When Julia Roberts Played a Friendless Villain

My Best Friend’s Wedding, Twenty Years Later

Illustration by Sarah Morton

In the summer of 1997, we were forewarned of the surprising outcome of My Best Friend’s Wedding almost exactly halfway through the film: Our unlikely hero Julianne “Jules” (Julia Roberts) is sending off her friend and confidant George (Rupert Everett) after he’s come to her rescue in the midst of her plot to break up a wedding. His final advice is to do what’s obviously for the best: She needs to tell her best friend, Michael (Dermot Mulroney), that she is in love with him, and let him decide for himself what he wants.

“What will he do?” asks an anxious Jules.

George walks back over to her and tells us all the ending of this blockbuster romantic comedy, even if we won’t believe it until we see it:

“He’ll choose Kim,” George says. “You’ll stand beside her at the wedding, kiss him goodbye, and go home. That’s what you came here to do. So do it.”

When this is exactly what happens 50 minute later, we’re still gobsmacked because that’s not how these movies go. For once, our leading lady doesn’t get the guy, and thank god for that. It’s terrible to even imagine the opposite. If Jules had successfully broken up a perfectly happy couple the week of their wedding and got the guy, this movie couldn’t have ended any other way than with an homage to the final shot of The Graduate, with the newly-reunited couple couched in shock and regret. Jules doesn’t want to marry Michael, a man she claims is her best friend despite going months at a time without speaking to him — she wants to be chosen, to win, because she’s kind of a terrible person. It’s highlighted all the more brightly by the fact that Michael’s fiancé, Kimmy (Cameron Diaz), seems perfectly sweet.

“Michael’s chasing Kimmy, you’re chasing Michael,” George shouts at her in the climax of the movie, culminating with a bread van vehicle chase down Michigan Avenue. “Who’s chasing you? Nobody. Get it? There’s you’re answer. Jules, you are not the one. You have a small but distinct window of opportunity to do the right thing.”

What kind of romantic comedy bluntly tells its audience that its leading lady isn’t “the one”? One that stars a near-friendless anti-hero, a full decade before Don Draper or Walter White came along.


As Roger Ebert wrote June 27, 1997, a week after the movie was released, “One of the pleasures of Ronald Bass’ screenplay is the way it subverts the usual comic formulas that would fuel a plot like this. It makes the Julia Roberts character sympathetic at first, but eventually her behavior shades into cruel meddling.”

I was 11 years old in 1997, and I rooted for Roberts then. I idolized her as a pre-teen. My junior prom dress was the exact color as Roberts’s signature maid of honor dress, though I doubt there was anywhere I could have bought, or afforded, a mermaid cut gown in southeastern Ohio — empire waists were much more 2003, anyway.

I watched every Roberts movie I could get my hands on. My mother was not impressed by my interest in Pretty Woman, but watched Mystic Pizza and Steel Magnolias with me. I wanted to dress like her, speak like her, smile a 1,000-watt tooth-filled smile like her. I would stare in the mirror of our blue upstairs bathroom willing my tangled, dark blonde curls to be smooth like hers, trying every hair product with the word “curl” in its ad copy. Roberts taught me to love my curls at an early, and tough, age. Alternately, I’m pretty sure if I go back far enough, I can trace my teen smoking to her character in My Best Friend’s Wedding, alongside fellow curly-haired late-90s anti-hero, Carrie Bradshaw. (Though, unlike Carrie, we’re shown that Jules smokes Marlboro Reds, not Lights — what clearer way to indicate that she is a man’s woman?)

In this sense, I also strongly identified with Jules’s desire to be just like one of the guys. At a White Sox game early in the movie (at then-Comiskey Park), Jules is the ultimate Cool Girl: She brings her male cohorts a tray of beers; she wears a midriff-baring top; she flirts. She’s like a lot of girls I knew, myself included, when they were in college — working for years to be liked by men, only to look around and realize all her friends’ girlfriends hate her and she hasn’t made any strong female bonds by graduation day. I can relate to that, in a big way. The difference is, I course-corrected once I left school, and Jules is 28. Since Kimmy actually is in college but acts far more mature than Jules (and, arguably, Michael), you could be forgiven for believing their ages were the other way around.

Jules prides herself on not being traditional, on not acting in the ways she believes other women do. Her arrogance in this belief comes through in the famous creme brulee versus Jell-O conversation she has with Kimmy the morning of the wedding — guess who’s supposed to be represented by which? Jell-O, after all, makes everyone comfortable.


