My Best Friend's Wedding: 7 Thoughts I Had While Rewatching The Classic Julia Roberts Rom-Com 25 Years Later

Julia Roberts, Cameron Diaz and Dermot Mulroney in My Best Friend's Wedding.
(Image credit: Sony Pictures)

I don’t think it’s a hot take to say that Julia Roberts is one of the best romantic comedy actresses to ever do it. From 1990’s Pretty Woman to this year’s (mostly) delightful Ticket to Paradise, Roberts has allowed us to suspend all real-world expectations through classics like Notting Hill and Runaway Bride. For me, though, it was My Best Friend’s Wedding. The 1997 tale of one woman willing to destroy everything in her path in the name of staking a claim on her true love hit me right in my angsty 15-year-old heart, and it’s safe to say I got my money’s worth from that VHS tape. 

But life happens — as does newer technology — and somewhere along the line, the rewatches of Julianne (Julia Roberts) desperately trying to break up her best friend Michael (Dermot Mulroney) and his fiancée Kimmy (Cameron Diaz) ceased to be. I recently decided to revisit the old favorite as it marks its 25th anniversary, and a few things struck me about My Best Friend’s Wedding. Please accompany me on this journey: 

Julia Roberts in My Best Friend's Wedding.

(Image credit: Sony Pictures)

Who Makes A Backup Plan To Get Married At 28? 

When I was 15, did I really believe 28 was spinster age? On my rewatch, I was expecting Julianne to say she and Michael made their blood pact (!) to be each other’s backup when they were at least 30, if not older. When Jules oh-so-dramatically recalled Michael’s words — “Swear, when we’re 28 if we’ve never married, we marry each other” — an unexpected “Ha!” escaped my mouth. Come to think of it, though, I got married a week before my 28th birthday, so there’s a chance this was etched somewhere deep in my psyche. 

Rupert Everett in My Best Friend's Wedding.

(Image credit: Sony Pictures)

Rupert Everett Stole This Movie As George 

All the best romantic comedies have a best friend character, but it’s not often that person steals the whole damn show. George (Rupert Everett) was the winner for me, playing the roles of Jules’ editor, best friend, moral compass, fake fiancé and hero at the very end. During the famous lunch scene, the way he can’t stop himself from joining in with the “vengeful sluts” (Rachel Griffiths and Carrie Preston) singing “Do You Know the Way to San Jose” is pure brilliance. George was granted, in my opinion, the best lines of the whole movie, including: 

  • “I can see why.” (After Jules screams that Michael loved “me for nine goddamn years! Me!”) 
  • “Death by minibar, how glamorous.” 
  • “Love to. Love the bag, love the shoes, love everything, love to.” 
  • “Maybe there won’t be marriage. Maybe there won’t be sex. But by God, there’ll be dancing.”

Rachel Griffiths and Carrie Preston in My Best Friend's Wedding.

(Image credit: Sony Pictures)

Two All-Time Classic Musical Scenes Still Hold Up 

Speaking of the lunch scene, that is just one of two all-time classic musical moments that My Best Friend’s Wedding delivers. Do people actually exist who DON’T think of this ‘90s box office hit anytime they hear “I Say a Little Prayer for You”? This whole-restaurant sing-along is made all the better by how miserable Jules and Michael look while everybody else goes off. 

The karaoke scene, as well, where Kimmy slaughters “I Just Don’t Know What to Do With Myself,” stands up 25 years later, as Cameron Diaz's character had everybody in her corner by the end of that song — even Julianne. 

Meredith looks at Derek on Grey's Anatomy.

(Image credit: ABC)

Wait, Did This Movie Inspire Two Of Grey’s Anatomy’s Most Iconic Speeches? 

