Madonna

It's 1999, and Madonna is dressed much as you might have seen Donna Martin, minus a bunch of hair clips and spiky bits.

With Rupert Everett

Split front pants have wormed their way back, or at least they did... last year, or maybe the year before? Also, imagine Madonna wearing a zip-front sweatshirt to an event now. I cannot.

with Demi Moore

"Don't you see? You don't NEED the blouse. You can JUST make a shirt with the scarf! Let me teach you."

Demi Moore

Hope she kept that blouse, because it's BACK, and has been for a while.

Queen Latifah

She probably DID keep all of this.

SJP and Matthew Broderick

She was in the midst of season two of Sex and the City at this point, but hadn't QUITE assumed as much of the Carrie Bradshaw fashion persona in her real life.

Natasha Richardson, Liam Neeson

Well, this one is a gut punch.

Helen Gurley Brown

Of COURSE looks bright and sprightly and has great accessories.

Dr. Ruth

Of COURSE Dr. Ruth danced the night away.

Debi Mazar

She was (is?) besties with Madonna around this time, so I assume that's why she came?

Elizabeth Hurley

She's standing in front of her date Hugh Grant in this shot, but rest assured, he looks exactly like 1999 Hugh Grant.

David Blaine

Kevin JUST told a story about how he once went to ride the roller coaster at New York New York casino, and went to put his stuff in his assigned locker and found David Blaine sucking face in front of it. I THINK that trip was this year, so clearly Kevin somehow manifested this post.

Gretchen Mol

This was during her It Girl phase.

Judith Light

And THIS was a week or so before she took over the lead role in Wit on Broadway, which is why her head is shaved. All the reviews were great and were like, "DON'T GO BACK TO TV, JUDITH," as if TV is where people went to crash. Little did they know!

Willem Dafoe

However, I did NOT remember that Willem had ever buzzed off his hair.

Julianne Moore

The messy dress! The PASHMINA! They ARE partying like it's 1999.

Anna Friel

DITTO.

Kyra Sedgwick and Kevin Bacon

They look so NORMAL. By and large everyone does, actually, but for them it's more so.

Helen Mirren

Oh, Helen. You've gotten so much better at this.

Robert De Niro

The fun part about making everyone get on a ferry is that you have weird barrels in the photo backdrops. Tina Brown did not plan this very scenically.

Pierce Brosnan and Keely Shaye Smith

What a charming rogue he has always been.

Charlie Hunnam

This is SUPER early Hunnam -- he hadn't done any TV in the US yet, and was just into his stint on the UK Queer as Folk. I wonder if he was featured in the issue as an up-and-comer, or something? Otherwise this feels random. Also, do we think his zipper was broken, or like... FASHION-broken?

Lauren Bacall

"Sure, I'll hold it, why not. I love a party."

And here is the premiere issue. I couldn't find the text of Hillary's interview online, in which she famously referred to Bill's infidelities as "weaknesses" linked to his childhood; just reactions to it. (The LA Times had a scathing rebuke of her critics.). And while it also danced with politics in the George W. Bush interview -- by none other than Sentient Popped Collar Tucker Carlson -- we need to ponder that photo of Gwyneth looking like she's slithering along the floor? Did SHE want to be Catwoman? No wonder she didn't come to the party; I wouldn't have, either.

Tina Brown's Talk Magazine Launched On This Day in 1999

With Madonna in the house.