As much as I love George, Jules could have benefitted from some well-grounded women friends in her life, and maybe some Shine Theory. With the support of other women, she might have skipped that wedding altogether and gone off on a girls’ beach weekend or something, drinking white wine spritzers in lieu of attempting to break into downtown Chicago office buildings. As far as the audience can see, no women are exactly eager to get brunch with Jules, despite her being a professional food critic. Instead, Jules is a successful, hard-working careerist with almost no friends, aside from George and the estranged Michael.

Alternately, I can only imagine the power friendship she and Kimmy could have forged had they decided to set their differences aside! Despite being pitted against each other the entire movie, they do manage to have some fun moments together.

“I’ve never had a sister,” Kimmy gushes upon meeting Jules. Later, the two bond in an elevator at the Chicago Hilton over their shared experiences with Michael’s snoring and other flaws. In this scene, Kimmy is even willing to admit some envy on her part when it comes to Jules, a vulnerability and self-awareness Jules can’t seem to stomach owning up to herself. It takes me back to all the times I’ve met an ex’s new partner and how hopelessly uncontrollable the urge feels to compare myself to them.

“I had to face up to all of my competitive drives, and believe me, I’ve got them,” Kimmy says. “After all, what am I gonna be jealous of you for the rest of my life? And the answer was so simple: You win. He’s got you on a pedestal, and me in his arms.”

Even Jules can’t help but kind of like Kimmy.

“If I didn’t hate her, I’d adore her,” she grudgingly admits to George.

Kimmy simply radiates likeability. At a karaoke bar, Jules’s plan to embarrass her backfires because Kimmy is so gracious and cognizant of the fact that she is a terrible singer. Even when she bombs, she still manages to win over the crowd. Kimmy may be naive, appearing to fall for a few of Jules’s deceptions, but that and her young age aside, she’s maybe the most mature among the three people involved in this love triangle. Her only clear flaws seem to be that she can’t sing and is apparently a scary driver, a tired trope about women characters that has not aged any better since 1997.

And finally, the endearing “cat fight” scene toward the end of the movie seals the deal as far as it goes what I see as a lost opportunity for friendship between the two women. After Kimmy sees Jules kiss Michael and just before the bread van chase, she flees the scene. Jules tracks her down at Comiskey Park after getting a tip-off that she was spotted “crying into her nachos” in the luxury box. Jules finds her in the bathroom, and for the first time in the movie, Kimmy loses her patience at last, storming out of a bathroom stall.

“You kissed him! At my parents’ house! On my wedding day!” she shouts, as a crowd of women gather to watch the fireworks. “I love this man and there’s no way I’m gonna give him up to some two-faced, big-haired food critic!”

Knowing she’s lost her audience, Jules acquiesces.

“Alright, alright, I kissed him!” she admits to the mob forming around them. “I tried to steal him. I lost. … I’d like to take you to the church so you can walk down that aisle and marry the man of our dreams. Because he sure wants to marry you.”

Kimmy freezes but then hugs her, and the cat fight is over, the crowd clapping appreciatively, politely. And once again, it’s truly unexpected! It’s not your typical scene of two women fighting over a man, and I appreciate it more now through a 2017 lens than I did twenty years ago.


That said, there are some aspects of My Best Friend’s Wedding that have aged less gracefully. There’s a glaringly clunky technology plot device used toward the end of Jules’s scheming that is laughable now, but it can be forgiven when compared to some of the ways the movie’s characters are handled. No matter what Kimmy and Michael think they’ve mutually agreed upon between the two of them, there are some big concerns for their future.

Kimmy and Michael’s relationship has clearly been a short one so far, though and it’s never really said how long they’ve been together. Where and how did Michael, a 28-year-old sports reporter, meet an architectural undergrad at the University of Chicago? And does Michael really not know until the week of their wedding that Kimmy can’t sing? Why is it so imperative that she must drop out of school when she clearly doesn’t want to?

Kimmy is so young — she is, in fact, the age that both Jules and Michael were when they first met each other in college nine years earlier. It’s gross to me that Michael calls his future wife “kid,” although for what it’s worth, he does the same thing to Jules. (Still gross.)

Another problem for Kimmy and Michael is that Michael seems super inappropriate in terms of his behavior toward Jules. Early on, he walks in on her when she’s standing in just her underwear. When she grabs a sheet to cover up, he reminds her, “I’ve seen you a lot more naked than that.” “Things are different now,” Jules replies. This, along with a later joke about “a hot affair we’ll have every six months” after the wedding, has me pretty well convinced that these two have been hooking up on and off over the years since college.

