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Asking the Important Questions About Michael’s Sportswriting Job in ‘My Best Friend’s Wedding’

Not only is Dermot Mulroney’s character the apple of both Julia Roberts’s and Cameron Diaz’s eyes, but he’s also a [checks notes] beat reporter who covers a thousand different teams and sports and is in line to inherit the Chicago White Sox. What the heck is going on here?

TriStar Pictures/Ringer illustration

When you find the theme week you want to spend the rest of your life with, you want the rest of your life to start as soon as possible. Thankfully, The Ringer hereby dubs this week Rom-Com Week, a celebration of one of the most delightful, captivating genres in film. Head to the top of the Empire State Building, order what she’s having, and join us as we dig into everything the rom-com has had to offer over the years—including this piece on My Best Friend’s Wedding, originally published in 2020 as part of The Ringer’s Return to Blockbuster Season.

Sportswriters are not a stereotypically sexy group. If you made an amalgam of everybody’s first thoughts when asked to picture “a sportswriter,” you’d get a middle-aged guy wearing a sweater vest that used to fit, about 150 complimentary pregame chili cheese dogs ago. We sportswriters love sports, but there are generally a few pointed reasons why we had to give up playing them.

However, there is one shining example of a stud sportswriter: Michael O’Neal, the male lead in the 1997 rom-com My Best Friend’s Wedding. O’Neal is so irresistible that two ridiculously beautiful women fight over him: His bride-to-be, Kimmy Wallace, the daughter of the owner of the Chicago White Sox played by Cameron Diaz; and his longtime best friend and former fling, food critic Julianne Potter (Julia Roberts), who tries to break up their wedding.

O’Neal makes sportswriters seem perfect. First of all, he’s played by Dermot Mulroney, a man who is impossibly handsome, but in a slightly rugged way. (Mulroney presumably learned how to portray sportswriters while attending Northwestern.) Secondly, he’s a writer, which establishes him as witty and smart—but he’s not morose, like a novelist or newswriter. He instantly charms everybody he meets, and livens up dive bars in every big town and little city his job takes him to. But he’s not a party animal—his commitment to his profession establishes him as an honorable, passionate man with a flair for the romantic. Sportswriting is a “low-paying, no-respect job,” as he describes it, which forces him to spend almost all of his time on the road, generally in dingy backwater towns. But he loves it, and as we learn during the movie, when he loves things, he loves them hard.

Yet, as grateful as I am to My Best Friend’s Wedding for providing a positive image of sports media members, I have a lot of questions about O’Neal, his job, and how he ended up engaged to a doting billionaire heiress (billionheiress?).

First of All, What Exactly Is Michael’s Job?

O’Neal works for Sport Magazine, which sounds like something you’d make up if you were trying to create a fictional publication for a character in a rom-com but was, in fact, one of America’s preeminent houses for top-tier sportswriting in the middle of the 20th century. Sport folded in 2000, so it was on its way out by the time Mulroney’s character worked there in 1997, but still, making O’Neal a Sport writer gives him an air of prestige.

That said, I’m baffled by O’Neal’s job. Julianne describes him as being on the road “52 weeks a year.” He says his own fall schedule involves covering “motor sports and training camps,” presumably meaning he covers the NFL. Julianne says that his job takes him to College Station, Texas, which means he’s covered Texas A&M games. But Michael also covers professional baseball—in the movie, he’s in the middle of writing a profile of Frank Thomas. And Kimmy explains their “honeymoon” plans by saying that “if Sacramento sweeps San Antonio, we’ll start there, or Phoenix, depending on Indiana-Cleveland”—so he’s clearly an NBA writer, too. I’m not going to tell Michael how to do his job, but it’s 1997, and this movie takes place entirely in Chicago, where the Wallace family lives. Why exactly is he leaving Chicago to cover the 1997 NBA playoffs? (Julianne brings up the “if Sacramento sweeps San Antonio” line multiple times in the movie. It’s unclear why this is such a critical part of their plans—is the implication that Michael would have to cover the Kings-Spurs series if it’s not a sweep? Regardless, one thing is clear: Between this and the Kings making the NBA Finals in How to Lose a Guy in 10 Days, Sacramento is easily the most dominant NBA team in romantic comedies of the late 1990s and early 2000s.)

So, does Michael just get to write about whatever the hell he feels like? I’m a football writer who does basketball stuff in the offseason and also writes about The Bachelor and apparently romantic comedies, and even I’m like, “Wait, why is he writing about so many different things?” Michael’s travel schedule makes him sound like a beat writer, but he’s got about 50 beats, which sorta defeats the purpose of being a beat writer in the first place. And the only story he mentions writing is a profile, which would typically be written by someone who travels only occasionally.

