Top 10 Behind-the-Scenes Secrets from My Best Friend's Wedding

Considering she’s the star of the film, it probably comes as no surprise that Julia Roberts was one of the first actors cast in her role. And while this kind of work is usually left to producers and casting directors, it turns out that, in this case, Roberts actually had a major say in which actors she was going to work alongside. She advocated for Cameron Diaz to be cast as the young and optimistic bride-to-be Kimmy and even helped choose Dermot Mulroney to play the love interest of both women. It was one of Diaz’s breakout roles, and she has Julia Roberts to thank for it!

In an interview with the Huffington Post years later, actor Dermot Mulroney, who plays Michael in the movie, revealed why he thinks “My Best Friend’s Wedding” continues to stand out despite so many romantic comedies having been released since then. He says that the key is that the plot isn’t focused on a happy ending between the two romantic leads, but is rather a farce of sorts, where the audience gets to watch Julianne fail spectacularly at her task of breaking up this wedding. Modern rom-com creators- take note!

Back in 2015, it was revealed that ABC was in the process of developing a TV version of “My Best Friend’s Wedding,” which would be a continuation of the story rather than a reboot. Sadly, since the announcement, there haven’t been any major developments and we can only assume that, like so many others, this project has stalled, likely to never see the light of day. There was also a sequel that was discussed where Julianne would try to break up George’s wedding; we have a feeling that would be a totally welcome addition to the franchise!

By the time “My Best Friend’s Wedding” was being filmed, Julia Roberts was already a major movie star, so it probably comes as no surprise that it was tricky for her to film scenes on location in Chicago without getting mobbed by fans. One funny example is the ferry scene, where it seems like something is finally going to happen between Julianne and Michael. The boat they’re on keeps passing under bridges, but when they were shooting they had to contend with fans screaming Julia’s name, interrupting the shot each time.

One of the most memorable and arguably most important scenes in the film is when Cameron Diaz’s character, Kimmy, is dragged into the spotlight to perform at a karaoke bar. Suffice it to say, karaoke is the last thing she wants to do. It’s one of the first times Julianne tries to mess with Kimmy, who still manages to come out unscathed. But if her terror looked real, it’s because it was! The actress was truly dreading singing in front of so many people, even though it was supposed to be bad. Diaz said, "I was terrified to do that scene, for real. I allowed the true terror of singing in front of people to be alive in me”.

If you ask fans whether Michael and Kimmy’s marriage would have worked out in the long term, you’re likely to get mixed responses. Kimmy was, of course, barely out of her teens when the two tied the knot, and it’s not like they exactly had a lot in common. But pessimism about divorce rates aside, the members of the cast largely believe that these two would still be happily married! In a 2019 interview with Entertainment Weekly, Dermot Mulroney said, "It supports the whole theory that it's the right girl for him, right guy for her, you know?"

In the final version of the movie we all know and love, the spotlight is often stolen from the main love triangle by Julianne’s gay best friend George, played to perfection by Rupert Everett. But originally, this character was going to have a much more secondary role. And in the beginning, the character’s name was Digger! Now it’s almost impossible to imagine the movie without George playing such a prominent part. And it certainly worked out for Rupert Everett because he ended up getting nominations for Best Supporting Actor at the BAFTAs and the Golden Globes that year.

In a 2019 interview with Entertainment Weekly, P.J. Hogan, who directed “My Best Friend’s Wedding”, revealed some behind the scenes casting info that caught us by surprise. He said that he asked one of his friends from the industry, Russell Crowe, to read for the part of Michael, which he ultimately wasn’t the right fit for. Similarly, Julia Roberts wanted Benicio Del Toro to try out for the part of George, which, in hindsight, is honestly quite hard to picture. In the end, the casting was perfect and we couldn’t imagine it any other way.

Just like for the male leads, there was a lot of debate about who would play Kimmy. Major stars like Drew Barrymore and Reese Witherspoon both tried out for the role, which ultimately went to Cameron Diaz. Comparing the star power of Diaz to Roberts, the director said, “I thought this is going to be much more of a battle royale if there are two stars fighting over this guy. You can’t choose between them.” And while Julia Roberts was involved in the process from early on in production, there was a time when Sarah Jessica Parker was actually considered to play Julianne. Honestly, we can kind of picture that one, though we still think the final casting worked out for the best.

When this film was originally shown for test screenings with audiences, they had a terrible reaction to the ending, in which Julianne met a friend of Michael’s at the wedding (played by John Corbett), and it was implied that there was new romance on the horizon for her. The movie’s director said, "The focus group didn't want Julianne to have a happy ending. They still hadn't forgiven her”. So they ended up doing some pretty extensive reshoots, which changed the ending to the one we’ve come to know and love today.