20 Years Later, ‘My Best Friend’s Wedding’ Is Surprisingly Mature in Its Immaturity

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My Best Friend's Wedding

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In the summer of 1997, Julia Roberts was America’s Sweetheart in dire need of a comeback. Aside from the modest hit Something to Talk About, Roberts’s last five movies were a sad collection of unfunny comedies (I Love Trouble), ill-advised dips into genre fare (Mary Reilly), and unsuccessful awards-bait (Michael CollinsEveryone Says I Love YouPret-a-Porter). She needed a movie that reminded American audiences why they fell in love with her in the first place. Which is why it’s so surprising (and to her credit) that Roberts went and made My Best Friend’s Wedding, a romantic comedy, yes, but perhaps one of the most courageous romantic comedies in memory in that it dared to make its gorgeous female protagonist an unambiguous villain.

If you haven’t seen it — and first of all, how dare you — the plot of My Best Friend’s Wedding goes like this: workaholic food critic Jules (Roberts) gets news that her longtime platonic bestie Michael (Dermott Mulroney) is getting married, which is exactly when she realizes that Michael is the love of her life. And now she needs to sabotage his wedding to Kimmy (Cameron Diaz) and win his affections all in the course of one whirlwind Chicago weekend. That Jules frequently acknowledges the fact that she’s the villain in all of this is a refreshing bit of self-awareness on the film’s part, but it doesn’t change the fact that it is VERY hard to root for Jules throughout the whole movie.

That, of course, is the magic of My Best Friend’s Wedding, a romantic comedy where the heroine is largely despicable, where the romance that we’ve been conditioned to root for is poisoned at the root, where the protagonist ends up alone, and where that, in fact, is the happy ending. It’s an act of atonement for every fraudulent romance we’ve ever had to sit through where the guy and the girl get together solely because they’re the two stars. Throughout the film, Jules behaves with massive immaturity (even though she is only 28, which we’ll get to that, just you wait), refusing to see reality and behaving like she’s the only person who exists in the world. But the film is all the more mature for being the rare romantic comedy that recognizes this and adjusts its audiences expectations accordingly. Director P.J. Hogan (Muriel’s Wedding) and screenwriter Ronald Bass (Oscar-winner for Rain Man) managed to deliver a subversion of the genre in the middle of a movie that nonetheless luxuriates in the pleasures of that very genre. It is a movie that has its wedding cake and eats it too.

On the occasion of its 20th anniversary, then, here are 20 things about My Best Friend’s Wedding that make it one of the most essential romantic comedies of its (or any) era. Watch it again as soon as you possibly can.

20 Things About My Best Friend’s Wedding on Its 20th Anniversary

1. For starters, it’s the rare rom-com that begins with a candy-colored cake-topper-inspired production number set to an Ani DiFranco cover of the Burt Bacharach tune “Wishin’ and Hopin’.” Bacharach is the muse of this movie, a quirky little affect that never stops paying off.

2. A moment, if I may, to point out whatever the hell this artist’s smock is that Jules is wearing in her first scene, a scene where she is on the job as New York’s most fearsome restaurant critic. “Oh, but she’s probably going undercover as some kind of tourist rube in order to throw off the staff,” you rationalize. But then why does the entire restaurant staff hold their collective breath until she renders her verdict (“inventive and confident”)? I ask you why!

photo: Tri-Star Pictures

3. So let’s address the elephant in the room and what is consistently the most ridiculous/insane thing about this entire film, and we’re confronted with it bright and early: Jules and Michael made a pact when they were younger that if they were still single at age 28, they’d get married. TWENTY-EIGHT! Even considering the fact that idiot college kids might think that 28 is incredibly old and time to settle down, it’s utterly crazy that a marriage pact for 28-year-olds is the peg this movie hangs its plot on. (It’s equally crazy that Roberts likely filmed this movie when she was actually 28 years old. People have gotten MUCH younger over these last 20 years.)

4. I mention this a lot about movies made in this era, but it never ceases to amaze me how much smoking used to happen in movies. I’m ashamed to say that I desperately miss it!

5. After landing in Chicago and enduring Kimmy’s insane driving (her character, by the way, is TWENTY YEARS OLD; how is nobody objecting to this UNDERAGE MARRIAGE), Jules meets Kimmy’s only other bridesmaids, two distant debutante cousins, “vengeful sluts” (a moniker that only ever half-suits them) played with delightful vulgarity by Carrie Preston and Rachel Griffiths. Griffiths, it should be noted, was also in P.J. Hogan’s Muriel’s Wedding, delivering one-half of the greatest ABBA performance in film-history, do not @ me, cast of Mamma Mia!

6. As good as Roberts is in this movie, Cameron Diaz almost manages to match her. What initially seems like it might be a shaky performance ends up revealing a character in Kimmy who is always a bit savvier than she’s letting on. Yes, she still falls for all of Jules’ machinations, but she knows enough to be keeping some kind of an eye on her. The way she subtly shades Jules while she’s trying on her bridesmaid’s dress (“you wouldn’t be comfortable unless you were distinctive”) suddenly makes the movie so much more interesting.