Two times during my viewing of this ‘90s classic, my Grey’s Anatomy radar went off. Is it possible that the infamous words from this rom-com live in the subconsciouses of those writing for the ABC medical drama? Hear me out. Michael talking to Jules about love as they boat down the Chicago River sounds a lot like Mark Sloan’s iconic advice to Jackson Avery:

  • MICHAEL: Kimmy says if you love someone, you say it. You say it, right then, out loud. Otherwise, the moment just passes you by.
  • SLOAN: If you love someone, you tell them. Even if you're scared that it's not the right thing. Even if you're scared that it'll cause problems. Even if you're scared that it will burn your life to the ground, you say it, and you say it loud and then you go from there.

And, you can’t tell me Meredith Grey wasn’t channeling a little Julianne when these lines were uttered: 

  • JULIANNE: Choose me. Marry me. Let me make you happy.
  • MEREDITH: Pick me. Choose me. Love me.

Neither one of those situations turned out the way our heroines wanted them to, so what should that teach us about begging for love

Paul Giamatti and Julia Roberts in My Best Friend's Wedding.

(Image credit: Sony Pictures)

Paul Giamatti Came Into Our Lives Like An Advice-Wielding, Cigarette-Smoking Angel 

Remember the days of smoking indoors? What a time. This scene with Paul Giamatti as the bellman always seemed so intimate to me, the way he and Julianne share a cigarette during her moment of crisis. He imparts some wisdom before journeying off, surely to save some other weary soul.

Paul Giamatti wasn’t the only now-big name to pop up in small roles throughout this movie. I loved seeing Rose Abdoo as the seamstress, Harry Shearer as the author at George’s book reading, and Paul Adelstein as a groomsman.

My Best Friend's Wedding old email.

(Image credit: Sony Pictures)

God Bless This Time Capsule Of Email In 1997 

As Julianne committed this heinous cyber crime to get her BFF fired from his job so he’ll dump his fiancée on their wedding day, it was hilarious to see this wildly outdated email interface, where she doesn’t even type in an email address, just Michael’s boss’ name, title, and “Sport Magazine.” 

Cameron Diaz in My Best Friend's Wedding.

(Image credit: Sony Pictures)

Kimmy Is Too Good For Michael; He And Julianne Deserve Each Other 

Throughout my rewatch, I couldn’t fight one thought that kept creeping into my head — Julianne is such a terrible person! She was so patronizing to Kimmy, who went out of her way to make sure Julianne was able to spend every available moment with Michael. And the schemes to try to stop the wedding were plain evil. Michael was hardly better, openly flirting with Julianne constantly. 

Kimmy, meanwhile, was more emotionally mature than a lot of 20-year-olds, fully accepting and trusting Jules, despite her past with Michael. Kimmy also gave him her full support with his career, despite her own feelings, because she knew it was important to him. I daresay Kimmy might have been better off just letting Michael and Julianne have each other.

Dermot Mulroney and Julia Roberts in My Best Friend's Wedding.

(Image credit: Sony Pictures)

Additional Thoughts

Here are some other quick thoughts I had about My Best Friend’s Wedding

  • Shoutout to whoever had to inflate all of the balloons pictured above.
  • That is not how restaurant reviews work. “Inventive and confident”?
  • Julia Roberts is an absolute master at physical comedy. I’d forgotten how many times she gets knocked off her feet.
  • Kimmy’s license plate reads “HPY 20.” I’d never noticed that on my old VHS.
  • Jules saying being a sportswriter isn’t a grown-up job, to me, was the most offensive thing she did in this movie. 
  • Has there ever been a more graphic insult than Michael calling Jules “the pus that infects the mucus that cruds up the fungus that feeds on the pond scum”? Poetry.

Not all movies stand the test of time, but watching My Best Friend’s Wedding 25 years later was such a treat. Although I viewed it through a slightly different lens than as the teenager I once was, I remain unbothered by the more ridiculous aspects of the plot and was pleasantly surprised by some of the subtler humor in the script. If you’re like me and no longer have access to your VHS player, My Best Friend’s Wedding is available to rent or buy on Amazon’s Prime Video (opens in new tab), and if you want to make it a marathon, check out some more of Julia Roberts’ best movies

Heidi Venable
Content Producer

Mom of two and hard-core '90s kid. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.