Leelee Sobieski, Drew Barrymore, David Arquette, and Marley Shelton

Let's begin with Never Been Kissed. SO MUCH about this photo is a time capsule, from the bias cut halter gown on Leelee, to Drew's dress-over-a-dress, to the tissue-thin fabric on Marley, to both her and Drew's shoes, to David Arquette in general... it's quite something.

Drew and Nancy Juvonen

Nancy is Drew's best friend and producing partner, and they are STILL tight and working together; Nancy also married Jimmy Fallon about eight years after this. Yay for best friends.

Jessica Alba

I always, always forget she's in this movie, and I suspect she would prefer it if we all forgot the makeup situation she's found herself in here.

David Arquette and Courteney Cox

Sometimes, I'm still surprised they happened. It was as unexpected as Dewey and Gale Weathers, honestly.

Michael Vartan

This dreamboat was two years away from his role on Alias. I look at him and can still hear "La Cienega" by Ryan Adams, from a key Sydney and Vaughn scene where the romantic tension was palpable YOU ARE HOT FOR EACH OTHER JUST KISS AAAARGH.

Patrick Dempsey

P.Demps was doing a whole lot of meh in 1999, though he was soon to recur on Will & Grace and Once and Again. He was still cultivating the hair, though. Always the hair.

Katie Holmes and mom Tammy

Okay, now we are switching gears to Go. This was a big deal for Katie, I think -- it was back when she had burgeoning indie cred despite being on Dawson's Creek -- and it's interesting to me how dressed-down she is. Not that she's alone in that. Premieres were so different then. Nowadays, someone who's not even in the movie would show up in a full ball gown. (I had a Nine West leather jacket around this time that looks SO MUCH like this.) 

Lucy Liu

And this! This is not even something where you can tell what the outfit is, because the coat has the stage. She took it off inside, though...

... to reveal ARM SHEATHS. Not to be confused with usual sleeves.

Gwen Stefani

LOOK WHO IT IS. It's funny, I look back at this and think of it as the raw clay version of Gwen Stefani, but No Doubt was already a big deal by this point. Tragic Kingdom came out in 1995. And yet somehow I never recall her looking so... shlumpy?

Natalie Imbruglia

Nothing's right, Natalie. I'm torn.

Elise Neal

OMG the sheer shirt-duster! Yes, aughts babies, THESE HAPPENED.

Ione Skye

Are her shoes... furry?

James Marsden and Lisa Linde

He is unchanged.

Barry Watson

Hello, Baby 7th Heaven!

Timothy Olyphant

Hello, Baby Olyphant!

Heath Ledger

Sniffle. It's Baby Heath. That one still hurts.

Kerr Smith

But Baby Jack from Dawson's Creek is here to cheer us up.

Ron Livingston

As is Baby Office Space.

David Boreanaz

And Baby Angel.

Scott Wolf

And Baby Bailey, although that was JUST about to go off the air at this point. But Scott Wolf will always be a beautiful baby face. He will die looking 35.

Vince Vaughn

Baby Swingers, looking totally scruffy and terrible!

Molly Ringwald

This movie really did attract some curiosity, didn't it?

Desmond Askew

And whatever happened to him?!? (I'll tell you: He did a lot of bits and pieces.) I am really into his jacket, truly. I remember one night after I moved to L.A., I looked over at a stoplight and could've sworn he was driving the car next to me. But the light changed to go, and no, I'm not making that up just because of the name of the movie. I shall never know if it was or not.

Breckin Meyer and Taye Diggs

"IT'S TRAVIS BIRKENSTOCK, LADIES AND GENTLEMEN!!!"

Reese and Ryan

And, as was evidently their custom, these two look like they're arriving in a hurry and seriously displeased.

Both "Never Been Kissed" and "Go" Premiered This Week in 1999

Let's roll them into one slideshow!