‘Cruel Intentions’ Costars Joshua Jackson And Selma Blair Reunite At 2025 Oscars

The 2025 Oscars preceded the annual Vanity Fair Oscars party, where some of the biggest names in the entertainment world gathered to celebrate and greet old friends. The event had stars like Margot Robbie, Leonardo DiCaprio, Jennifer Lawrence, and Timothée Chalamet in attendance.

The event was held on Sunday following the awards ceremony, and it was at the perfect venue for actors to reminisce about past performances. Even though many celebrities had mini reunions, one reunion stood out, Joshua Jackson and Selma Blair, co-stars of Cruel Intentions.

Joshua Jackson and Selma Blair reunite at the Oscars

More than two decades after Cruel Intentions premiered, Jackson and Blair ran into each other again at the Oscars after-party. On Monday, Blair shared a series of party photos, including one with Jackson. Another photo she posted on her Instagram stories featured Jackson standing beside her as she hugged Questlove.

Jackson explained that the reunion had been long and truly overdue, having not caught up with Blair in a very long time. He praised how great it had been to reunite with her and meet some other familiar faces during the night. Blair turned heads dressed in a sparkling silver evening gown for the evening, but Jackson kept it effortlessly cool in a shiny black tuxedo.

What were Joshua Jackson and Selma Blair’s roles in ‘Cruel Intentions?’

Released in 1999, Cruel Intentions was a scandalous teen drama and defining film of its era. Loosely adapted from the French novel Les Liaisons Dangereuses, the film followed the manipulative games of high-school step-siblings within an upper-class New York prep school.

Blair starred as Cecile Caldwell, a naive and sheltered teenager who gets caught up in the games of Kathryn Merteuil (Gellar) and Sebastian Valmont (Phillippe). Jackson played the role of Blaine Tuttle, who was openly gay and charismatic and played an important role in the film’s subplots. His character added curiosity to the manipulative web in Cruel Intentions despite not being a main character.