Joshua Jackson and Selma Blair Have Impromptu “Cruel Intentions” Reunion at the Oscars 25 Years After the Film’s Release

Joshua Jackson and Selma Blair Reunite Over 25 Years Post ‘Cruel Intentions’

After more than 25 years since their iconic roles in the hit movie “Cruel Intentions,” Joshua Jackson and Selma Blair recently reunited at the 2025 Vanity Fair Oscar Party. The event took place at the Wallis Annenberg Center for the Performing Arts in Beverly Hills on Sunday, Mar. 2. Blair, 52, delighted fans by sharing a series of photos from the evening on her Instagram account, including a selfie with Jackson and a picture of him standing beside her as she embraced Questlove.

Jackson, 46, made a special appearance on Good Morning America on Tuesday, Mar. 4, to discuss the mid-season premiere of his ABC drama “Doctor Odyssey.” Host Lara Spencer highlighted their unexpected reunion at the Oscars, to which Jackson expressed his joy at catching up with Blair after such a long time. He described the encounter as “lovely” and mentioned having a great night mingling with various people at the star-studded event.

The pair first shot to fame with their roles in the beloved 1999 teen drama “Cruel Intentions,” a modern adaptation of the French novel “Les Liaisons dangereuses.” Blair portrayed the innocent Cecile Caldwell, while Jackson took on the role of the mischievous Blaine Tuttle, sporting a distinctive bleach-blond hairstyle typical of the ’90s era. Fast forward to now, Blair stunned in platinum blonde hair at the Oscars, accompanied by her loyal service dog, Scout, who stole the limelight and garnered attention from fellow celebrities like Patricia Clarkson and Chrissy Teigen.

Despite Blair’s battle with multiple sclerosis since 2018, she radiated elegance and strength at the event, with Scout by her side throughout the night. The actress shared her admiration for her furry companion on social media, highlighting the support and companionship Scout provided her amidst the glamorous Hollywood setting. Blair’s openness about her health journey has inspired many fans, and her positive spirit continues to shine through in her public appearances.

The lasting bond between Jackson and Blair has not gone unnoticed by fans, who continue to celebrate their reunion and shared history from “Cruel Intentions.” The film remains a classic in the hearts of many, with the actors’ performances etched in cinematic history. As they crossed paths once again at the Oscars, it served as a heartwarming reminder of the enduring friendships forged in the entertainment industry and the nostalgia evoked by revisiting past collaborations.

In a world where new faces constantly emerge in Hollywood, the reunion of Joshua Jackson and Selma Blair serves as a poignant reminder of the lasting connections formed through shared experiences in the industry. Their on-screen chemistry in “Cruel Intentions” captured the hearts of audiences worldwide, and their off-screen reunion decades later reignited fond memories for fans and rekindled the bond between two talented actors. As they continue their respective journeys in the world of entertainment, their reunion stands as a testament to enduring friendships amidst the ever-evolving landscape of show business.