Does Michael want to get married? We never get a definitive answer. The romantic architectural boat tour scene has long been one of my favorites because of the sweet song and dance that takes place on deck, but it also briefly sheds some light onto Michael’s current headspace.

“This could be our last time alone together,” he seems to lament, indicating that maybe he’s experiencing some pre-wedding jitters. “You commit to this wedding and there’s all this momentum, and you forget you chose it.”

Michael comes off significantly less sympathetic when he’s chiding Kimmy for wanting him to quit his low-paying, but satisfying job, the one that also serves as the reason she must leave school. When she suggests he take a more stationary gig with her father’s company in Chicago, he balks.

“What, all of a sudden I’m supposed to drop out of school, forget my family, forget my career, forget about all the things I had planned for my life?” Kimmy says.

“Forgive me for screwing up your plans,” Michael darkly replies. When she gets upset, he sarcastically calls himself an “insensitive, sexist asshole.”

To my chagrin in 1997, but much more so now, Kimmy sobs and apologizes. She begs him to forgive her, and he does. No one should feel great about this resolution.

Still, while these points are all at least somewhat problematic, I would argue that gender politics of My Best Friend’s Wedding could certainly be worse — especially when compared to, say, the aforementioned Pretty Woman, which came out seven years earlier and leaves much to be desired in this area. My Best Friend’s Wedding’s opening credits dance number, showing a bride and three bridesmaids singing “Wishin’ and Hopin,’” is clearly meant to be tongue-in-cheek. That’s made all the more evident by the fact that feminist artist Ani DiFranco is the one singing the track. Though Jules is considered distant and uncomfortable with affection, she is still portrayed as an independent careerist. And while I can’t speak to how a gay men may feel about George’s portrayal, it’s worth noting that his role was expanded in order to do damage control, making Roberts’s character look more sympathetic in the film’s final few minutes. Technically, this movie passes the Bechdel test, but just barely — at one point, Jules has a conversation on the phone with a female cousin of Kimmy’s, in which the two discuss Kimmy’s whereabouts.

And finally, it’s slightly refreshing to realize that the least-developed lead role in this movie is Michael’s — we know far more about what Jules and Kimmy think and feel. Aside from the boat scene, we don’t know much about what’s going on inside the leading man’s head, or even why Jules wants him so bad — we just know he is The Thing To Be Won. It’s an interesting gender flip to see for a change.


The film’s unconventional ending made My Best Friend’s Wedding memorable, and helped it earn its distinction as #12 among the top-grossing romantic comedies of all time — but what makes it still so enjoyable, twenty years later?

The music was perfectly selected, with heavy borrowing from Dionne Warwick and Burt Bacharach. I can’t think of this movie without remembering the sheer joy-filled, Everett-led scene halfway through, when the camera pulls back to pan across an entire seafood restaurant full of people chiming in to sing “I Say A Little Prayer” together — complete with a couple employees swaying their giant, red lobster claws in the background.

Additionally, the all-star cast was well chosen, and Roberts herself specifically picked Mulroney and Diaz to play opposite her. While Diaz has done a variety of big roles over her career, Mulroney’s part in My Best Friend’s Wedding may be one of his most recognizable. There are also a handful of memorable cameos, including Rose Abdoo as a seamstress and Paul Giamatti as a wise bellhop at the Drake Hotel. Chef Charlie Trotter plays himself in the first scene that introduces us to Jules and George while they’re working on a restaurant review.

And personally, for me, the city Chicago helps make this movie stand out — more movies should be shot in the Midwest. But, as someone who spent five years there, I admit to being partial. The boat tour scene alone will make any former Chicagoan at least a little sorry they left.


The movie ends just as George said it would, with Michael and Kimmy getting married. At the reception, Jules gives a speech, noting that “my best friend, has won the best woman.”

The movie’s original ending had Jules meeting a man at the wedding, played by John Corbett — maybe Carrie Bradshaw’s tastes weren’t so different after all? However, at the expense of an Aiden Shaw appearance, test audiences were so upset with Jules that they didn’t want her to meet someone new. Instead, we get one last truly delightful moment with George, who crashes the party to take Jules’s mind off things.

“I did what I came here to do,” Jules tells him. “I said goodbye.”

George’s final words during this nontraditional ending hold up today just as well as they did in 1997.

“Life goes on,” he concludes, taking her hand. “Maybe there won’t be marriage, maybe there won’t be sex. But by god, there will be dancing.”

Meryl Williams is an Ohio-based writer who loves Rilo Kiley and roller derby. Sign up for her awesome TinyLetter.