But all the work is apparently for relatively little payoff: Jules quips about how Michael gets “copy into maybe one issue of four.” I’m baffled by all of this. I’m supposed to understand that Sport sends this 28-year-old on the road 200 nights a year, to virtually every sporting event in America, just so he could publish one article every four months? Is this just how magazines used to work back before the internet happened?

What’s Up With This Relationship?

Michael is 28, which we learn because of his pact with Julianne to get married if they’re still single when they turn 28. (As a 29-year-old, I urge platonic best friends to pick an older age than 28 for their “get married to prevent us from dying alone” pacts.) Kimmy, though, is a 20-year-old architecture student at the University of Chicago, although she’s dropping out to road-trip with Michael while he does his job.

I keep wondering: How did these two people meet? The movie establishes early on that Michael and Kimmy have little in common. Michael is at home in strange, dimly lit bars; Kimmy seems to hate every second she spends in a karaoke bar early in the movie. She’s not even really sure what to order—Michael and Julianne get margaritas, while Kimmy gets an Amstel Light, like some sort of alien from another planet attempting to imitate human behavior. Kimmy and Michael don’t seem to have any mutual friends—which is probably for the best, considering one is a college student and the other is almost 30. In fact, Kimmy doesn’t really seem to have any friends at all. Mere days before her wedding she is without a maid of honor, eventually asking Jules if she’ll fill the role; if you have to ask your fiancé’s ex-girlfriend to be your maid of honor, you have no friends (or female relatives, for that matter). I have to ask: Did Michael meet Kimmy while doing his job? It seems like the only plausible scenario that could have introduced the shut-in daughter of the White Sox’s owner to the bon vivant sportswriter, right?

And their lives together concern me. Why does Kimmy, a budding architect, have to give up her career so Michael can occasionally get stories into a declining magazine? Is Kimmy just trying to make sure Michael doesn’t meet any other hot daughters of pro sports team owners?

Does Nobody Care That This Guy Is Going to Own the White Sox?

I’d love to read the profile of Frank Thomas that O’Neal supposedly writes during his wedding weekend. He doesn’t spend a lot of time reporting the piece—he’s got a pretty full schedule of brunches, dinners, suit fittings, and romantic architectural boat cruises with his ex-girlfriend. He does go to a White Sox game, but he spends it drinking beer in the owner’s box with his new father-in-law, White Sox owner Walter Wallace. (Canonically, Bulls/White Sox owner Jerry Reinsdorf does not exist in the My Best Friend’s Wedding universe.) His Sport bosses are also in the owner’s box, hanging out. Nobody seems too concerned by the conflicts of interest inherent in O’Neal writing a profile of the best player on the team owned by his bride’s dad, or the fact that magazine editors are chumming around with the team owner.

However, O’Neal bristles at the idea that he might give up his career. He’s passionate and committed to his life as a sportswriter—he won’t even take time off for his wedding or honeymoon, and his bride-to-be is going to give up her career so she can follow him around on the road. He’s so dedicated to his career that Julianne’s big plan to destroy his upcoming marriage hinges on convincing Michael that Kimmy and her family want him to give up sportswriting and accept a cushy corner-office job doing PR for Walter’s corporate empire. Michael is devastated: Being a sportswriter is so central to his identity that he considers calling off the marriage simply because Kimmy thought it might be better for him to work for her dad than to keep doing the job he loves.

To which I have to ask: What do you think is going to happen when you marry into a billionaire family that owns a pro sports team? The movie wants to establish Michael as hardworking, earnest, and incredibly passionate about his work, but he’s also entirely unrealistic about how his life will change when he marries into this family. He romanticizes the workaday lifestyle of the itinerant sportswriter, but, if he marries this woman, he’s going to own the Chicago White Sox. Kimmy doesn’t have any brothers or sisters, as established early in the movie. That means she’s probably going to inherit the team, and he’s going to be married to her. How is Michael possibly going to continue doing his job when he owns a team in one of the leagues he’s writing about? How can you write a profile about Frank Thomas when you’re the person who can decide whether to trade Frank Thomas? He’ll probably get great access to the White Sox, but I’m pretty sure anything he writes about any other MLB team would be considered tampering.

But perhaps more importantly: Why would Michael want to continue his job? He’s going to have billions of dollars! You don’t need to grind anymore! Go drink your beloved margaritas on the beach! I love sportswriting deeply; it’s the only job I’ve ever wanted and the only job I’m qualified to do. But if my girlfriend ever inherits an MLB team, I’m sorry—you’re gonna have to find someone else to tell you who the Winners and Losers of NFL Week 13 are.