The actor played the lead and the actress' toxic love interest in the 1999 R-rated cult teen film, which was released the year they married and made both stars famous. Over the years, both Reese and Ryan have expressed in media interviews their reluctance to show Cruel Intentions to their kids Ava Phillippe, now 22, and Deacon Phillippe, now 17, due to its mature content, which includes a sex scene between the former couple.
"You know, I haven't checked back in with them about it now that they're both of age," Ryan told E! News recently. "I don't know if it would be creepy for them, you know? In some ways, like if I were to think about watching my parents do some of the things that their parents do in that movie, it wouldn't be the most appetizing or appealing notion."
Of course, in the age of YouTube, it's likely that Ava and Deacon are at least a tiny bit familiar with the antics of Sebastian Valmont, Kathryn Merteuil and Annette Hargrove.
"You know what, I know that they've seen clips and things like on social media, that's for sure, but I don't know if they've actually watched the movie," Ryan continued. "I think it would embarrass me a little bit, you know, I still believe it very much holds up, but, it was really racy. It was really an R rated movie, heavy R."
In 2017, during an interview on the radio show Sway in the Morning, Ryan said of his kids, "I don't want them to see Cruel Intentions. It's a little too edgy. I sometimes wonder if they sneak and watch some of the things that we'd rather them not watch. Every kid does that, right?"
On the show, Ryan also performed a rap referencing the movie.
In 2018, Reese said on Watch What Happens Live With Andy Cohen that Ava and Deacon have not seen Cruel Intentions and "have no interest in seeing me in a movie...and especially seeing me and their dad, like, having sex in a movie. It's so weird."
Despite his uneasiness to have their children watch Cruel Intentions, Ryan himself thinks back fondly about his time filming the movie.
"Even after all of these years, one of the roles that stands out most to me is Sebastian in Cruel Intentions and just the license that that character gave me to kind of play and be sort of over the top," the actor told E! News. "I still cherish that part and that experience and that character."
The star's most recent project is the buddy comedy film Lady of the Manor, written and directed by Justin Long and his brother Christian Long. Ryan plays a spoiled rich guy named Tanner.
"I kind of grew up without a lot of money or without a lot of resources and so there was part of me that throughout my career has enjoyed playing rich douchebags," the actor told E! News. "It allows me to kind of, I don't know, take pity, to have fun with or make a joke out of some of those personality types. And also the guy is so immature, I think that was what was so funny to me is that he's acting like he's in his 20s, or like he's college age, and the guy's like 40 years old."
Lady of the Manor is available in select theaters and on digital and on demand now and on Blu-ray and DVD on Sept. 21.
Take a trip down memory lane and check out 20 secrets about Cruel Intentions:
—Additional reporting by Tierney Bricker