August 09, 2018
'My Best Friend's Wedding'
The Ringer's Bill Simmons, Juliet Litman, and Amanda Dobbins set off to disrupt a nuptial and rewatch the classic 1997 rom-com 'My Best Friend's Wedding,' starring Julia Roberts and Cameron Diaz and directed by P. J. Hogan.ń

Cast
Julia Roberts as Julianne Potter
Dermot Mulroney as Michael O'Neal
Cameron Diaz as Kimmy Wallace
Rupert Everett as George Downes
Rachel Griffiths as Samantha Newhouse
Carrie Preston as Mandy Newhouse
Susan Sullivan as Isabelle Wallace
Directed by: P. J. Hogan
Music by: James Newton Howard
Notes
- The movie made $21.7 million opening weekend – topping Sleepless in Seattle's record for rom-coms – and $127 million domestic, nearly $300 million worldwide.
- Bill's extensive deep dive into Julia Roberts's dating history: Liam Neeson (1988, she was 19, he was 35), Jason Patric, Dylan McDermott, Kiefer Sutherland (engaged), Lyle Lovett (married), and the legendary story of Jason Patric stealing her away from Kiefer Sutherland days before their wedding – they ran off to Ireland.
- The Kiefer Sutherland wedding was planned at 20th Century Fox's Sound Stage 14, modeled after a garden paradise. Her four bridesmaids were her makeup artist, two agents, and an actress – a red flag according to Bill.
- Bill considers this the Apex of the rom-com genre – 1997 was the top of the crescendo, and after this the genre went off a cliff. This was the first major rom-com where the lead doesn't get the guy.
- Cameron Diaz's incredible run: The Mask, She's the One, 'My Best Friend's Wedding', then There's Something About Mary. Bill argues no actress in 30 years could have pulled off the Mary role as well.
- Danny Moder (the cinematographer Julia Roberts worked with on four films) was married when they met – Julia Roberts's mom has never forgiven her.
Categories
Most re-watchable scene
- Juliet picks the karaoke scene – "I Just Don't Know What to Do with Myself" – which shows the whole range of emotion for everyone involved, with Cameron Diaz bringing her A-game.
- Amanda picks the Say a Little Prayer for You lunch scene, especially the ending where they cut back to the lobster restaurant with people wearing lobster mitts and waving their hands.
- Bill picks the bathroom fight between Julia Roberts and Cameron Diaz – two of the biggest actresses at the peak of their powers going at it.
- Other nominees: the boat scene where Julia and Dermot almost talk about their feelings and he sings "The Way You Look Tonight"; the "Choose me, marry me" speech; the Comiskey Park scene.
What aged the best?
- Julia Roberts has never looked better in a movie – all the crop tops, the hair, the fashion. You could drop her on the street right now and she would still look great.
- Cameron Diaz going toe-to-toe with Julia Roberts – rare for an actress to share the screen that effectively with the biggest star in the world.
- The ending where Julia doesn't get the guy – the first major rom-com to flip the convention.
- Chicago as a setting – used beautifully as a character in the film, and it's a White Sox movie, not a Cubs movie.
What aged the worst?
- Dermot Mulroney's job at Sport magazine – even in the late '90s it was barely a thing anymore. It was supposed to be Sports Illustrated but they probably couldn't get the rights.
- Rich girl Cameron Diaz dropping out of school at 22 to follow a sportswriter making $39K a year.
- Julia pretending she's marrying a gay guy – the whole scene is unbelievably ridiculous and does not age well.
- The forging of the email from the billionaire father-in-law's account to try to get Michael fired – absurd that she could just walk into his office and pull it up.
- The sucking-the-ring-off-Julia's-finger scene – way over the top sexual chemistry that's uncomfortable.
Casting what-ifs
- Sarah Jessica Parker turned down the Julia Roberts role because she was about to do Sex and the City.
- Calista Flockhart reportedly turned down both roles – this was peak Ally McBeal era.
- Drew Barrymore lost out to Cameron Diaz because Julia Roberts specifically pushed for Diaz.
- Jude Law turned down the Dermot Mulroney lead role.
- Ed Burns was discussed as a much better fit – he's more believable, smarter, and would have been an upgrade, though Bill argues you need someone "a little dumb" to make the movie work.
Best "that guy"
- Cameron Diaz's parents – her dad is in so many '90s movies, and her mom (Susan Sullivan) is a recognizable TV actress.
