Drew Barrymore

Drew presented the Video Vanguard award to Michael Jackson. Why that necessitated a platinum wig, we may never know. This was just a few months after she flashed David Letterman atop his desk. She was obviously... trying things.

Madonna

This is so SENSIBLE for Madonna. And indeed, this is about five months before she started shooting Evita, so she probably WAS trying to be aggressively sensible.

Courtney Love

Courtney Love Tries To Hold It Together.

Courtney Love Starts To Come Unglued

Courtney Love Rolls Around On The Floor.

Courtney Love Needs Help Getting Up. This has been a story in four parts.

Michael Jackson

What? You don't travel with a mime?

Alanis Morissette

I thought those were thigh-high boots or something, and then I realized they're just... pants. The 2020s have trained me to look for shenanigans that aren't there.

Claire Danes

This holds up better than I would have expected. Also, the LIPSTICK.

Sofia Coppola

Sigh. This is what Kate Moss hath wrought.

Dennis Rodman

I wonder if Lil Nas X had a Dennis Rodman Pinterest board at any point.

Bebe Buell, Liv Tyler, Mia Tyler

Whenever I complain about lighting on the red carpet, I need to remember how bad it once was.

Cheryl "Salt" James, Deidre "Spinderella" Roper and Sandra "Pepa" Denton of Salt-N-Pepa

I assume Spinderella cut it up one time.

Darius Rucker, Michael Stipe

Who would've thought that between REM and Hootie, it'd be Hootie who's out there doing more performing.

Michael Stipe

MICHAEL. NOW IS NOT THE TIME.

Dr. Dre

This photo is in here for Jessica. Support your local Bruins!

Brandy

She said the boy was hers, but whose is the jacket?

MJ

Most people, it might be weird to wear armor, but it seems pretty regular for Michael.

"Janet Jackson looks very low-key and normal," I thought to myself.

UM. This is especially awkward given... well, all the discussions that have since been had about her brother. Just... I bet she'd like this one back.

Wesley Snipes

I cannot ever see him without hearing Michael Sheen say, "There is ONLY ONE WESTLEY SNIPES." (It's a 30 Rock reference.)

Tabitha Soren

I remember thinking she had THE coolest job.

Matt Martinez and Niki Taylor

And she was THE moment.

Tim Robbins

Okay, Tim.

Chilli, T-Boz, and Lisa "Left Eye" Lopes of TLC

I believe they made this outfits out of the sails of shipwrecked boats.

Intern George

Well well, look who came to the party. Think he'll come on Sunday? HAH. They wish.

Sheryl Crow

Wow. Corporate Crow.

Anthony Kiedis, Flea, Dave Navarro, and Chad Smith

I can't.

While We're Flashing Back, Might As Well Go All The Way to the 1995 VMAs

WAIT until you get to Janet Jackson. AWKWARD.