Before watching the movie:
I’ve been dimly aware of this as a relatively standout romantic comedy for a while, but I never really looked into it much. The idea of having to watch an old flame get married and how one copes with that is interesting, but as a romcom I don’t know if it’s going to have the kind of message I think would be more appropriate or if the old flame is going to leave the bride because true love.
Julia Roberts and Cameron Diaz are like two different generations of romcom royalty and it’s a little odd they’re cast opposite each other. Dermot Mulroney is a name I’ve seen around from time to time but even looking over his filmography I cannot remember seeing him in anything, and he looks like a stand-in for whatever more recognizable actor they actually wanted. I guess I’ve seen Rupert Everett in things other than Inspector Gadget, but that’s the only thing I ever think of for him.
After watching the movie:
Jules Potter is an intimidating New York food critic whose relationships don’t last because she doesn’t have time for love. She briefly dated traveling sportswriter covering the White Sox Michael O’Neal in college, but when she broke up with him, they realized they were too great as friends to completely sever the relationship, and stayed best friends for nine years. Around the time of her 28th birthday, she gets a voicemail from Michael saying it’s very urgent he speak with her, and she idly recalls how they once promised each other that if they both weren’t married by age 28, they’d marry each other. But Michael’s news is that he’s met someone and he’s getting married right away, why hasn’t Jules been returning his calls for the last month, please come out to Chicago for the wedding. Suddenly feeling an ownership over Michael from the prior claim, Jules drops everything for the trip. Kimmy is a 20 year old junior college student and the daughter of the owner of the White Sox, and she immediately asks Jules to be her substitute Maid of Honor, though everyone agrees if there hadn’t been a vacancy she should’ve been a groomsman. In an attempt to sabotage the relationship, Jules suggests to Kimmy that her father should offer Michael a comfortable office job with the White Sox PR, settled down close to the family in Chicago, which is absolutely the kind of job Michael would hate. While it does hit a nerve, the two recover amazingly quickly, so Jules has to continue plotting how to destroy this relationship and win Michael back.
In a rare turn, I found myself watching a romcom I actually wasn’t sure I could predict the outcome of. While romcoms are usually about the unfitting relationship being the conflict keeping the two leads together, Jules’ stated goal of breaking them up meant that, “Jules wants Michael, Jules breaks up Michael’s wedding, Jules gets Michael” isn’t a strong plot because a story where the first plan works is too simple. However, the movie was also very, very good at setting up romance beats between Jules and Michael and building up why Michael and Kimmy don’t fit together the way couples in movies are supposed to. So I was a little uncertain whether the wrinkle in the plot would be “Jules’ plan hurts Michael and she learns to let him go” or “Jules decides to let Michael go, but the momentum of their reunion pulls them back together in a way that organically absolves Jules of blame”. The former is the messaging I would encourage, the latter is what usually happens in romcoms.
One thing to this movie’s slight detriment is that it’s a little too in love with its music. There are at least two show-stopping musical numbers, one the non-diagetic title sequence and one the wedding party lunch, that go on about twice as long as they should have. That’s not to say the music selection isn’t good, it’s just the problem I always have with music in shows. Unless it’s an integral part of why the work exists, it should get out of the way once it’s served its purpose.
It feels like an attempt was made to make the movie feel like Chicago, but I’m not sure it quite gets there. Outside of some particulars of the White Sox, the only “that’s Chicago” moment I noticed was when Jules and Michael eat chili dogs on some apartment steps. Kimmy’s family being so wealthy, they’re fairly removed from a lot of what gives Chicago its character and exist in a generic “rich people” world that could’ve easily been in California, upstate New York, New England, or really a lot of the US.
The substance of the story is a lot more complicated and grown up than just about anything else in its genre. It wasn’t exactly the story I would tell, but it’s roughly the story I hoped it would be. It’s a lot of fun, the romantic beats connect just the way they’re supposed to, and it actually kept me guessing in a world of plot by numbers. I respect this movie as a 90s classic that’s going to endure as long as peoples’ feelings are too messy for the options they’re presented to fit into.