The Real Story Behind Cameron Diaz’s Cringeworthy My Best Friend’s Wedding Karaoke

Cameron Diaz in My Best Friend's Wedding.
Cameron Diaz in My Best Friend’s Wedding. Photo: ©TriStar Pictures/Courtesy Everett Collection

For its newest cover, Entertainment Weekly assembled the cast members of the iconic 1990s romantic comedy My Best Friend’s Wedding, arguably one of the best rom-coms of the era — if you ignore the fact that it’s largely 20-somethings freaking out about not being married, that is.

Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett, as well as others who worked on the film, spoke with EW for the reunion story — and they graciously shared the real story of Diaz’s cringeworthy-yet-adorable karaoke scene from the film, a truly iconic moment of relatable rom-com awkwardness that still resonates today.

As a refresher, Roberts stars in the 1997 film as Julianne, a 27-year-old who flies to Chicago to break up the wedding of her ex and best friend, Michael (Mulroney) and the 20-year-old Kimmy, played by Diaz. You see, Julianne and Michael had promised that if they were both single by the age of 28, they would get married — and she freaks out because she is about to turn 28 (lol). Thus, the rom-com shenanigans begin, and at one point, Julianne tires to embarrass Kimmy at karaoke. That backfired, of course, because even though the song was humiliating for us all, Michael was charmed.

Speaking with EW, director P.J. Hogan explained that they staged the filming of the scene as a “real karaoke song, where the lyrics appear in front of you on all the monitors.” They shot it live and “Cameron just botched her way through the song, and the worse she got, the better the scene was,” he said. Diaz added:

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. I wanted to run and hide, and Dermot kept me there. He said, “You can do it, you can do it.” In the scene I’m just staring at him the whole time because he’s looking at me like, “You’re okay. You’re not gonna die.” And I was like, “But I’m dying.”

Everett, who was not in the scene, told EW that Diaz was able to take the moment from ridiculous to “suddenly being incredibly moving” — and pointed out that it made Michael and Kimmy “fall in love more” and Julianne become more “isolated” in her plotting to ruin the relationship. That’s so rom-com!

The Story of Cameron Diaz’s My Best Friend’s Wedding Karaoke