7. The specifics of Jules’ plot to derail the marriage aren’t worth getting into, except to say that the script is smart about using repetition so that the audience gets the gist of it. “If San Antonio sweeps Sacramento” is an essentially meaningless phrase but it keeps reminding the audience that Michael’s job and Kimmy’s vision of their future has some snags in it, and Jules means to exploit those snags.

8. It is highly recommended that once in your life, you find a reason to quote Julia’s perfect line delivery of “I’ve got moves you’ve never seen.” You’ll only get one chance to do it right, though, so choose wisely.

9. How can I put into words the perfection of the karaoke scene. For one thing, it gets so much more right about karaoke than it gets wrong, which is such a rarity in movies. It is unrelenting in how terrible at singing it allows Kimmy to be. Diaz is fiercely committed to being a world-class awful singer, and she pulls it off spectacularly. (Between this scene and all of In Her Shoes, I’m ready to say that Diaz is at her best when she has zero regard for making her character look good. The subtle turn the room takes from being hostile to Kimmy for her lack of talent to being supportive of Kimmy for her admirable effort is almost mathematical in its precision. They get on her side at exactly the right time. And in what remains my favorite shot in the film, Jules cannot help but get on Kimmy’s side as well, delivering the greatest slow-clap in film history.

10. The quickness with which Michael flips over to anger when Jules is able to instigate an argument between him and Kimmy over her wanting him to take a job at her father’s company is frankly unsettling. More on this later.

11. So Jules gets desperate and calls Rupert Everett’s George in as reinforcement. George is an interesting character. He falls squarely into the center of the GBF (Gay Best Friend) trope, a trope that absolutely has in the past reduced gay men to mere accessories for women protagonists. But specifically in this movie, George managed to transcend that. No, he doesn’t get an independent story or a boyfriend or a sex life. That’s not what the movie is about. But he’s also no mere glorified gal-pal. He’s an essential element of the story, the one true adult in the room, and in many ways the film’s true voice.

12. That said, Rupert Everett camps it up WILDLY during the “I Say a Little Prayer” singalong, the one point in the movie where Hogan takes the liberties of the romantic-comedy genre and goes overboard. That said, it’s wildly charming, and everyone remembers it fondly, and what are genre conventions for if not for writing yourself a permission slip for a big, unrealistic singalong number?

13. The gondola scene is the closest the movie gets to making you want Jules and Michael to get together. The music, the scenery, the scar on his lip matching that thing where she doesn’t have the divot just below her nose. Everything works. I truly appreciate being manipulated like this.

14. Another reminder that sometimes the rom-com genre writes you a permission slip to be a hack for a minute: pretty ladies falling down:

15. Can we take a moment to admit to ourselves that, as much as Jules and Michael shouldn’t be together (if only because she shouldn’t be rewarded for all the underhanded things she’s doing), Michael and Kimmy should also probably not be getting married. Even after all the fighting, they never resolve the fundamental disconnect between him wanting to remain a nomadic sportswriter and her wanting to, oh, finish college and have a career and achieve the legal drinking age. He’s 28, and she’s 20, and neither one of them are able to communicate to each other what they want without getting angry (him) or crying (her). This is a bad marriage. More like My Best Friend’s FIRST Wedding, am I right?

16. That crème brûlée metaphor is just a masterpiece of a scene. On paper, it’s a fun little nod to Jules’ profession (28-year-old most feared food critic in New York City, remember). In practice, however, it’s a brilliant piece of broad comedic banter between two of the biggest stars of the past 25 years.

17. Sigh. The “choose me, marry me, let me make you happy” is so hard to watch. Not because it’s bad, but because it is so unflinchingly hard on her. Also, even as someone who loves Grey’s Anatomy, it’s more than a little shameless how Shonda Rhimes ripped this scene off ten years later.

18. P.J. Hogan has talked about how beefing up the George role ended up saving the film, and part of that was including the phone call where Jules tells George how she’s chasing Michael, who is chasing Kimmy. “But who’s chasing you?” he asks, then answers it himself: “nobody.” It sums everything up perfectly.

19. Okay, I like the baseball-park-bathroom showdown between Kimmy and Jules because it’s cathartic and also defuses a bit of the audience’s antipathy towards Jules by letting their anger be reflected in the pissed-off expressions of the other women in the ladies’ room. But I’m going to need independent confirmation that the ladies’ restrooms at Comiskey Park were ever this spacious or well-trafficked.

20. That ending. That damned perfect ending. Endings are hard! You want to wrap things up, but not too neatly. You want to leave the sense of life going on, but commemorate the changes that have occurred. You want it to be happy, but with an undercurrent of something else (melancholy? cynicism? absurdity? the mundane?). That My Best Friend’s Wedding ends without the couple you expect to get together getting together, it has to go for something else. Famously, it was originally supposed to end with Jules meeting someone new at the wedding (played by Sex and the City‘s John Corbett, of all people). Blessedly, we get what we got instead: George miraculously showing up like an impeccably dressed gay guardian angel. If the arrival of the GBF feels a little too perfect, George’s monologue to Jules is perfectly calibrated: beautiful but decidedly clear-eyed. There may not be marriage. There may not be sex. But by God, there’ll be dancing.

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