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Reese Witherspoon and Ryan Phillippe

Mandatory Credit: Photo by Bei/Shutterstock (4374002h) Reese Witherspoon and Ryan Phillippe Premiere of Columbia Pictures' 'Cruel Intentions' 2/25/99 Los Angeles "Cruel Intentions" Reese Witherspoon and Ryan Phillippe at the premiere of Columbia Pictures' "Cruel Intentions" . Photo ® Eric Charbonneau/BEImages 9901521-22

I've never seen a couple attending the premiere of a film in which they star together look more like they had a RAGING fight in the car on the way over. (They're engaged here but not married yet; Reese is about two months pregnant here, so she may just be fighting the urge to barf.) Shout-out to the sign for Stan's Donuts there in the background; this premiere was in Westwood, where I also went to college and Stan's donuts are EXCELLENT. I wish I had a donut now. 

Sarah Michelle Gellar

Mandatory Credit: Photo by Bei/Shutterstock (4371730r) Sarah Michelle Gellar 'Cruel Intentions' Premiere February 25, 1999: Los Angeles, CA Sarah Michelle Gellar "Cruel Intentions" Premiere Mann Village Theature Photo by Eric Charbonneau ® Berliner Studio/BEImages

Smidge is serving us some prescient sheer action here, and looks VERY much like the quintessential Buffy otherwise -- which makes sense, given that they're in the middle of filming season three here. A GREAT season of Buffy, FYI, perhaps its best. (I personally think season two is the best but only because it has the best two-part episode of the entire series in my humble, AND the Angel arc is SO GOOD. Season three is also brilliant.)

Selma Blair

Mandatory Credit: Photo by Bei/Shutterstock (4371730am) Selma Blair 'Cruel Intentions' Premiere February 25, 1999: Los Angeles, CA Selma Blair "Cruel Intentions" Premiere Mann Village Theature Photo by Eric Charbonneau ® Berliner Studio/BEImages

This look on Selma is honestly elegant and classic and, while it DOES bring a lot of 1999 to the table, it's aged beautifully. I also love her in these bangs.

Selma Blair and Sean Patrick Thomas

Mandatory Credit: Photo by Bei/Shutterstock (4371730b) Selma Blair and Sean Patrick Thomas 'Cruel Intentions' Premiere February 25, 1999: Los Angeles, CA Selma Blair and Sean Patrick Thomas "Cruel Intentions" Premiere Mann Village Theature Photo by Eric Charbonneau ® Berliner Studio/BEImages

I miss Sean Patrick Thomas, but good news! Apparently he's in the Coen Brothers Macbeth that's happening (Denzel Washington is Macbeth, Frances McD is Lady MacB, and I look forward to handing over some money to see this eventually.)

Seth Green

Mandatory Credit: Photo by Bei/Shutterstock (4371730bh) Seth Green 'Cruel Intentions' Premiere February 25, 1999: Los Angeles, CA Seth Green "Cruel Intentions" Premiere Mann Village Theature Photo by Eric Charbonneau ® Berliner Studio/BEImages

Told you the Buffy cast came out. 

Seth Green and Eliza Dushku

Mandatory Credit: Photo by Bei/Shutterstock (4374002y) Seth Green and Eliza Dushku Premiere of Columbia Pictures' 'Cruel Intentions' 2/25/99 Los Angeles "Cruel Intentions" Seth Green and Eliza Dushku ("Buffy") at the premiere of Columbia Pictures' "Cruel Intentions" . Photo ® Eric Charbonneau/Berliner Studio 9901513-17

I hope this picture is tacked to the front of both of their fridges.

Alyson Hannigan & Fred Savage

Mandatory Credit: Photo by Bei/Shutterstock (4374002aa) Alyson Hannigan & Fred Savage Premiere of Columbia Pictures' 'Cruel Intentions' 2/25/99 Los Angeles "Cruel Intentions" Alyson Hannigan & Fred Savage at the premiere of Columbia Pictures' "Cruel Intentions" . Photo ® Eric Charbonneau/Berliner Studio 9901513-5

She's in a leather skirt, he's in a leather jacket, I cannot tell you how much leather we were wearing in 1999. I wore a pair of leather pants to the millenium New Year's Eve, in fact. Remember when we thought THAT might be the end of the world??! 

Mila Kunis

Mandatory Credit: Photo by Bei/Shutterstock (4371730d) Mila Kunis 'Cruel Intentions' Premiere February 25, 1999: Los Angeles, CA Mila Kunis "Cruel Intentions" Premiere Mann Village Theature Photo by Eric Charbonneau ® Berliner Studio/BEImages

She was there with Wilmer Valderrama, whose photo I forgot to download, which is a favor to him because he looked like he'd recently installed a lo-flo showerhead.

Jessica Alba

Mandatory Credit: Photo by Bei/Shutterstock (4371730av) Jessica Alba 'Cruel Intentions' Premiere February 25, 1999: Los Angeles, CA Jessica Alba "Cruel Intentions" Premiere Mann Village Theature Photo by Eric Charbonneau ® Berliner Studio/BEImages

I am VERY perplexed by this shoe choice, as these are not shoes I remember existing in 1999 as a stylish option.

Tara Reid

Mandatory Credit: Photo by Bei/Shutterstock (4374002m) Tara Reid Premiere of Columbia Pictures' 'Cruel Intentions' 2/25/99 Los Angeles "Cruel Intentions" Tara Reid at the premiere of Columbia Pictures' "Cruel Intentions" . Photo ® Eric Charbonneau/Berliner Studio 9901519-7

These are more skirts than I would have anticipated on anyone.

Mili Avital and David Schwimmer

Mandatory Credit: Photo by Bei/Shutterstock (4374002t) Mili Avital and David Schwimmer Premiere of Columbia Pictures' 'Cruel Intentions' 2/25/99 Los Angeles "Cruel Intentions" Mili Avital and David Schwimmer at the premiere of Columbia Pictures' "Cruel Intentions" . Photo ® Eric Charbonneau/Berliner Studio 9901516-23

Nice of Ross to drop by.

Jake Gyllenhaal

Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (5126950s) Jake Gyllenhaal 'Cruel Intentions' Film Premiere, New York, America - 3 Mar 1999 1999 New York, NY Jake Gyllenhaal Premiere of Cruel Intentions Photo ® Matt Baron / BEImages

And look at this fresh-faced young up-and-comer! (October Sky, his first big movie, had JUST opened the week before.)

Time To Revisit the Premiere of Cruel Intentions
Y'all, we wore a LOT of leather jackets in 1999.

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