Looking Back At The Star-Studded 1999 Premiere Of ‘Cruel Intentions’

By Brent Furdyk. 4 Mar 2019 4:00 PM

It was back in 1999 that “Cruel Intentions” held its official premiere, attended by stars Reese Witherspoon, Ryan Phillippe, Sarah Michelle Gellar, Selma Blair and an amazing array of young talented stars destined to go on to big things. The movie may not have been an Oscar contender (although it did win two Teen Choice Awards, two MTV Movie Awards and the “Trashiest Trailer” honour at the Golden Trailer Awards), “Cruel Intentions” remains a beloved fan favourite that launched numerous Hollywood careers.

To mark the anniversary, the hit film will be back in theaters for one week only starting Mar. 22.

For now, take a look back on the red carpet that night 20 years ago.

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Ryan Phillippe And Reese Witherspoon
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Not only were Ryan Phillippe and Reese Witherspoon the stars of the sexy thriller, by the time the movie premiered they were on their way to the altar. They got married later the same year, in June. Sadly, this Hollywood union would not be permanent with the pair divorcing in 2007.
Sarah Michelle Gellar
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Sarah Michelle Gellar, who was already known for her role as "Buffy", continued on as a teen icon.

She was also well-known for her part in "Scooby-Doo".
Selma Blair
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One of the film's stars, Selma Blair, strikes a sophisticated pose on the red carpet. The actress, who recently made headlines by going public with her MS diagnosis, would go on to appear in such fan-favourite films as "Legally Blonde" and "Hellboy".
Tara Reid
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While these days Tara Reid is best known for battling flying finned predators in "Sharknado" sequels, her role in "Cruel Intentions" was a breakthrough for the young actress. Following on was her hilarious 1998 performance as Bunny Lebowski in "The Big Lebowski" and leading to her biggest success, "American Pie".
Jake Gyllenhaal
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While he didn't appear in the movie, Jake Gyllenhaal did attend the "Cruel Intentions" premiere. At the time, he was a relatively unknown young actor — a situation that would change dramatically two years later with the release of cult favourite "Donnie Darko".
Adrien Brody
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Another on-the-rise young actor at the "Cruel Intentions" premiere was future Oscar-winner Adrien Brody, who would make a big splash on the big screen later that same year with the release of "Summer of Sam".
David Schwimmer And Mili Avital
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By 1999, there was no hotter TV show on the air than "Friends", and star David Schwimmer walked the red carpet at the "Cruel Intentions" premiere with his then-girlfriend, Israeli model Mili Avital.
David Schwimmer And Roger Kumble
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"Friends" star David Schwimmer poses with "Cruel Intentions" director Roger Kumble. Fun fact: Schwimmer starred an L.A. production of Kumble's play "d girl", which put the playwright on the map and led to him being hired to direct "Cruel Intentions" — which he wrote in just 12 days!
Rob Thomas
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Matchbox Twenty frontman Rob Thomas was among the attendees at the film's NYC premiere.
Ivanka Trump
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Long before her father became POTUS, 17-year-old Ivanka Trump was photographed at the "Cruel Intentions" premiere.
Gaby Hoffmann
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Another 17-year-old at the premiere was Gaby Hoffman, who was in the process of transitioning from child actress in such films as "Field of Dreams" and "Sleepless in Seattle" to more adult roles.
Heidi Klum
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At the time, Heidi Klum was one of the hottest supermodels on the planet, and she lent her star power (not to mention those cheekbones!) to the "Cruel Intentions" premiere.
Selma Blair And Reese Witherspoon
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"Cruel Intentions" stars Selma Blair and Reese Witherspoon get in a little face time at the premiere party.
Mila Kunis
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Mila Kunis, then starring in the second season of Fox sitcom "That '70s Show", sported an all-black look for the "Cruel Intentions" premiere.
Taye Diggs
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Coming off the Broadway success of "Rent" and his recent role in "How Stella Got Her Groove Back", Taye Diggs was among the talented young stars on the red carpet.
Jerry O'Connell And Charlie O'Connell
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Jerry O'Connell was on hand to support brother Charlie, who portrayed Court Reynolds in the movie.
Jon Favreau
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Hot off the success of "Swingers", Jon Favreau was the darling of the indie film world when he appeared at the "Cruel Intentions" premiere. He would go on to become one of Hollywood's most sought-after directors, helming such blockbusters as "Iron Man", "Elf" and "Jungle Book".
Selma Blair And Amy Pascal
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Selma Blair hugs "Cruel Intentions" producer Amy Pascal — who would go on to be chairperson of Sony Pictures Studios.
Seth Green And Eliza Dushku
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Gellar invited her "Buffy" co-stars to the "Cruel Intentions" premiere. Here, "Buffy" actors Seth Green and Eliza Dushku are seen clowning around at the after-party.
Jessica Alba
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Rising young star Jessica Alba was on hand for the premiere; later that year, she would be cast in the lead role for James Cameron-produced Fox sci-fi drama "Dark Angel", the TV series that propelled her to stardom.
Fred Savage And Ryan Phillippe
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Former "Wonder Years" star Fred Savage is seen having a laugh with "Cruel Intentions" star Ryan Phillippe at the premiere party.
The 'Cruel Intentions' Cast
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Main cast members Selma Blair, Sarah Michelle Gellar, Reese Witherspoon and Ryan Phillippe pose together at the premiere.

Looking Back At The Star-Studded 1999 Premiere Of ‘Cruel Intentions’

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