While Gellar totally killed as Kathryn Merteuil, the "Marcia f--king Brady of the Upper East Side," the deliciously villainous role was a far cry from her work as the heroic "Buffy the Vampire Slayer." That, she told EW, caused a few red flags with her team.
"My reps thought it was a terrible idea for me. They were like, 'You're Buffy! People have this great idea of you -- why shatter it?" she recalled. "I was like, 'That's the point," Gellar added, saying she basically stalked the movie's director and producer until she got the part.
Phillippe recalled thinking "There's no way they can make this" when he first read the script, before he and the filmmakers began "wooing" his then-girlfriend Witherspoon to play Annette. "She loved the movie for me, but it wasn't a great part at the time for her. She helped Roger turn it into one," he said.
As for how the role evolved for Reese, she said she found "Annette too demure and too much of a woman influenced by a guy's manipulations," in the original script. "I was starting what I guess became my bigger mission in life -- of questioning why women were written certain ways on film," she added.
The casting director also revealed they also thought Brittany Murphy was the ideal Cecile, but she "she ultimately ended up not being available." She added Selma "brought something so special" to the role.
When it came time to actually shoot the movie, they were certainly pushed out of their comfort zones to film some sexually explicit dialogue and situations.
Of the movie's infamous liplock between Kathryn and Cecile, Selma said she had "never kissed a girl before" and was concerned she would be "a horrible kisser." She said her own mom asked her, after watching the movie, "Honestly, Selma, did you have to use so much tongue? That poor Sarah, she looks so delicate, and then you just have that Goliath in her mouth."
Joshua Jackson had to simulate oral sex on Eric Mabius during his very first day on set, but added there was a "playful" vibe while shooting. "That was diving into the deep end," he said.
One of the most memorable shots in the whole film involves Phillippe's nude rear end after a swim. Speaking with the magazine, it's clear he's very aware that moment made quite the impression on a lot of young, male viewers.
"I felt okay with [showing] my butt. Everybody has a butt, it's really not that graphic," he said with a laugh. "So many guys on Twitter are like, 'That's the moment I knew I was gay,' and there have been guys like, 'I behaved like Sebastian to get laid!' Which I never did."
One of the most surprising tidbits to come out of the article was learning just how expensive it was for them to license The Verve's "Bittersweet Symphony" for the movie's legendary final moments. While director Richard Kumble wrote Kathryn's comeuppance to that song, the fact that it sampled the Rolling Stones made it extremely costly.
"The song cost close to a million dollars, which was probably 10 percent of the budget," said producer Neal Moritz. "When we thought it was going to be hopeless to get, we tried 200 other songs in its place. We could not find anything even close to it. It was well worth it."