- Rachel Griffiths and Carrie Preston in the wedding party.
- Paul Giamatti makes a cameo as a bellhop who ends up having a life talk with Julia – the most empathetic he's ever been on screen.
Best "heat check" performance
- Carrie Preston – who answers the phone at the end and talks about her sister looking at the ice sculpture of David. Very small screen time but phenomenal.
- The three karaoke/helium kids who sing at the brunch – very small amount of screen time but steal the scene.
Half-assed (internet) research
- Dermot Mulroney and Julia Roberts are still very close – he presented her with the Woman of the Decade award at the Guys' Choice Awards.
- There were talks of a sequel in 2001 – producer Jerry Zucker said the concept was 'My Best Friend's Divorce' where Kimmy and Michael are on the verge of a split.
- The test audience found Julia too evil in the original cut, leading to reshoots that beefed up Rupert Everett's character.
- The original ending had Julia meeting a man played by John Corbett (pre-Sex and the City Aidan), but it didn't test well – audiences wanted more George.
- The new ending was filmed eight months after the film wrapped. Julia Roberts wore an expensive wig covering her recent pixie cut.
- Julia Roberts's six-year career drought before this film: Dying Young, Hook, The Player, 'The Pelican Brief', I Love Trouble, Ready to Wear, Something to Talk About, Mary Reilly, Michael Collins, Everyone Says I Love You.
Apex Mountain
- Julia Roberts – Bill argues this is her Apex rather than 'Pretty Woman'. 'Pretty Woman' made her a star, but this re-established her as the most bankable A+ list actress in Hollywood and set up the next five years of her career, leading to her Oscar win.
- Rupert Everett – 100% his Apex Mountain. His most mainstream performance. He later did the Madonna movie but this is the big one.
- Dermot Mulroney – never got better (or worse) for him. This was as big as it got.
- Cameron Diaz – not quite her Apex (that's There's Something About Mary), but she proves she can go toe-to-toe with the biggest star of her generation.
- Rom-coms as a genre – 1997 might be the Apex. This was the culmination and the first movie that twisted the rom-com formula. After this, the genre went off a cliff.
Picking nits
- The entire timeline: Michael calls Julianne on Wednesday night, three days before his wedding, to tell his supposed best friend he's getting married.
- Cameron Diaz's character is 20 years old and dropping out of college to follow a sportswriter. Her billionaire family is totally fine with this.
- Julianne being a New York food critic at age 28, having already written a book – it takes 20 years to get that job, and the way the movie portrays food criticism (waiters presenting plates to the critic) is completely wrong.
- The four-day wedding starting Thursday with a Sunday evening ceremony in a church. Having a brunch on Sunday morning before the wedding is asking too much of guests.
- Julia remaining the maid of honor after everything she did – she should have been escorted off the property.
- Cameron Diaz forgiving Julia at the end with a hug in the bathroom, and Michael forgiving her for sending a fake email from his father-in-law's account that tried to get him fired.
- The backup pact age of 28 – way too young. Now it would be 38.
Sequel, prequel, prestige TV or untouchable?
- Bill suggests it could be an eight-episode Netflix show – starting with her finding out he's getting married, doing the modern version with cell phones, spread over eight days. His wife would watch it.
- Juliet and Amanda agree they'd still prefer it as a movie – time limits work in its favor.
(Probably) unanswerable questions
- Was she the worst maid of honor of all time? The hosts debate how she could have been worse – basically only if she'd actually killed the bride or succeeded in stealing the husband.
- Does every woman want a perfect gay best friend? Bill's wife apparently always has.
- When did Cameron Diaz officially cut Julia Roberts out of their lives after the honeymoon? Bill thinks there's one awkward dinner when Julia is in town for a restaurant review, then they never see each other again.
- Does Julia Roberts's character die alone? Bill predicts: panic marriage within 18 months, quick divorce, second marriage with a kid, another divorce, then an AARP boyfriend.
- Did Michael and Kimmy stay married? Amanda predicts they didn't – the travel gets to be too much, he ends up working at her father's company, and it falls apart.
Who won the movie?
- Julia Roberts won the movie – this was her comeback that re-established her as the A+ list actress and set up her Oscar-winning run.
- Rupert Everett is the scene-stealer – a lasting performance that people remember.
- Cameron Diaz proved she could go toe-to-toe with Julia Roberts, which led directly to There's Something About Mary and her becoming a massive star.