Witherspoon, who produced Crawdads, thought Smith looked familiar but had no idea about the connection they shared.
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For producer Reese Witherspoon and star Taylor John Smith, their new film Where the Crawdads Sing served as an unexpected family reunion… of sorts.

During a recent appearance on the podcast On the List With Brett Gursky, Smith recalled the mind-blowing moment when he revealed to Witherspoon that he played the love child of one of her most iconic characters, Annette from Cruel Intentions, in an unaired pilot for a TV sequel to the beloved 1999 movie.

"I didn't tell [Witherspoon] actually till two weeks ago when we were doing press all together," Smith said. "We were doing this live interview thing, it was like a 30-minute-long thing, and at the very beginning she kind of like was staring at me a little bit and she was like, 'You remind me of a guy I dated in high school.'"

Smith continued: "I was like, 'You know I played the love child of you and Ryan [Phillippe]?' And she goes, 'Oh my God, no way,' and we have this quick little conversation about it. But I held onto that, that was in my ammo cache."

Reese Witherspoon Taylor John Smith
Reese Witherspoon and Taylor John Smith
| Credit: Axelle/Bauer-Griffin/FilmMagic; Noam Galai/Getty Images

The pilot for the Cruel Intentions series was filmed in 2016, with Sarah Michelle Gellar reprising her fan-favorite role as Kathryn Merteuil, the seductive and scheming stepsister of Phillippe's Sebastian. Smith played Bash Casey, the child of Sebastian and Annette — meaning he was the result of the infamous scene in which Sebastian takes Annette's virginity. The plot of the series involved Bash finding his late father's journal and, while trying to connect with the man he never knew, getting sucked into the lies, backstabbing, and deceit that turned Cruel Intentions into one of the juiciest movies of the '90s. (NBC ultimately passed on the series, filling its time slot with This Is Us.)

Smith told On the List that the audition process was "super easy" for Cruel Intentions. "Roger Kumble obviously is amazing and the original director of the first one," he said. "And then Sarah Michelle Gellar got to come and reprise her role, which I thought was super cool… But it never got released. But it's weird because I see a bunch of stills from it. There's a scene where I'm in the shower and there's a still from that, I'm like, 'How did that end up out and the pilot's not out?'"

Alas, fans may never get to see Smith carry on Witherspoon and Phillippe's Cruel legacy — but they can watch the hilarious moment when he tells Witherspoon about their connection in the video below. (Skip to the 1:56 mark).

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