Revisiting the 'Cruel Intentions' Hollywood Premiere for the Movie's 20th Anniversary
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Several iconic things turn 20 this year: Britney Spears’ debut album, …Baby One More Time, David and Victoria Beckham’s marriage, Crispy M&Ms, and the saliva string seen around the world. That’s right, Cruel Intentions—the racy teen drama starring Reese Witherspoon, Ryan Phillippe, and a rather wet kiss between Sarah Michelle Gellar and Selma Blair—will celebrate its 20th anniversary in March.
Yes, it’s hard to believe that the film responsible for your sexual awakening or your first celebrity crush (hi, Ryan Phillippe’s pout) is old enough to be a Beckham child. But hey, like a fine wine, the cast has aged exceptionally well. Maybe it’s finally time to do some sort of reunion movie starring the hot ghost of Sebastian? One can dream.
In honor of the film’s big birthday, here’s a look back at the 1999 red-carpet premiere in Los Angeles. Basically, everyone was a baby.
Reese and Ryan looked so loved up
Just months before the premiere of Cruel Intentions, Reese and Ryan, who met at her 21st birthday party in 1997, announced their engagement.
Seriously, does anyone remember anything else from that night besides these two?
And Ryan's cheekbones? Anyway, Reese and Ryan were married four months after this photo was taken. She gave birth to their first child, Ava, in September of that year.
Reese and Ryan held hands on the carpet
Does your heart feel all warm and fuzzy inside? Good. Then you can ignore the fact that Ryan's suit was way too big for him.
Reese was all sorts of ethereal
You can thank her soft golden curls and the ribbon situation.
Ryan's other date that night? His pout
The next time you watch Cruel Intentions, play a fun game where you drink every time Ryan's character, Sebastian, pouts. Forget Y2K, 1999 shall forever be remembered as the year of the pout.
Sarah Michelle Gellar forgot to bring Buffy's stake, but at least she looked ~glam~
SMG walked the carpet solo that year, as her love story with Freddie Prince Jr. would not begin until the following year. And speaking of 2000, her Cruel Intentions first-base lesson with Selma Blair would go on to win the MTV Movie Award for Best Kiss.
Willow showed up to support Buffy in these fire leather pants
Alyson Hannigan and SMG starred in Buffy the Vampire Slayer together for seven seasons. BRB, going to organize a Buffy marathon for this weekend just because.
Selma Blair had killer bangs
While Selma's character Cecile wore a plain lob in the film, Selma reminded everyone of the power of blunt bangs at the premiere.
Tara Reid wore a headband
From her tube top and strappy platform shoes to the metallic nail polish and exposed midrriff, Tara, who had a small role in the film, was essentially a walking billboard for 1999 style.
Wilmer Valderrama and Mila Kunis matched
No, you didn't miss secret cameos by these two in Cruel Intentions, but That '70s Show was in the thick of its first season, so it made sense for cast members to show up at the hottest events in Hollywood.
Your other first crush, Devon Sawa, looked like a dream
"Can I keep you?"— everyone to Devon Sawa, probably.
Ross brought his girlfriend
David Scwhimmer and his oversize leather jacket (hey, it was 1999) was accompanied by his Kissing a Fool costar-turned-boo Mili Avital for the premiere. They would date for another two years, while Friends would be on for another five.
Fred Savage was basically David Schwimmer 2.0
Someone send a mass text alert the next time this trend comes back.
And Seth Green was Schwimmer 3.0
It's a shame the three of them didn't take a photo together.
Meanwhile, the O'Connell bros were invited
Tag yourself: I’m one of Charlie O’Connell’s loose bangs. He's the one on the left.
Taye Diggs looked like a snack
Further proof that, like Paul Rudd and J. Lo, Taye Diggs does not age.
And Jessica Alba wore a windbreaker and looked totally cute
See? It is possible to walk the red carpet in something other than a leather jacket! 1999 was a big year for Jessica, who starred in three films, including Never Been Kissed. Her breakout role as Max in Dark Angel would forever change her career the following year.
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