‘My Best Friend’s Wedding’ retrospective: The rom-com that flipped the genre on its head and cemented Julia Roberts’ status as a full-fledged star

The 1997 romantic comedy My Best Friend’s Wedding is unhinged in many ways. For starters, it begins with an opening credits musical sequence to Burt Bacharach and Hal David’s “Wishin’ and Hopin,’” the first of many musical moments in the film. But that’s only a preview of how it turns the entire genre of the rom-com on its head. P.J. Hogan’s film, with a script by Ronald Bass, asked audiences to be honest about how the crazy extremes that rom-com heroes and heroines go to are often more immoral than romantic and to consider what happens if the heroine doesn’t win the guy in the end. 

Jules (Julia Roberts) is a New York City food critic, first seen out to lunch with her editor George (Rupert Everett). She gets an urgent message from her best friend Michael (Dermot Mulroney), a sports writer with whom she attended Brown University years before. They had a one-month relationship, but decided they were better off as best friends. Best friends who made a blood oath marriage pact that they would get married at 28 years old if they were both still single. 

Which, for the record, is absolutely insane. Even for a film made in the 1990s, 28 is a strange age to choose for a marriage pact. It’s essentially letting the other person know that you hope you will end up marrying them. And why 28 and not 30? And Michael decides they should seal this pact with a literal blood oath? This story clues us into just how crazy Jules and Michael are, which makes everything that follows less surprising. 

Jules is nearing her 28th birthday, and George suggests that Michael is reaching out to fulfill the promise they made years ago. So she’s shocked that he’s inviting her to his wedding, which is occurring in Chicago in just four days. Jules sets out to break up the marriage and win Michael back now that she’s suddenly realized she can’t live without him, but she’s in for another surprise.

Jules is nearing her 28th birthday, and George suggests that Michael is reaching out to fulfill the promise they made years ago. So she’s shocked that he’s inviting her to his wedding, which is occurring in Chicago in just four days. Jules sets out to break up the marriage and win Michael back now that she’s suddenly realized she can’t live without him, but she’s in for another surprise. 

Michael’s fiancé Kimmy (Cameron Diaz) is the stereotypical rival woman: young, rich, blonde, and beautiful. But she’s also endearingly warm and friendly, even if she is a 20-year-old junior at the University of Chicago. That eight-year age gap between her and Michael is highly questionable since she’s still a student. How did the two meet? But she’s so enthusiastic about meeting Jules and asks her to be her maid of honor since her best friend shattered her pelvis and can’t make it. It’s a character that many rom-coms would have made detestable, but it’s impossible to hate sweet Kimmy. 

Julia Roberts was already a star after the success of Pretty Woman in 1990, but My Best Friend’s Wedding cemented her status as one of the biggest names in Hollywood that could draw crowds to the box office. The fact that the character of Jules remains engaging despite her horrific actions as she tries to lie and cheat her way back to Michael’s heart is entirely due to Roberts’s charisma. She spends the entire film trying to come between the couple, despite how they continually find their way back to each other, and crosses lines that even a rom-com can’t ignore. 

But while Jules might be the villain, Michael is equally guilty in a way that I’m not sure the film fully reckons with. He flirts with Jules just as much as she does with him – in front of his young fiancé. They flaunt how well they know each other, and he tells her that she looks good without clothes on when he walks in on her trying on her maid of honor dress. Jules might be trying to break the couple up, but Michael makes no secret that though he loves Kimmy, he still carries a torch for his “best friend.” 

While Kimmy is a victim of Jules’s schemes and Michael’s unwillingness to set proper boundaries, she handles it gracefully. Diaz was at the beginning of her acting career, but she lights up the screen every time she’s on it, convincing the audience why Michael fell for her. Kimmy is a big enough person to put Jules in a beautiful lavender gown for her maid of honor dress, and she’s willing to give up her architecture dreams to follow Michael around for his unstable job. She recognizes the situation for what it is, telling Jules, “He’s got you on a pedestal, but me in his arms.” 

One of the film’s most memorable moments is when Jules tries to humiliate Kimmy at a karaoke bar by forcing her into singing. Diaz nails her part as Kimmy’s embarrassment in her horrible voice fades into good showmanship and she wins over the whole crowd despite her bad vocals while putting on a proper performance of “I Just Don’t Know What to Do With Myself.” Michael is entranced, and even Jules looks reluctantly impressed. 

But the true star of the show in this film is George, played by a suave and dashing Everett. He is the voice of reason throughout, continually telling Jules that the only thing she can do is be honest with Michael about her feelings while also warning her that he’ll choose Kimmy in the end. The way that he continually shows up for Jules and supports her despite her erratic behavior proves that it’s him, and not Michael, who is her actual best friend. 

He plays along with it when Jules hatches a crazy scheme to tell Michael that she and George are engaged, which leads to him leading a fantastic singalong of “I Say A Little Prayer for You” at the rehearsal lunch. Everett’s performance is the strongest of the four, providing a solid pillar for the rest of the cast, just as George does for Jules. It’s remarkable to see a gay character in a 1990s film who is more secure in himself and his sexuality than the straight leads. 

The most significant way that My Best Friend’s Wedding refuses to play by 1990s rom-com rules is by denying its heroine a happy ending. Though she does confess her feelings, Michael still marries Kimmy, and Jules finally accepts the situation with what little dignity she has left. It’s George who shows up to dance with her at the wedding, a reminder that sometimes your ‘person’ may not be someone with whom you’re romantically involved. 

My Best Friend’s Wedding could be a feminist masterpiece, refusing to play by the rules of the genre and letting each person get what they deserve. However, in 2022, one thing doesn’t sit well: 20-year-old Kimmy is saddled with Michael. However attractive Mulroney might be, it doesn’t make up for his inability to set boundaries and his willingness to have his wife abandon her career goals in favor of his. Instead, it’s the sort of end-of-a-rom-com wedding where you can’t hope but think – and maybe hope – that the marriage would end in divorce within a few years. 

Over the past twenty-five years, My Best Friend’s Wedding has remained part of popular culture, continuing to inspire fear in girlfriends of men with female best friends. (I promise we’re not all like this!) Before COVID struck, there were even plans for a London musical adaptation of the film. After all this time, it continues to go against the conventions of a rom-com, and it would hold up splendidly if it didn’t punish poor Kimmy by having her end up with a man who is a walking red flag.

My Best Friend’s Wedding was released by Columbia/TriStar on June 20, 1997. It is currently available to rent or buy on Prime Video as well as Google Play, AppleTV, Vudu and more.