2000: Michelle, Beyonce, Kelly, and Farrah

I'm doing this chronologically, and Diana Ross wasn't until 2001, so we're going to start with a throwback to when Destiny had four children, and they all wore matching shoes and prints. (Beyonce, I can see your nipples.)

2000: Chloe Sevigny

"UGH, you GUYS, I lost the key to my chastity belt and NO ONE will come change the locks at this hour."

2000: Naomi

We've seen a lot of throwback dresses that feel like they inspired Kate Hudson's from How To Lose a Guy in 10 Days. I definitely include this one.

2000: Ashley Judd

This is really intricate and cool, marred only by its intent on cutting off her boob circulation

Sandra Bernhard

Speaking of circulating boobs, here are these. (Sandra hosted, so I'm guessing this was meant to be a statement, or... a gag, or something.)

2001: Sandra Bernhard

Still, I think someone got a talking-to.

2001: Diana Ross

HELLO. I was not going to make you wait for this any longer. She took a lot of pictures with Bob Mackie so I assume he contributed to this razzle-dazzle, and GOOD ON HIM. She looks awesome.

2001: Jimmy Fallon

Sigh. Well, but he was raw clay at this point, really.

2001: Heidi Klum

I almost didn't recognize her, and I think hr dress is actually really neat. I'd LOVE it if she wore something like that now.

2001: Parker Posey and Heather Graham

The caption for this sincerely made me laugh: "Heather Graham in Christian Dior and Parker Posey, carrying a bag from The Strand bookstore." That is... what more can I say? Well, other than that Heather's Dior looks like Marimekko joined a Circus of Fug

2001; Naomi Campbell

This is soothingly well done.

2001: Rhea Durham

"Gee," you might think, "if that goes low enough for the vee to stab her navel, maybe she's wearing it backward."

2001

NOPE. And I am not into her leather butt shield.

2002, Angela Bassett

This is a better take on that basic concept.

2002: Penelope Cruz in Ralph Lauren

Those sleeves must have been so annoying all night.

2002: Ali MacGraw

This MAY have been Kors? She looks good, and the turquoise is a super touch.

2002: Milla Jovovich

This looks like she's wearing both the drawing of a room, and then also part of a chair that's in it.

2002: Julianna Margulies

Effective.

2002: Shalom Harlow

INEFFECTIVE.

2002: Hilary Swank

This doesn't look like it fits her, entirely? It feels borrowed. From someone else, not just from a designer.

2002: Alicia Silverstone

This IS made from sheets, right? I

2002: Kyra Sedgwick

And this, from a pillowcase.

2002: Diane von Furstenberg

Oh my GOD, Diane. Was she starting a cult at this time, by any chance?

2002: Christina Ricci

This was better lost to the sands of time.

2002: Hillary Clinton

"Oh dear God they look even bigger now that I'm here and I see that NOBODY ELSE is wearing a 1984 prom dress."

2003: Rachel Weisz

That's an average dress on an above-average person.

2003: Alan Cumming

He could wear that now. Hell, I hope he found it in 2016 and has just been wearing it all day in the approximately 43 years since.

2003: Jaime King

VERY beach wedding.

2003: Karolina Kurkova

Just... watch that window, kid.

2003: Anna Wintour

Tennis dress on the top, allergens on the bottom

2003: Claire Danes in I THINK Zac Posen

Nifty enough. This, by the way, is in the year when she stopped dating Ben Lee and started seeing Billy Crudup, who left 7-months pregnant Mary Louise Parker for Claire. Also, did you know she's banned in the Philippines for some truly heinous remarks? That was... a surprise.

2003: Sarah Jessica Parker

"I thought it was my HEART that would grow three sizes on Christmas, but apparently not."

2003: Eve

This fits EVEN WORSE. This is the most mammarially damaging of all.

2003: Liya Kebede

Simple and stunning -- those earrings are a great pick.

2003: Renee Z

This is something she could as easily have worn this year on her Oscar run.

2003: Alek Wek

Her smile is SO infectious. She always just radiates joy at these things.

2003: Jane Krakowski

Get ready for more FACTS: She was nominated for a Tony when she was just 20, AND she originated Dinah the Dining Car in Starlight Express on Broadway when she was only 18. She's very decorated for theatre, workshopped the Kira role in the Xanadu musical (but didn't stay with the show), and -- ahem -- "at the 2000 American Comedy Awards, Krakowski won rave reviews when she performed a sexually charged musical tribute and love letter to Microsoft chairman, Bill Gates." LEARNING. Also I had completely forgotten she was on Ally McBeal. ALSO you can tell she's a dancer.

2003: Kristin Davis

She looks great. Also, talk about someone who keeps her life private. She was on an incredibly high-profile TV show for years and it spawned two movies, and I know almost nothing about her -- I had to take to Wikipedia to find out about her philanthropy, for example, and that she has two adopted kids. I guess this is timely because she's also now hosting a FOX reality show calld Labor of Love about a woman trying to find someone to father her child, or something? The woman was apparently at ND while I was there. Sigh.

2004: Kristin Davis

And here she is again, wearing VERY costly velvet upholstery that was earmarked for someone's penthouse living room chairs.

2004: SJP

Wow she is... burnished. And possibly wearing a bathing suit.

2004: Martha

Trust Martha to pop by in a dramatic cropped coat.

2004: Natalie Portman

That's... interesting, at least, but it also feels like a '70s migraine.

2004: Selma Blair

I feel very strongly that I love this.

2004: Heidi Klum

She had JUST had a baby. By which I mean: She had the baby in May sometime, and this is early June. I wonder if this was her first night out.

2004: Eve

This looks like a vintage-store spree that went awry

2004: Beyonce

Even Beyonce, I think, knows this was a canary catastrophe.

2005: Claire Danes

The dress is okay; her head looks great.

2005: Eva Mendes

This is like the blotchy misshapen cousin of one Julianna Margulies wore earlier in the slideshow.

2005: Linda Evangelista

Those pants are too long -- on HER; they would be a mile long on me -- but she looks lik a super cool spy.

2005: Gretchen Mol

Her rib-band matches the carpet.

2005: Nicole Richie

I wish she'd just made it cocktail-length

Sarah Michelle Gellar

I bet those necklaces thwapped at her ALL night.

2005: Emmy Rossum

Tweeeeeeee.

2005: Heidi and Seal

Heidi was nonstop pregnant. She had Leni in May 2004, a son in Sept 2005 -- so she's pregnant here -- and another one in 2006 (and then took a break until 2009 which is an eternity by comparison). Her womb must have been TIRED. 

2005: Iman

I love you, Iman, but that floppy floopy bodice is UNWORTHY.

CFDAs 2000-2005: Enter Ms. Ross

Looking DIVINE.