Halle Berry in Valentino

Halle won for Introducing Dorothy Dandridge. Shawls were so popular around this time but the gown doesn't need it. It's just extra froof. I love the dress without it and would have left it in the limo.

Gwyneth Paltrow

Gwyneth ALSO has a wrap, which... I can't tell if it's brown or black. Her HAIR is brown, a phase I had forgotten, and the guard behind her looks vaguely like Willem Dafoe -- as if he woke up and is shocked to learn he's method-training for a movie in which he is an usher. I kind of can't believe GOOP dressed down this much in the year  after she won, when she was back to present.

Lara Flynn Boyle

However, she was not the MOST casual.

Russell Crowe and Jodie Foster

This was around the time he had his band, and I remember when they toured, they started in Austin and I went to see him at Stubbs and Jodie Foster was there to support him. There were a ton of rumors that he was hopelessly in love with her. I fell over at one point while trying to imitate his shitty dancing. It was a fun night (in 2001, I believe, but presumably the band existed now).

Julia Roberts and Benjamin Bratt

I was weirdly invested in them as a couple. I don't know why? I just remember thinking how damned good-looking they were together, and I guess when someone wins A Major Award you hope they'll stay up with the person they brought so that all their memories aren't FOREVER TAINTED with HEARTBREAK. I'm not dramatic at all, why do you ask?

Edie Falco

More wraps, and a LOT of shiny, stretchy velvet. 

Hilary Swank

This started her Boys Don't Cry run, and it always felt to me like the messaging of her clothes was, "TOTES FEMININE!" as if they were afraid of her somehow being pigeonholed.

Heather Locklear

It's good to see Amanda Woodward, but honestly, this feels like it's a Y-back that she's wearing the wrong way around.

Tom and Charlize

NEITHER of these people has hair this long now.

Babs

This is so INVOLVED. And so strangely preppy.

Jenny McCarthy

Here is our OTHER surprise brunette, and yes, I had also forgotten about THIS phase. I don't like to waste my limited mind space on her.

Keri Russell

It's not the best haircut, no, but she DID pull it off.

Calista Flockhart

This drses looks so ... heavy. Dreary.

Cameron Diaz in Dior, and Catherine Keener

Cammy could wear that tomorrow. I wish she WOULD. 

Portia de Rossi

She looks so happy in her gigantic wrap that might as well just have been a full coat!

James Haven and Angelina Jolie

Oh yes. It's this year. You know what's coming.

Natalie Portman

Huh. 

Lucy Liu

Now THAT is more like it.

Penelope Cruz

She looks like she just rolled out of her own beach wedding.

I feel like... I am not a kiss-my-family-on-the-lips person, but they exist, and that's their choice. It's the POSE, Marty. The leaning back into it. THAT feels very spousal. (No, I don't think anything hinky was going on. I just think Angie is an odd duck in a lot of ways.)

Renee and Jim Carrey

I always forget that these two dated. Renee has not had the happiest luck with men. I wish we could just clone Stanley Tucci and distribute them.

Hugh Grant and Elizabeth Hurley

She looks very pretty, and also needed to have Judith Lieber send over a purse because that one doesn't go.

Shirley MacLaine

The kickiest of broads.

Wino Forever and Matt Damon

I also COMPLETELY COMPLETELY forgot about these two. Also, she's not wearing black! I hope Matt Damon didn't send her into a deep black-outfit spiral from which she's not recovered. He also has such a Tom Brady face to me in this photo.

Courtney Thorne-Smith

I feel like you could also have dropped Short-Haired Kate Hudson From 2017/18 into this outfit and it would have worked.

Sigourney Weaver

Always a classic.

Josh Brolin and Minnie Driver

This party was full of people who had dated. Diane Lane -- who eventually married Josh -- was also present, but I couldn't find a good photo. Minnie famously had dated Matt Damon, and Penelope Cruz dated both Tom Cruise AND Matt Damon. 

Julianne Moore

"I have never dated Matt Damon."

Bodhi and Jenna Elfman

Who knew Dharma was so prom-y.

Mariska Hargitay and Sean Hayes

Mariska looks like Sandra Bullock to me here.

Courtney Love

"Listen, bitches, never try to domesticate a ferret. Trust me."

The SATC cast

"Check, please."

The 2000 Golden Globes Had TWO Surprise Brunettes

Plus Halle and Matt and Julianne and Cammy D and MORE.