too hard to bond with Julianne to overcompensate, while also keeping an eye on them. And although she’s goofy, the film grants Kimmy humanity as well. There’s a genuine emotional toll exacted by Julianne’s increasingly Machiavellian attempts to sabotage her wedding, but Kimmy responds with a grace that speaks well for her character. This is perfectly captured in a scene where Julianne tries to use Kimmy’s fear of karaoke to embarrass her in front of Michael. But Julianne’s plan fails: Although Kimmy is a truly atrocious singer, her conviction and guilelessness wins over the room anyway. Michael winds up being more impressed with his fiancé, not less.

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If My Best Friend’s Wedding has a flaw, it’s that its characters are all a bit thinly drawn. Ronald Bass’ screenplay seems more interested in macro subversions than micro details. We don’t, for instance, ever really get a sense of what draws Julianne or Kimmy to Michael, other than the fact that he’s played by Dermot Mulroney. But the talented performers make the material seem meatier than it is. Diaz makes the scatterbrained Kimmy so wonderfully earnest, the film gets away with underdeveloped elements like Kimmy’s utter dedication to Michael, or her quick forgiveness of Julianne. (The latter is, admittedly, a welcome beat in a genre with such a questionable track record of how it treats its female characters.)

There’s a strong argument to be made that My Best Friend’s Wedding is Julia Roberts’ all-time best rom-com performance. She’d already made several of them by this point, including Pretty Woman and Something To Talk About, and would go on to make many more. But My Best Friend’s Wedding feels like a distillation of the best elements of what all those other performances have to offer: the bubbly charm and physical comedy of Pretty Woman; the prickliness of Notting Hill; the vulnerability of America’s Sweethearts. The fact that you wind up empathizing with Julianne, even though she’s the ostensible villain, comes down to Roberts’ humanely capturing the raw emotions as Julianne’s lies are exposed.

That said, according to director P.J. Hogan, test audiences responded negatively to Julianne in an early cut. “They just couldn’t understand her motives,” Hogan explained to Entertainment Weekly in 2017. “They wanted her dead.” So Hogan made some changes, particularly in the third act. Most importantly, he beefed up the role of George, whom audiences did like, and whom Hogan saw as Julianne’s conscience: “Whenever she was being particularly devious, I’d have her phone Rupert’s character and he would call her out on it,” Hogan says. In the climactic car chase, George bluntly tells Julianne, “Michael’s chasing Kimmy. You’re chasing Michael. Who’s chasing you? Nobody. Get it?” Having George openly acknowledge Julianne’s bad behavior like this (something she occasionally does herself as well) allowed the audience to recognize Julianne as intentionally flawed, rather than being frustrated with her for being unintentionally unlikable.

The “gay best friend” archetype is somewhat less prevalent in actual rom-coms than rom-com parodies make it out to be, but George offers a fascinating example of it. He’s a character who, in some ways, plays right into stereotypes, while in other ways subverts them (not unlike My Best Friend’s Wedding as a whole). George is almost unsettlingly invested in Julianne’s personal life—very much the stereotypical “gay best friend”—but he’s her editor and mentor, too. He’s a few years older and already settled in a long-term relationship, which partially explains why he’s compelled to help her, and we do get a few glimpses of his life beyond being by Julianne’s side (dinner parties and erotic book readings, mostly). Everett, who is openly gay himself, brings real dignity and heart to George, and he all but steals the movie in a scene where he becomes drunk on the power of improvising ludicrous stories while posing as Julianne’s fiancé. (Like Roberts, Everett’s performance was nominated for a Golden Globe.) It’s not exactly groundbreaking LGBT representation, but it’s definitely better than it could’ve been.

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George is also crucial to the way My Best Friend’s Wedding perfectly calibrates its bittersweet, yet hopeful ending. Since the film isn’t building to one big happy ending like most rom-coms, it smartly offers a series of smaller emotional climaxes instead. Julianne individually makes amends with both Michael and Kimmy, then delivers a lovely toast to them both. As she’s left heartbroken and alone at the reception, we get the best scene in the whole movie: the reveal that George has flown in to surprise Julianne, which unfolds through the classic trope of a character talking to someone on the phone, only to learn they’re actually just across the room.

Though the scene is now among the most iconic in rom-com history, remarkably, it wasn’t part of the original script. My Best Friend’s Wedding was meant to end with Julianne meeting a potential new love interest played by John Corbett, then dancing with him at the reception. But this also contributed to test audiences’ dislike of Julianne; they didn’t want to see her immediately rewarded after everything she’d done. So George’s big surprise was added months later in reshoots as a compromise—one designed to keep Julianne humble, but also give her a different sort of happy ending. It’s now impossible to imagine the film without it. As Hogan says, “That one scene somehow gave the audience permission to forgive Julianne. Those last five minutes really made the whole movie work.”

For a movie so centered on the nature of friendship, it feels appropriate to end on a celebration of the best one Julianne has in her life. As I discussed in my column on Bridget Jones’s Diary, most rom-coms are about protagonists self-actualizing and receiving romantic love in return. But My Best Friend’s Wedding is about a romantic heroine who self-actualizes and doesn’t get romantic love in return. Julianne starts the film afraid of vulnerability and ends it having made herself as vulnerable as possible; she faces rejection and lives to tell the tale. Nevertheless, she learns that she has friends who will continue to love her, even at her very worst. (She even gets a beautiful moment of validation in her final goodbye to Michael.) In its own way, it’s as uplifting as any “...and they lived happily ever after.” Life goes on. Maybe love won’t always work out. But by god, there’ll be dancing.

Next time: Will Smith makes pick-up artists romantic in Hitch.