Tyra Banks

"Life Size" came out a few weeks before this Oscars, so this absolutely is a thematic tie-in. Tyra knows what she's doing.

Trey Parker and Matt Stone

I FORGOT about this! We're a month after J.Lo wore that to the Grammys and a year after Gwyneth wore that to pick up her Oscar. They were nominated for "Blame Canada," which Robin Williams memorably performed at the show, but lost to a freaking boring ballad by Phil Collins (from Tarzan). I still object.

Tom and Nicole (in Dior)

I WANT to love this on Nicole, but the design of this dress is distractingly messy to me. (The fingerless gloves are an unusual touch.) I bet it felt flowy and glam on...

... but from behind it gives the impression of falling off.

Cate Blanchett

And The Lady Blanche is casually winning the jewels game here.

For a moment I thought the back had a weird flappy thing, but no, it's clearly Gwynnie's purse.

Goop in CK

This doesn't QUITE feel fancy enough for the reining statuette holder in her return to the scene.

Kate Hudson

This is absolutely her boho-adjacent vibe from the time, but it looks like it cost $40. Her extensions were probably more than that. Maybe. Well, actually...

"WHAT YOU DON'T THINK THESE LOOK NATURAL???????"

Also, it seems like a bad idea to go barefoot at this party.

Janet McTeer

I completely forgot she had broken her foot and had to haul herself around on crutches. That must have been enormously annoying, but it was her first nomination! You don't want to miss that. (It was for Tumbleweeds.)

Roberto Benigni

I also totally forgot about THIS dude. (He won the previous year.)

Julianne Moore

Very restrained. GREAT lip.

Penelope Cruz

She looks gorgeous.

Anjelica Huston

It's sort of... half Morticia Addams, half bridesmaid.

Angela Bassett

She looks super, BUT I think I would have gone simpler with the necklace. The dress has so much hanging off the bodice; that was a bit too much icing on the cupcake.

Cameron Diaz

Oh, Cam. This isn't a sexy seance.

Erykah Badu

This all seems on-brand.

Faye Dunaway

As does this.

Vanessa Williams

Every single time she appears on this site, I say, "I MISS HER ON TV." It's still true. Maybe SHE should host The Bachlor/ette, but in character as Wilhelmina Slater from Ugly Betty. There would be a LOT of impatience and eye rolls and disgust, in a way that show badly needs.

Famke Janssen

This is not formalwear. This is the decayed remains of a gown with some Gap khakis.

Richard Farnsworth

I FORGOT MATTHEW CUTHBERT WAS NOMINATED. (Also, his fiance Jewel Van Valin is dressed like Marilla, sort of.) His kind face always makes me want to cry, which is why I never watched The Straight Story. I just knew I would be a puddle. Apparently he hid a terminal cancer diagnosis throughout award season, and was in great pain which led to his death by suicide six months later at his ranch. So very sad, but how lovely that he had this moment before he left us.

Brad Pitt

This is peak Brad Pitt.

with Jennifer Aniston

This is... peak How Jennifer Aniston Liked To Dress, but not her best choice.

Uma Thurman

Uma would totally wear this today.

Drew Barrymore

I bet she ALSO would still have that.

Ashley Judd

Beautiful. The matching eye shadow might be a bit much.

Gloria Estefan

She always cheers me up.

Charlize Theron

This is a nice orange on her.

Gretchen Mol

As a person whose hair refuses to hold any style at all, I sympathize with the fact that Gretchen may not have BEGUN the evening with gym hair but certainly ended with some.

Heather Graham, Ed Burns

Glitzy!

Fiona Apple and Paul Thomas Anderson

Her malachite-like dress is fascinating. I had forgotten that their relationship was toxic, though, which I learned when I was just Googling for the basic details of when these two were together and broke up; Emily Nussbaum did a great New Yorker profile of Fiona a year ago that addresses a lot of this.

Annette Bening, Warren Beatty

Annette went through a phase where her hair always looked lightly electrocuted.

Leo and Ellen Barkin

These two almost have the SAME hair.

Denzel and Pauletta Washington

A dapper duo.

Angelina Jolie

It is crazy to think she won this here, in front of Brad Pitt and Jennifer Aniston in her more Goth phase, and five short years later EVERYTHING would be different.

NSYNC

Menswear has come so far.

Hilary Swank

This was a good look for her.

Toni Collette in Versace

This is... fine? A little boring. I look at her here, though, and wonder why she and Edie Falco never played siblings in anything.

Judi Dench

Dame Judi is always a calming sight. Informative Caption mistakenly wrote that her daughter's name is FLINTY. It is Finty. Which is still unusual but FLINTY would really have set a hard mood to match.

Faith Hill (Versace) and Mariel Hemingway

They both look very good! This Oscars was not a huge shitshow, apparently!

Mena Suvari

This is also beautiful. (This was the American Beauty year, WHOOPS Kevin Spacey didn't make it into this slideshow, DARN.)

Salma Hayek in Valentino, and Ed Norton

I'm sure Ed is just talking to her, but the photo makes it look like he's quickly checking to make sure everything is still there.

Winona Ryder

This looks GREAT on her. One thing that has never wavered is Winona's commitment to wearing black dresses.

Chloe Sevigny in YSL

VERY glam. I love it.

Heidi Klum

It's so... LINED.

Christina Ricci

Ooh, I like this on her too. It's not as severe as it may seem...

... because the back is super sexy. Brenda Walsh and Kelly Taylor should have held out for THIS version of their spring dress.

Antonio Banderas and Melanie Griffith

Yeah ,the adults, but LOOK AT YOUNG DAKOTA.

Lily Collins

And THIS is wee Lily Collins, there with dad Phil. In 20 years we can look forward to pictures of them with THEIR kids on the red carpet. "Sunrise, sunset..."

While We're Here, We Might As Well Glance at the Rest of the 2000 Oscars

WHY NOT.