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“Cruel Intentions” at 25: All the Times Sarah Michelle Gellar and Selma Blair Have Recreated Their Iconic Kiss

In the 25 years since ‘Cruel Intentions’ featured a kiss between two female costars, Sarah Michelle Gellar and Selma Blair have reminded fans of the moment

Frank Micelotta/Getty (Left-right:) Selma Blair and Sarah Michelle Gellar at the 2000 MTV Movie Awards
Frank Micelotta/Getty (Left-right:) Selma Blair and Sarah Michelle Gellar at the 2000 MTV Movie Awards

Sarah Michelle Gellar and Selma Blair’s friendship is sealed with a kiss.

Throughout the 25 years since the actresses starred in Cruel Intentions — a movie that featured an instantly iconic locking of lips between two female costars — the friends have reenacted the moment several times.

We do it all the time,” Gellar, 46, quipped of smooching her friend in a 2022 interview with PEOPLE. “I love that girl.”

The Buffy the Vampire Slayer actress added that Blair, 51, “has a very smooth, very easy face to kiss."

Related: Amazon Finally Picks Up Cruel Intentions Series That Was First Floated in 2016

Writer-director Roger Kumble's Cruel Intentions, which since its March 1999 premiere has become a cult classic, is a modern-day reimagining of the play Dangerous Liaisons (itself based on the 18th-century French novel Les Liaisons dangereuses) set on the Upper East Side of New York City.

The movie also starred Reese Witherspoon and Ryan Phillippe. Among its infamous scenes is one featuring Gellar, as Kathryn Merteuil, teaching Blair, as Cecile Caldwell, how to smooch effectively.

<p>Sony</p> (Left-right:) Selma Blair and Sarah Michelle Gellar in "Cruel Intentions"

Sony

(Left-right:) Selma Blair and Sarah Michelle Gellar in "Cruel Intentions"

At the 2000 MTV Movie Awards, the two actresses won the prize for Best Kiss. As is tradition, Gellar — who also won for Best Female Performance at the ceremony — and Blair took to the stage to accept their popcorn trophies and recreate the kiss for the crowd.

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But that’s far from the last time that Gellar and Blair, who remain close friends in the year since, have reminded fans of the iconic smooch.

In 2020, just in time for the anniversary of Cruel Intentions, the MTV Movie & TV Awards: Greatest of All Time show crowned the duo with the Legendary Lip Lock title.

In a clip to commemorate the award, Blair reflected on how their sultry moment has impacted countless fans, particularly in the LGBTQ+ community. "I think the reason the kiss has resonated with people so long is not just for the initial shock value," she said, "but because it was a catalyst for so many young people to help them realize certain aspects of their sexuality and help make people comfortable to be who they really are."

Seeing two women share an intimate moment “represented a paradigm shift to a new dynamic towards acceptance in pop culture," said Gellar, before adding, "Well, also it was super-hot." The two then teased recreating the kiss for the camera, only to reveal a pane of glass separated them following safe social-distancing practices amid the COVID-19 pandemic.

Also in 2020, the old costars shared a photo of Blair planting a smooch on Gellar’s masked face. The “birthday kisses,” as Gellar wrote in a post, were to honor Blair’s 48th.

Related: Sarah Michelle Gellar Says Daphne and Velma Had a 'Steamy' Kiss Scene That Was Cut from 'Scooby-Doo'

Rich Polk/E! Entertainment/NBC (Left-right:) Sarah Michelle Gellar and Selma Blair at the 2022 People's Choice Awards
Rich Polk/E! Entertainment/NBC (Left-right:) Sarah Michelle Gellar and Selma Blair at the 2022 People's Choice Awards

The Legally Blonde actress has even gone so far as to evoke the smooch with a cardboard cutout of Gellar. Leaving a Los Angeles estate sale in 2021 where she had apparently purchased a life-sized depiction of the actress as Buffy Summers, Blair wrote in an Instagram post, “Sometimes you have to stop and kiss the girl you love."

Gellar also extended the kiss’ legacy in the "Taste So Good" music video for Cann and Weedmaps' 2023 Pride Month campaign, in which she starred with Kesha, Patricia Arquette, Gus Kenworthy, Vincint and several RuPaul’s Drag Race alumni. Hayley Kiyoko and Kerri Colby reenacted the Cruel Intentions moment with a can of Cann.

The “key” to capturing the essence of her iconic kiss with Blair, Gellar told PEOPLE at the time, is “you've got to get the spit. That's the hardest part.”

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